International Union of Pure and Applied Chemistry

Division VIII Chemical Nomenclature and Structure Representation Division

Nomenclature of Organic Chemistry. IUPAC Recommendations

and Preferred Names 2013.
Prepared for publication by Henri A. Favre and Warren H. Powell,
Royal Society of Chemistry, ISBN 978-0-85404-182-4
School of Biological and Chemical Sciences, Queen Mary University of London,
Mile End Road, London, E1 4NS, UK

Prepared by Dr G P Moss <g.p.moss@qmul.ac.uk>

All noted corrections have been incorporated in this version. Otherwise the text is as close to the
printed book as possible.

Contents

Section Title
MEMBERSHIP OF THE IUPAC COMMISSION ON
NOMENCLATURE OF ORGANIC CHEMISTRY (CNOC) (1993-
2001)
MEMBERSHIP OF THE IUPAC DIVISION OF CHEMICAL
NOMENCLATURE AND STRUCTURE REPRESENTATION
(2002-2013)
PREFACE
ACKNOWLEDGEMENTS
CHANGES FROM THE 1979 EDITION, THE 1993 GUIDE, AND
OFFICIAL PUBLICATIONS FROM 1993 THROUGH 2002
!
INCLUDED IN THE 2013 EDITION OF THE IUPAC
NOMENCLATURE OF ORGANIC CHEMISTRY, 2013 EDITION
1. Scope of the recommendations in the 2013 edition !
2. Skeletal replacement (‘a’) nomenclature !
3. Substitutive nomenclature !
4. Multiplicative nomenclature !
5. Hydro or dehydro prefixes !
6. Suffixes !
7. Prefixes !
8. Locants !
9. Acyclic systems !
10. Hantzsch-Widman system !
11. Polycyclic ring systems !
12. Seniority !
13. Adducts !
14. Enclosing marks !
15. Esters !
16. Amides !
17. Inorganic parent structures !
18. Radicals and ions !
 19. Isotopically modified compounds !
GLOSSARY !
!
P-1 GENERAL PRINCIPLES, RULES, AND CONVENTIONS
P-10 Introduction
P-11 Scope of nomenclature for organic compounds
P-12 Preferred, Preselected, and Retained IUPAC Names
P-12.1 Preferred IUPAC Names
P-12.2 Preselected Names
P-12.3 Retained Names
P-12.4 Methodology
P-13 Operations in Nomenclature of Organic Compounds
P-13.1 The Substitutive Operation
P-13.2 The Replacement Operation
P-13.3 The Additive Operation
P-13.3.1 By an additive prefix
P-13.3.2 By an additive suffix
P-13.3.3 By a separate word
P-13.4 The Subtractive Operation
P-13.4.1 By a suffix
P-13.4.2 By a change in ending
P-13.4.3 By the prefixes ‘dehydro’ and ‘nor’
P-13.5 The Conjunctive Operation
P-13.5.1 By placing a multiplicative prefix ‘bi’, ‘ter’, ‘quater’, etc.
P-13.5.2 By juxtaposition of component names (conjunctive nomenclature)
P-13.5.3 Ring formation
P-13.6 The Multiplicative Operation
P-13.7 The Fusion Operation
P-13.8 Operations Used Only in the Nomenclature of Natural Products
P-13.8.1 By the prefixes ‘de’ and ‘des’
P-13.8.2 By the prefix ‘anhydro’
P-14 General Rules
P-14.0 Introduction
P-14.1 Bonding Number
P-14.1.1 Definition
P-14.1.2 Standard bonding numbers
P-14.1.3 Nonstandard bonding numbers (λ-convention)
P-14.2 Multiplicative Prefixes
P-14.2.1 Basic multiplicative prefixes
P-14.2.2 Numerical terms for compound or complex features
P-14.2.3 Multiplicative prefixes for naming assemblies of identical units
P-14.3 Locants
 P-14.3.1 Types of locants
P-14.3.2 Position of locants
P-14.3.3 Citation of locants
P-14.3.4 Omission of locants
P-14.3.5 Lowest set of locants
P-14.4 Numbering
P-14.5 Alphanumerical Order
P-14.5.1 Simple prefixes
P-14.5.2 The name of a prefix for a substituent
P-14.5.3 When an alphanumerical ordering is required
P-14.5.4 When two or more prefixes consist of identical Roman letters
P-14.6 Nonalphanumerical Order
P-14.7 Indicated and ‘Added Indicated’ Hydrogen
P-14.7.1 Indicated hydrogen
P-14.7.2 ‘Added indicated hydrogen’
P-14.8 Adducts
P-14.8.1 Organic adducts
P-14.8.2 Mixed organic – inorganic adducts
P-15 Types of Nomenclature
P-15.0 Introduction
P-15.1 Substitutive Nomenclature
P-15.1.1 Parent hydrides
P-15.1.2 Functional parent compounds
P-15.1.3 Suffixes
P-15.1.4 Position of the endings ‘ane’, ‘ene’, and ‘yne’
P-15.1.5 Prefixes and their order in names
P-15.1.6 Other components of substitutive names
P-15.1.7 Construction of substitutive names
P-15.1.8 Substitution rules for parent structures with retained names
P-15.2 Functional Class Nomenclature
P-15.2.0 Introduction
P-15.2.1 Functional class nomenclature using substituent group names
P-15.2.2 Functional class nomenclature using functional modifiers
P-15.2.3 Seniority of functional classes
P-15.2.4 Polyfunctional compounds
P-15.3 Multiplicative Nomenclature
P-15.3.0 Introduction
P-15.3.1 General methodology
P-15.3.2 Construction of multiplicative names
P-15.3.3 Identical structural units linked by unsymmetrical multiplicative groups
P-15.3.4 Limitations of multiplicative nomenclature
P-15.4 Skeletal Replacement (‘a’) Nomenclature
 P-15.4.0 Introduction
P-15.4.1 General rules
P-15.4.2 Skeletal replacement (‘a’) nomenclature
P-15.4.3 Skeletal replacement (‘a’) nomenclature for acyclic parent hydrides
P-15.5 Functional Replacement Nomenclature
P-15.5.1 Definition
P-15.5.2 General methodology
P-15.5.3 Scope of functional replacement nomenclature
P-15.6 Conjunctive Nomenclature
P-15.6.1 Name formation
P-15.6.2 Limitations of conjunctive nomenclature
P-15.6.3 Analysis of conjunctive name construction
P-16 Name Writing
P-16.0 Introduction
P-16.1 Spelling
P-16.2 Punctuation
P-16.2.1 Commas
P-16.2.2 Full stops
P-16.2.3 Colons and semicolons
P-16.2.4 Hyphens
P-16.2.5 Spaces
P-16.3 Multiplicative prefixes ‘di’, ‘tri’, etc. vs. ‘bis’, ‘tris’, etc.
P-16.3.1 Multiplicative prefixes
P-16.3.2 General methodology
P-16.3.3 The basic numerical prefixes ‘di’, ‘tri’, ‘tetra’, etc.
P-16.3.4 Parentheses (round brackets)
P-16.3.5 The numerical prefixes ‘bis’, ‘tris’, ‘tetrakis’, etc.
P-16.3.6 The prefixes ‘bis’, ‘tris’, ‘tetrakis’, etc.
P-16.4 Other Numerical Terms
P-16.4.1 The numerical prefixes ‘bi’, ‘ter’, ‘quater’, etc.
P-16.4.2 The prefix ‘mono’
P-16.4.3 The term ‘sesqui’
P-16.5 Enclosing Marks
P-16.5.1 Parentheses (also called curves or round brackets)
P-16.5.2 Brackets (also called square brackets)
P-16.5.3 Braces (also called curly brackets)
P-16.5.4 Multiple types of enclosing marks
P-16.6 Italicization
P-16.6.1 Lower case italic letters
P-16.6.2 Italicized elements symbols, such as O, N, As
P-16.6.3 The italic element symbol H
P-16.6.4 Italic terms, syllables, and capital Roman letters
 P-16.7 Elision of Vowels
P-16.7.1 Vowels systematically elided
P-16.7.2 There is no elision of terminal vowels
P-16.8 Addition of Vowels
P-16.8.1 For euphonic reasons (the vowel ‘o’)
P-16.8.2 For euphonic reasons (the letter ‘a’)
P-16.9 Primes
P-16.9.1 Primes (′), double primes (′′), triple primes (′′′), etc., with nitrogen
P-16.9.2 Superscript arabic numbers,
Primes (′), double primes (′′), triple primes (′′′), etc., with superscripted
P-16.9.3
numerical locants
Primes (′), double primes (′′), triple primes (′′′), etc., used to differentiate
P-16.9.4
identical locants
P-16.9.5 Other uses of primes
P-16.9.6 Multiple primes

P-2 PARENT HYDRIDES

P-20 Introduction
P-21 Mononuclear and Acyclic Polynuclear Parent Hydrides
P-21.1 Mononuclear Parent Hydrides
P-21.1.1 Mononuclear parent hydrides with standard bonding numbers
P-21.1.2 Mononuclear parent hydrides with nonstandard bonding numbers
P-21.2 Acyclic Polynuclear Parent Hydrides
P-21.2.1 Hydrocarbons
Homogeneous acyclic parent hydrides other than hydrocarbons and
P-21.2.2
boron hydrides
P-21.2.3 Heterogenous acyclic parent hydrides
Acyclic parent hydrides containing heteroatoms with nonstandard
P-21.2.4
bonding numbers
P-22 Monocyclic Parent Hydrides
P-22.1 Monocyclic Hydrocarbons
P-22.1.1 Saturated monocyclic hydrocarbons
P-22.1.2 Unsubstituted monocyclic hydrocarbon polyenes
P-22.1.3 Parent hydrocarbons having retained names
P-22.2 Heteromonocyclic Parent Hydrides
P-22.2.1 Retained names of heteromonocycles
Heteromonocyclic parent hydrides with 3-10 membered rings
P-22.2.2
(Hantzsch-Widman names)
Heteromonocyclic parent hydrides named by skeletal replacement (‘a’)
P-22.2.3
nomenclature
Heteromonocycles with eleven or more members with the maximum
P-22.2.4
number of noncumulative double bonds
P-22.2.5 Homogeneous monocyclic parent hydrides other than boron hydrides
P-22.2.6 Heteromonocyclic parent hydrides composed of repeating heterounits
 Heteromonocyclic parent hydrides having heteroatoms with nonstandard
P-22.2.7
bonding numbers
P-23 Polyalicyclic Parent Hydrides (Extended von Baeyer System)
P-23.0 Introduction
P-23.1 Definitions and Terminology
P-23.2 Naming and Numbering of von Baeyer Hydrocarbons
P-23.2.1 Selection of the main ring
P-23.2.2 Naming bicyclic alicyclic hydrocarbons
P-23.2.3 Numbering bicyclic alicyclic hydrocarbons
P-23.2.4 Selection of the main bridge
P-23.2.5 Naming and numbering tricyclic alicyclic hydrocarbons
P-23.2.6 Naming and numbering polyalicyclic hydrocarbons
P-23.2.6.1 Naming polycyclic alicyclic hydrocarbons
P-23.2.6.2 Selection of the main bridge and secondary bridges
P-23.2.6.3 Numbering of secondary bridges
P-23.2.6.4 If there is a further choice for numbering the secondary bridges
P-23.3 Heterogeneous Heterocyclic von Baeyer Parent Hydrides
P-23.3.1 Heterogeneous heterocyclic von Baeyer systems
P-23.3.2 When there is a choice for numbering
P-23.4 Homogeneous Heterocyclic von Baeyer Parent Hydrides
Heterogeneous Heterocyclic von Baeyer Parent Hydrides Composed of
P-23.5
Alternating Heteroatoms
Heterogeneous von Baeyer systems composed of alternating skeletal
P-23.5.1
heteroatoms
P-23.5.2 The prefixes ‘Si-’ or ‘N-’ preceded by the italic number ‘1’
P-23.5.3 Silasesquioxanes, silasesquithianes, etc.
Heterocyclic Polyalicyclic Parent Hydrides having Heteroatoms with
P-23.6
Nonstandard Bonding Numbers
P-23.6.1 The λ-convention
P-23.6.2 When there is a choice for numbering
P-23.7 Retained Names for von Baeyer Parent Hydrides
P-24 Spiro Ring Systems
P-24.0 Introduction
P-24.1 Definitions
P-24.2 Spiro Ring Systems with only Monocyclic Ring Components
P-24.2.0 Introduction
P-24.2.1 Monospiro alicyclic ring systems
P-24.2.2 Linear polyspiro alicyclic ring systems
P-24.2.3 Branched polyspiro alicyclic ring systems
P-24.2.4 Heterocyclic spiro ring systems
Monospiro Ring Systems Containing Two Identical Polycyclic Ring
P-24.3
Components
P-24.3.1 Monospiro ring systems consisting of two identical polycyclic ring
 components
Where appropriate the maximum number of noncumulative double
P-24.3.2
bonds
P-24.3.3 If there is a choice for assigning primed locants
Heterocyclic ‘spirobi’ ring systems named by skeletal replacement (‘a’)
P-24.3.4
nomenclature
Dispiro Ring Systems with Three Identical Polycyclic Ring Components
P-24.4
Spirofused Together
P-24.4.1 Dispiro ring systems with three identical polycyclic ring components
P-24.4.2 If there is a choice for locants
P-24.4.3 Three identical heterocyclic ring components spirofused together
Monospiro Ring Systems with Different Components, at least One of
P-24.5
which is a Polycyclic Ring System
P-24.5.1 Monospiro ring systems with different ring components
Monospiro ring systems with different ring components at least one
P-24.5.2 being a polycyclic ring and at least one ring component requiring the use
of skeletal replacement (‘a’) nomenclature
P-24.5.3 Alphanumerical order
P-24.5.4 Ring systems modified by skeletal replacement (‘a’) nomenclature
Unbranched Polyspiro Ring Systems with Different Components, One
P-24.6
being a Polycyclic Ring System
P-24.6.1 If there is a choice of locants
P-24.7 Branched Polyspiro Ring Systems
A central ring component is spirofused to three or more identical
P-24.7.1
terminal ring components
Two or more different terminal ring components spirofused to a central
P-24.7.2
component
P-24.7.3 If no decision can be attained by application of P-24.7.2
Additional components are spiro-fused to a branched polyspiro
P-24.7.4
compound
Spiro Ring Systems Containing Atoms with Nonstandard Bonding
P-24.8
Numbers
P-24.8.1 Spiro ring systems with only monocyclic ring components
P-24.8.2 Monospiro ring systems with two identical polycyclic ring components
Spiro ring systems with three identical components and one nonstandard
P-24.8.3
spiro atom
Monospiro ring systems with different ring components, at least one of
P-24.8.4
which is a polycyclic ring with a nonstandard spiro atom
Unbranched polyspiro ring systems with different ring components, at
P-24.8.5 least one of which is a polycyclic ring with at least one nonstandard spiro
atom
P-24.8.6 Branched spiro ring systems with at least one polycyclic ring component
P-25 Fused and Bridged Fused Ring Systems
P-25.0 Introduction
P-25.1 Names of Hydrocarbon Parent Ring Components
P-25.1.1 Retained names for hydrocarbons
 P-25.1.2 Systematically named hydrocarbon parent components
P-25.1.2.1 Polyacenes
P-25.1.2.2 Polyaphenes
P-25.1.2.3 Polyalenes
P-25.1.2.4 Polyphenylenes
P-25.1.2.5 Polynaphthylenes
P-25.1.2.6 Polyhelicenes
P-25.1.2.7 Ace...ylenes
P-25.2 Names of Heterocyclic Parent Ring Components
P-25.2.1 Retained names for heterocycles
P-25.2.2 Systematically named heterocyclic components
P-25.2.2.1 Heteromonocyclic parent components
P-25.2.2.2 Heteranthrene components
P-25.2.2.3 Pheno...ine components
P-25.2.2.4 Heteromonocyclic components fused to a benzene ring
P-25.3 Constructing Fusion Names
P-25.3.1 Definitions, terminology, and general principles
P-25.3.2 Constructing two-component fusion names
P-25.3.3 Numbering of fused ring systems
P-25.3.4 Constructing polycomponent fusion names
P-25.3.4.1 Three types of fusion names
P-25.3.4.2 Constructing polycomponent fusion names
P-25.3.4.2.1 Order of seniority for selecting parent components
P-25.3.4.2.2 Order of seniority for selecting attached components
P-25.3.4.2.3 Order of citation of fusion prefixes
P-25.3.4.2.4 Order of seniority of locants (letters and numbers)
P-25.3.5 Heteromonocyclics fused to a benzene ring
P-25.3.6 Identical attached components
P-25.3.7 Multiparent ring systems
P-25.3.8 Omission of locants in fusion descriptors
P-25.4 Bridged Fused Ring Systems
P-25.4.1 Definitions and terminology
P-25.4.2 Names of bridges
P-25.4.2.1 Bivalent bridges
P-25.4.2.2 Polyvalent bridges
P-25.4.2.3 Composite bridges
P-25.4.3 Naming bridged fused systems
P-25.4.4 Numbering bridge atoms
P-25.4.5 Order for numbering of bridges
Limitations of Fusion Nomenclature: Three Components ortho and peri-
P-25.5
fused Together
P-25.5.1 Skeletal replacement (‘a’) nomenclature
 P-25.5.2 Selection of a less senior hydrocarbon parent component
P-25.5.3 Use of bridging nomenclature
Fused Ring Systems with Skeletal Atoms with Nonstandard Bonding
P-25.6
Numbers
P-25.7 Double Bonds, Indicated Hydrogen, and the δ-Convention
P-25.7.1 Indicated hydrogen
P-25.7.2 The δ-convention
P-25.8 Parent Components in Decreasing Order of Seniority (Partial Lists)
Partial list of heterocyclic parent components in decreasing order of
P-25.8.1
seniority
Partial list of hydrocarbon parent components in decreasing order of
P-25.8.2
seniority
P-26 Phane Nomenclature
P-26.0 Introduction
P-26.1 Concepts and Terminology
P-26.1.1 Simplification and amplification
Simplified skeleton of the phane parent hydride, simplified phane parent
P-26.1.2
graph, simplified skeletal name, and skeletal locants
P-26.1.3 Superatom and superatom locants
P-26.1.4 Amplificant, amplification prefix, and amplificant locants
P-26.1.5 Attachment atoms and attachment locants
P-26.1.6 Phane parent skeleton, phane parent name, and phane parent hydrides
P-26.2 Components of Phane Parent Names
P-26.2.1 Simplified skeletal names
P-26.2.2 Amplification prefixes
P-26.2.3 Multiple identical amplificants
P-26.3 Superatom Locants and Amplificant Attachment Locants
P-26.3.1 Superatom locants
P-26.3.2 Attachment locants
P-26.4 Numbering of Phane Parent Hydride
P-26.4.1 Numbering of phane parent skeletons and amplificants
Numbering of simplified phane skeletons with respect to amplificant
P-26.4.2
numbering
P-26.4.3 Numbering of phane parent hydrides
P-26.5 Skeletal Replacement (‘a’) Nomenclature in Phane Nomenclature
P-26.5.1 Skeletal replacement (‘a’) nomenclature in simplified phane names
P-26.5.2 Skeletal replacement (‘a’) nomenclature in amplificants
Simultaneous skeletal replacement (‘a’) in simplified skeletal names and
P-26.5.3
amplificants
P-26.5.4 Numbering of heterophane parent hydrides with respect to heteroatoms
P-26.6 Other Aspects of Phane Nomenclature
P-27 Fullerenes
P-27.0 Introduction
 P-27.1 Definitions
P-27.1.1 Fullerenes
P-27.1.2 Fulleranes
P-27.1.3 Fulleroids
P-27.2 Fullerene Names
P-27.2.1 Systematic names
P-27.2.2 Trivial names
P-27.2.3 Preferred IUPAC names
P-27.3 Numbering of Fullerenes
P-27.4 Structurally Modified Fullerenes
P-27.4.0 Introduction
P-27.4.1 Homofullerenes
P-27.4.2 Norfullerenes
P-27.4.3 Secofullerenes
P-27.4.4 Cyclofullerenes
P-27.4.5 Combination of structure-modifying operations
P-27.5 Replacement of Skeletal Atoms
Fullerenes in which carbon atoms have been replaced by one or more
P-27.5.1
heteroatoms
When ‘homo’, ‘nor’, ‘seco’, or ‘cyclo’ prefixes co-occur with skeletal
P-27.5.2
replacement terms, such as ‘oxa’ or ‘aza’
P-27.6 Addition of Rings and Ring Systems to Fullerenes
P-27.6.1 Fullerenes ortho fused to organic rings or ring systems
P-27.6.2 Bridged fullerenes
P-27.6.3 Spiro fullerenes
P-27.7 Other Aspects of Fullerene Nomenclature
P-28 Ring Assemblies
P-28.0 Introduction
P-28.1 Definitions
P-28.2 Ring Assemblies of Two Identical Cyclic Systems
P-28.2.1 Ring assemblies with a single bond junction
P-28.2.2 Ring assemblies with a double bond junction
P-28.2.3 Indicated hydrogen of components in two-component ring assemblies
Unbranched Ring Assemblies of Three through Six Identical Cyclic
P-28.3
Systems
Unbranched ring assemblies consisting of three or more identical cyclic
P-28.3.1
systems
Exceptions to the use of parent hydride names, ring assemblies of three
P-28.3.2
through six benzene rings
Ring Assemblies Composed of Identical Cyclic Systems Modified by
P-28.4
Skeletal Replacement (‘a’) Nomenclature
P-28.4.1 Assemblies composed of identical heterocyclic compounds
Since hydrocarbon ring assemblies are the parent structures for the
P-28.4.2
application of skeletal replacement (‘a’) nomenclature
 P-28.5 Ring Assembles Composed of More than Six Identical Cyclic Systems
P-28.6 Branched Ring Assemblies of Identical Cyclic Systems
P-28.7 Ring Assemblies of Nonidentical Cyclic Systems
P-29 Prefixes Denoting Substituent Groups Derived from Parent Hydrides
P-29.0 Introduction
P-29.1 Definitions
P-29.1.1 A simple substituent group
P-29.1.2 A compound substituent group
P-29.1.3 A complex substituent group
P-29.2 General Methodology for Naming Substituent Groups Prefixes
Systematic Prefixes for Simple Substituents Groups Derived from
P-29.3
Saturated Parent Hydrides
P-29.3.1 Substituent prefixes derived from mononuclear parent hydrides
P-29.3.2 Substituent prefixes derived from acyclic parent hydrides
P-29.3.3 Substituent prefixes derived from saturated cyclic parent hydrides
P-29.3.4 Substituent prefixes derived from mancude parent hydrides
P-29.3.5 Substituent prefixes derived from ring assemblies
P-29.3.6 Substituent prefixes derived from phane systems
P-29.4 Compound Substituent Groups
P-29.4.1 Compound substituted substituent groups
P-29.4.2 Compound catenated substituent groups
P-29.5 Complex Substituent Groups
P-29.5.1 Complex substituted substituent groups
P-29.5.2 Concatenated complex substituent groups
Retained Names for Prefixes of Simple Substituent Groups Derived from
P-29.6
the Parent Hydrides Described in Chapter P-2
P-29.6.1 Retained prefixes that are preferred prefixes
P-29.6.2 Retained prefixes that are not used as preferred prefixes
P-29.6.3 Retained prefixes no longer recommended as approved prefixes

P-3 CHARACTERISTIC (FUNCTIONAL) AND SUBSTITUENT GROUPS

P-30 Introduction
P-31 Modification of the Degree of Hydrogenation of Parent Hydrides
P-31.0 Introduction
Substituent Groups Derived from Parent Hydrides with ‘ene’ or ‘yne’
P-31.1
endings
P-31.1.1 General methodology
P-31.1.2 Acyclic parent hydrides
P-31.1.3 Monocyclic parent hydrides
P-31.1.4 Bi- and polycyclic von Baeyer parent hydrides
P-31.1.5 Spiro compounds
P-31.1.6 Phane parent hydrides
P-31.1.7 Ring assemblies of unsaturated components
 P-31.2 Substituent Groups Modified by the Prefixes ‘hydro’ or ‘dehydro’
P-31.2.1 The prefixes ‘hydro/dehydro’
P-31.2.2 General methodology
P-31.2.3 The prefix ‘hydro’
Modification of the degree of hydrogenation of monocyclic
P-31.2.3.1
mancude compounds
P-31.2.3.2 Names of saturated heteromonocyclic compounds
P-31.2.3.3 Saturation of double bonds in polycyclic mancude compounds
Retained names of partially saturated polycyclic mancude
P-31.2.3.3.1
compounds
P-31.2.3.3.2 Polycyclic mancude compounds
P-31.2.3.3.3 Spiro compounds
P-31.2.3.3.4 Phane compounds
P-31.2.3.3.5 Ring assemblies
P-31.2.4 The prefix ‘dehydro’
Prefixes for Substituent Groups Derived from Parent Hydrides with
P-32
a Modified Degree of Hydrogenation
P-32.0 Introduction
Substituent Groups Derived from Parent Hydrides with ‘ene’ or ‘yne’
P-32.1
endings
P-32.1.1 Substituents derived from unsaturated acyclic compounds
P-32.1.2 Monocyclic substituent groups
Substituent groups derived from parent hydrides having a fixed
P-32.1.3
numbering
P-32.2 Substituent Groups Modified by the Prefix ‘hydro’
P-32.2.1 For heteromonocyclic parent hydrides
P-32.2.2 For polycyclic mancude compounds
P-32.2.3 With added indicated hydrogen
Retained Names for Substituent Groups Derived from Unsaturated
P-32.3
Acyclic Parent Hydrides
Retained Names for Substituent Groups Derived from Partially Saturated
P-32.4
Polycyclic Parent Hydrides
P-33 Suffixes
P-33.0 Introduction
P-33.1 Definitions
P-33.2 Functional Suffixes
P-33.2.1 Basic functional suffixes
P-33.2.2 Derived preferred and preselected suffixes
P-33.3 Cumulative Suffixes
P-34 Functional Parent Compounds
P-34.0 Introduction
P-34.1 Retained Functional Parent Compounds
Organic functional parent compounds (arranged by characteristic
P-34.1.1
group class)
 P-34.1.2 Organic functional parent compounds (arranged alphabetically)
Organic functional parent compounds for general and specialized
P-34.1.3
nomenclature
P-34.1.4 Inorganic functional parent compounds
P-34.2 Substituent Groups Related to Functional Parent Compounds
P-34.2.1 Organic substituent groups (arranged by classes)
P-34.2.2 Organic substituent groups (arranged alphabetically)
Substituent group names derived from organic compounds used in
P-34.2.3
general and specialized nomenclature
P-34.2.4 Preselected substituent group names
P-35 Prefixes Corresponding to Characteristic Groups
P-35.0 Introduction
P-35.1 General Methodology
P-35.2 Simple Prefixes Denoting Characteristic Groups
P-35.2.1 Retained traditional prefixes
Substituents formed by subtracting one or more hydrogen atoms from
P-35.2.2
mono and dinuclear parent hydrides
P-35.2.3 Simple prefixes derived from functional parent compounds
P-35.3 Compound Substituent Prefixes
Names of compound prefixes derived from suffixes or functional
P-35.3.1
parent compounds by substitution
Names of compound prefixes derived from suffixes or functional
P-35.3.2
parent compounds by concatenation
P-35.4 Complex Substituent Prefixes
P-35.4.1 Complex substituent prefixes by substitution
P-35.4.2 Complex substituent prefixes by concatenation
P-35.5 Mixed Substituent Prefixes
Mixed substituent prefixes names using substitutive and additive
P-35.5.1
operations

P-4 RULES FOR NAME CONSTRUCTION

P-40 Introduction
P-41 Seniority Order for Classes
P-42 Seniority Order for Acids
Class 7a. Acids Expressed by Suffixes (Excludes Carbonic and
P-42.1
Polycarbonic acids)
P-42.2 Class 7b. Carbon Acids with no Substitutable Hydrogen Atoms
Class 7c. Noncarbon Acids having Substitutable Hydrogen Atoms on the
P-42.3
Central Atom
Class 7d. Noncarbon Acids used to Generate Derivatives having
P-42.4
Substitutable Hydrogen Atoms
P-42.5 Class 7e. Other Monobasic ‘oxo’ Acids used as Functional Parents
P-43 Seniority Order for Suffixes
P-43.0 Introduction
 P-43.1 General Methodology of Functional Replacement
P-44 Seniority order for parent structures
P-44.0 Introduction
P-44.1 Seniority Order for Parent Structures
Maximum number of substituents corresponding to the principal
P-44.1.1
characteristic group
P-44.1.2 Senior atom in accordance with the seniority of classes
P-44.1.3 Seniority order only for rings and ring systems
P-44.1.4 Seniority among acyclic chains (the principal chain)
P-44.1.5 Other criteria
P-44.2 Seniority Order only for Rings and Ring Systems
P-44.2.1 General criteria (other than phanes)
P-44.2.1.1 General methodology
P-44.2.1.2 A heterocycle
P-44.2.1.3 At least one nitrogen ring atom
At least one heteroatom (in the absence of nitrogen) that occurs earlier
P-44.2.1.4
from a list
P-44.2.1.5 The greater number of rings
P-44.2.1.6 Greater number of skeletal atoms
P-44.2.1.7 Greater number of heteroatoms of any kind
P-44.2.1.8 Greater number of heteroatoms that occur earlier from a list
P-44.2.2 Criteria specific to a particular kind of ring or ring system
P-44.2.2.1 Monocycles
P-44.2.2.2 Polycyclic systems
P-44.2.2.2.1 Spiro ring systems
P-44.2.2.2.2 Cyclic phane systems
P-44.2.2.2.3 Fused ring systems
P-44.2.2.2.4 Bridged fused ring systems
P-44.2.2.2.5 Von Baeyer ring systems
P-44.2.2.2.6 Linear (acyclic) phanes
P-44.2.2.2.7 Ring assemblies
P-44.3 Seniority of Acyclic Chains (the Principal Chain)
P-44.3.1 Greater number of acyclic heteroatoms of any kind
P-44.3.2 Greater number of skeletal atoms
P-44.3.3 Greater number of the most senior acyclic heteroatom
P-44.4 Seniority Criteria Applicable to Rings, Ring Systems, or Acyclic Chains
If P-44.1 through P-44.3, does not effect a choice of senior parent
P-44.4.1
structure
P-44.4.1.1 Greater number of multiple bonds
P-44.4.1.2 Greater number of double bonds
P-44.4.1.3 One or more atoms with nonstandard bonding numbers
P-44.4.1.4 Lowest locants for indicated hydrogen
P-44.4.1.5 Lower locants for heteroatoms introduced by skeletal replacement
 (‘a’) nomenclature as a set
Lower locants for heteroatoms introduced by skeletal replacement
P-44.4.1.6
(‘a’) nomenclature in the order
P-44.4.1.7 Lower locant(s) for carbon atoms at fusion sites
P-44.4.1.8 Lower locants for characteristic groups cited as a suffix
P-44.4.1.9 Lowest locants for points of attachment (if a substituent group)
P-44.4.1.10 Lowest locants for endings or prefixes that express changes in the
degree of hydrogenation,
i.e., for ‘ene’ and ‘yne’ endings and ‘hydro/dehydro’ prefixes
P-44.4.1.11 One or more isotopically modified atoms
P-44.4.1.12 One or more stereogenic centers
P-45 Selection of the Preferred IUPAC Name
P-45.0 Introduction
P-45.1 Multiplication of Identical Senior Parent Structures
P-45.1.1 Multiplicative nomenclature is senior to substitutive nomenclature
P-45.1.2 Choice between two or more parent structures
P-45.2 Criteria Related to Number and Location of Substituent Groups
P-45.2.1 Maximum number of substituent groups cited as prefixes
P-45.2.2 Lower locant set for substituent groups cited as prefixes
P-45.2.3 Lower locant set for substituent groups in order of citation in the name
Criteria Related only to Substituents with Nonstandard Bonding Numbers,
P-45.3
other Criteria being Equal
Maximum number of substituent group(s) with the higher bonding
P-45.3.1
number cited as prefixes
Lower locant set for substituent group(s) with the higher bonding
P-45.3.2
number cited as prefixes
P-45.4 Criteria Related only to Isotopic Modification of Substituents
Senior parent structure that has the lowest locant(s) for isotopically
P-45.4.1
modified substituent groups
Senior parent structure that has the lowest locant(s) for nuclides of
P-45.4.2
higher atomic number
Senior parent structure that has the lowest locant(s) for nuclides of
P-45.4.3
higher mass number
P-45.5 Criteria Related to Alphanumerical Order of Names
P-45.5.1 Earlier in alphanumerical order
P-45.5.2 When names based on alphanumerical order are the same
P-45.6 Criteria Related only to Configuration
P-45.6.1 Introduction
P-45.6.2 General principles
P-45.6.3 Alphabetic order of the stereochemical descriptors ‘R’ and ‘S’
P-45.6.4 Application of CIP sequence rules 4 and 5
P-46 The Principal Chain in Substituent Groups
P-46.0 Introduction
P-46.1 The Principal Substituent Chain
 P-46.1.1 Greater number of heteroatoms
P-46.1.2 Greater number of skeletal atoms
P-46.1.3 Greater number of heteroatoms in a set order
P-46.1.4 Greater number of multiple bonds, then double bonds
P-46.1.5 One or more atoms with nonstandard bonding numbers
P-46.1.6 Lowest locants for heteroatoms
P-46.1.7 Lowest locants for heteroatoms appearing first a set order
Lowest locants for free valences of any kind in the order ‘yl’ > ‘ylidene’
P-46.1.8
> ‘ylidyne’
P-46.1.9 Lowest locant(s) for multiple bonds, then double bonds
P-46.1.10 Lowest locant(s) for (an) atom(s) with nonstandard bonding number(s)
P-46.1.11 Greatest number of substituents of any kind
P-46.1.12 Lowest locants for substituents
Lowest locants for the substituent(s) cited earlier in alphanumerical
P-46.1.13
order
P-46.2 Principal Substituent Chains in Isotopically Labeled Compounds
P-46.2.1 Greater number of isotopically modified atoms
Greater number of nuclides of higher mass number or isotopically
P-46.2.2
modified substituent atoms or groups
P-46.3 Principal Substituent Chains in Compounds with Stereogenic Centers
P-46.3.1 Greater number of (Z)-double bonds
P-46.3.2 Greater number of (R)-chirality centers

P-5 SELECTING PREFERRED IUPAC NAMES AND

CONSTRUCTING NAMES OF ORGANIC COMPOUNDS
P-50 Introduction
P-51 Selecting the Preferred Type of IUPAC Nomenclature
P-51.0 Introduction
P-51.1 Selecting the Preferred Type of Nomenclature
P-51.1.1 Substitutive nomenclature is preferred to functional class nomenclature
P-51.1.2 Substitutive nomenclature is preferred to conjunctive nomenclature
Skeletal replacement (‘a’) nomenclature is preferred to substitutive
P-51.1.3
nomenclature
Skeletal replacement (‘a’) nomenclature is preferred to multiplicative
P-51.1.4
nomenclature
Multiplicative nomenclature is preferred to simple substitutive
P-51.1.5
nomenclature
P-51.2 Functional Class Nomenclature
Characteristic groups with preferred IUPAC names using functional
P-51.2.1
class nomenclature
P-51.2.2 Functional class nomenclature for general nomenclature
P-51.3 Multiplicative Nomenclature
P-51.3.1 Preferred IUPAC multiplicative names
P-51.3.2 When more than two identical parent structures occur in the structure
 P-51.3.3 When conditions (1), (2), and (3) as defined in P-53.3.1 are not met
P-51.4 Skeletal Replacement (‘a’) Nomenclature
P-51.4.1 Skeletal replacement (‘a’) nomenclature in acyclic chains
P-51.4.2 Skeletal replacement (‘a’) nomenclature for cyclic compounds
P-51.5 Conjunctive Nomenclature vs. Substitutive Nomenclature
Selecting Preferred IUPAC Names and Preselected Names for Parent
P-52
Hydrides
P-52.1 Selecting Preselected Names
P-52.1.1 Mononuclear parent hydride names
P-52.1.2 Preselected names for homogeneous acyclic polynuclear parent hydrides
P-52.1.3 Preselected names for heterogeneous acyclic parent hydrides
Preselected names for parent hydrides with nonstandard bonding
P-52.1.4
numbers
P-52.1.5 Heteromonocyclic noncarbon Hantzsch-Widman parent hydrides
P-52.1.6 Heterocyclic noncarbon von Baeyer and spiro compounds
Preselected names for homogeneous and heterogeneous heterobi- and
P-52.1.7
heteropolycyclic fused ring systems
P-52.2 Selecting Preferred IUPAC Names
P-52.2.1 Acyclic and monocyclic hydrocarbons
P-52.2.2 Heteroacyclic and heteromonocycles
Unsaturated heteromonocyclic compounds with more than ten ring
P-52.2.3
members
P-52.2.4 Preferred IUPAC names in fusion nomenclature
P-52.2.4.1 Five-membered ring requirement
P-52.2.4.2 Heteromonocycles as components in fusion names
Multiparent fused ring systems with three or more interparent
P-52.2.4.3
components
P-52.2.4.4 Limitations to fusion nomenclature
P-52.2.5 Preferred IUPAC names in phane nomenclature
Preferred IUPAC names for (C60-Ih)[5,6]fullerene and (C70-
P-52.2.6
D5h(6))[5,6]fullerene with ‘nor’ or ‘seco’ prefixes
P-52.2.7 Preferred IUPAC names and numbering for ring assemblies
P-52.2.8 Selection between a ring and a chain as parent hydride
P-53 Selecting Preferred Retained Names of Parent Hydrides
Selecting the Preferred Method for Modifying the Degree of
P-54
Hydrogenation
P-54.1 Methods for Modifying the Degree of Hydrogenation of Parent Hydrides:
P-54.2 Unsaturated Monocyclic Carbocycles
Unsaturation in Ring Assemblies Composed of Mancude and Saturated
P-54.3
Rings
P-54.4 Names Modified by ‘hydro’ or ‘dehydro’ Prefixes
P-54.4.1 Hantzsch-Widman heteromonocycles
P-54.4.2 Saturated heteromonocyclic compounds
P-54.4.3 Fused ring systems and monocyclic mancude ring assemblies
 P-54.4.4 Names modified by ‘dehydro’ prefixes
Selecting the Preferred Retained Name for Functional Parent
P-55
Compounds
P-56 Selecting the Preferred Suffix for the Principal Characteristic Group
P-56.1 The Suffix ‘peroxol’ for -OOH
P-56.2 The Suffixes ‘SO-thioperoxol’, and Chalogen Analogues
P-56.3 The Suffixes ‘imidamide’ and ‘carboximidamide’
P-56.4 The Endings ‘diyl’ and ‘ylidene’ vs. ‘ylene’
P-57 Selecting Preferred and Preselected Prefixes for Substituent Groups
P-57.1 Prefixes Derived from Parent Hydrides
P-57.1.1 Prefixes derived from mononuclear and acyclic parent hydrides
P-57.1.2 Retained names used as preferred prefixes
P-57.1.3 Retained prefixes recommended only for general nomenclature
P-57.1.4 Retained prefixes no longer recommended
P-57.1.5 Prefixes derived from cyclic parent hydrides
Prefixes derived from parent hydrides with modified degrees of
P-57.1.6
hydrogenation
P-57.2 Prefixes Derived from Characteristic (functional) Groups
P-57.3 Prefixes Derived from Organic Functional Parent Compounds
P-57.4 Construction of Linear Compound and/or Complex Substituent Prefixes.
P-58 Selecting Preferred IUPAC Names
P-58.1 Introduction
Indicated Hydrogen, ‘Added Indicated Hydrogen’, and Nondetachable
P-58.2
Hydro Prefixes
P-58.2.1 Indicated hydrogen
P-58.2.2 ‘Added indicated hydrogen’
Specific rules related to indicated hydrogen, ‘added indicated hydrogen’
P-58.2.3
and hydro prefixes
P-58.2.4 Prefix nomenclature
P-58.2.5 Nondetachable hydro prefixes vs. indicated hydrogen
P-58.3 Homogeneous Hetero Chains and Functional Groups
Preselected names for unbranched homogeneous heteroacyclic parent
P-58.3.1
hydrides
Atoms expressed by a principal characteristic group, a functional parent
P-58.3.2
compound, or a compulsory prefix
P-59 Name Construction
P-59.0 Introduction
P-59.1 General Methodology
P-59.1.1 Determine the type(s) of nomenclature and operations to be used
P-59.1.2 Determine the type(s) of nomenclature and operations to be used
P-59.1.3 Select the parent hydride(s)
P-59.1.4 Name the parent hydride, and the principal characteristic group
P-59.1.5 Determine affixes and/or prefixes
 Name substituent groups and characteristic groups not cited as principal
P-59.1.6
characteristic groups as prefixes
P-59.1.7 Assemble the components into a complete name
Complete the name with all required descriptors for stereochemical
P-59.1.8
features
P-59.1.9 Characteristic groups
P-59.1.10 Numbering nomenclatural features
P-59.2 Examples Illustrating the General Methodology
P-59.2.1 Selection of parent hydrides
P-59.2.2 Seniority of heteroatoms over suffixes
P-59.2.3 Seniority of principal characteristic groups over unsaturation
Seniority of 'ene' and 'yne' endins and hydro prefixes over detachable
P-59.2.4
prefixes
P-59.2.5 Treatment of detachable prefixes

P-6 APPLICATIONS TO SPECIFIC CLASSES OF COMPOUNDS

P-60 Introduction
P-60.1 Topical Outline
P-60.2 Presentation of Names
P-61 Substitutive Nomenclature: Prefix Mode
P-61.0 Introduction
P-61.1 General Methodology
P-61.2 Hydrocarbyl Groups and Corresponding Di- and Polyvalent Groups
P-61.2.1 Acyclic hydrocarbons
P-61.2.2 Cyclic hydrocarbons
P-61.2.3 Hydrocarbons consisting of rings and chains
P-61.2.4 Structures containing heterocycles
P-61.3 Halogen Compounds
P-61.3.1 Halogen atoms in its standard bonding number
P-61.3.2 Halogen atoms attached to heteroatoms
P-61.3.3 Compounds containing the group –I(OH)2 or similar groups
P-61.3.4 Retained names
P-61.4 Diazo Compounds
P-61.5 Nitro and Nitroso Compounds
P-61.5.1 Nitro and nitroso compounds
P-61.5.2 Nitro attached to heteroatoms
P-61.5.3 aci-Nitro compounds
P-61.6 Heterones
P-61.7 Azides
P-61.8 Isocyanates
P-61.9 Isocyanides
P-61.10 Fulminates and Isofulminates
P-61.11 Polyfunctional Compounds
 P-61.11.1 Low locants assigned as a set
P-61.11.2 Low locants assigned to the prefix cited first in the name
P-62 Amines and Imines
P-62.0 Introduction
P-62.1 General Methodology
P-62.2 Amines
P-62.2.1 Primary amines
P-62.2.2 Secondary and tertiary amines
P-62.2.3 The prefix ‘amino’
P-62.2.4 Polyamines
P-62.2.5 Multiplicative nomenclature
P-62.2.6 Modification of the degree of saturation/unsaturation of amines
P-62.3 Imines
P-62.3.1 Substitutive names for imines
P-62.4 N-Substitution of Amines and Imines by Heteroatoms
P-62.5 Amine Oxides, Imine Oxides, and Chalcogen Analogues
P-62.6 Amine and Imine Salts
P-62.6.1 Cation and anion names
P-62.6.2 Salts of indefinite structure (adducts)
Hydroxy Compounds, Ethers, Peroxols, Peroxides, and Chalcogen
P-63
Analogues
P-63.0 Introduction
P-63.1 Hydroxy Compounds and Chalcogen Analogues
P-63.1.1 Retained names
P-63.1.2 Systematic names of alcohols, phenols, enols, and ynols
P-63.1.3 Heterols
P-63.1.4 Substitutive nomenclature, prefix mode
P-63.1.5 Sulfur, selenium and tellurium analogues of hydroxy compounds
P-63.2 Ethers and Chalcogen Analogues
P-63.2.1 Definitions and general methodology
P-63.2.2 Names of substituent groups R′-O–, R′-S–, R′-Se–, and R′-Te–
P-63.2.3 Retained names of ethers
P-63.2.4 Systematic names of ethers
Names of chalcogen analogues of ethers, i.e., sulfides, selenides, and
P-63.2.5
tellurides
P-63.3 Peroxides and Chalcogen Analogues
P-63.3.1 Peroxides, disulfides, diselenides, and ditellurides
P-63.3.2 Mixed chalcogen analogues of peroxides
P-63.4 Hydroperoxides (Peroxols) and Chalcogen Analogues
P-63.4.1 Hydroperoxides
P-63.4.2 Chalcogen analogues of hydroperoxides
P-63.5 Cyclic Ethers, Sulfides, Selenides, and Tellurides
 P-63.6 Sulfoxides and Sulfones
P-63.7 Polyfunctional Compounds
Salts of Hydroxy Compounds, Hydroperoxy Compounds and Their
P-63.8
Chalcogen Analogues
P-63.8.1 Neutral salts of hydroxy compounds and their chalcogen analogues
P-63.8.2 Cyclic salts are named as heterocycles
P-63.8.3 Partial salts of polyols and their chalcogen
P-64 Ketones, Pseudoketones, Heterones, and Chalcogen Analogues
P-64.0 Introduction
P-64.1 Definitions
P-64.1.1 Ketones
P-64.1.2 Pseudoketones and heterones
P-64.2 Ketones
P-64.2.1 Retained names
P-64.2.2 Systematic construction of names for ketones
P-64.2.2.1 Acyclic ketones
P-64.2.2.2 Cyclic ketones
P-64.2.2.3 Seniority order for numbering
P-64.2.2.4 Ketenes
P-64.3 Pseudoketones
P-64.3.1 Cyclic anhydrides, esters and amides
P-64.3.2 Acyclic pseudoketones
P-64.4 Heterones
P-64.4.1 Acyclic heterones
P-64.4.2 Thioketone and thioaldehyde oxides
P-64.5 Carbonyl Groups as Prefixes
P-64.5.1 Ketones
P-64.5.2 Pseudoketones
P-64.6 Chalcogen Analogues of Ketones, Pseudoketones, and Heterones
P-64.6.1 Chalcogen analogues of ketones, pseudoketones and heterones
P-64.6.2 Seniority order of suffixes
P-64.7 Polyfunctional Ketones, Pseudoketones and Heterones
P-64.7.1 Ketones, pseudoketones and heterones, and their chalcogen analogues
There is no seniority order difference between ketones and
P-64.7.2
pseudoketones
When an oxygen atom of a ketone, pseudoketone, or heterone is
P-64.7.3
replaced by a sulfur, selenium or tellurium atom
P-64.8 Acyloins
P-65 Acids, Acyl Halides and Pseudohalides, Salts, Esters, and Anhydrides
P-65.0 Introduction
P-65.1 Carboxylic Acids and Functional Replacement Analogues
P-65.1.1 Retained names
P-65.1.2 Systematic names
 P-65.1.2.1 Carboxylic acid groups
P-65.1.2.2 The suffix ‘carboxylic acid’
P-65.1.2.3 Seniority order for numbering
P-65.1.2.4 Polyfunctional carboxylic acids
Carboximidic, carbohydrazonic, carbohydroximic, and carbohydroxamic
P-65.1.3
acids
P-65.1.3.1 Carboximidic acids
P-65.1.3.2 Carbohydrazonic acids
P-65.1.3.3 Carbohydroximic acids
P-65.1.4 Peroxycarboxylic acids
P-65.1.5 Chalcogen analogues of carboxylic acids
P-65.1.5.1 Functional replacement in systematic names of carboxylic acids
P-65.1.5.2 Functional replacement in retained names of carboxylic acids
P-65.1.5.3 Functional replacement in peroxycarboxylic acids
P-65.1.6 Amic, anilic, and aldehydic acids
P-65.1.7 Acyl groups derived from carboxylic and related acids
P-65.1.7.1 Definitions and name formation
Carboxylic acids having retained names that are preferred IUPAC
P-65.1.7.2
names
P-65.1.7.3 Carboxylic acids with names retained only for general nomenclature
P-65.1.7.4 Systematically named carboxylic acids
P-65.1.7.5 Mixed acyl groups
P-65.1.8 Formic acid
P-65.2 Carbonic, Cyanic, and Di- and Polycarbonic Acids
P-65.2.1 Carbonic acid
P-65.2.2 Cyanic acid
P-65.2.3 Di-, tri-, tetra-, and polycarbonic acids
Sulfur, Selenium, Tellurium Acids with Chalcogen Atoms Directly
P-65.3
Linked to a Parent Hydride
P-65.3.0 Introduction
P-65.3.1 Substitutive nomenclature, suffix mode, for sulfonic, sulfinic, etc., acid
P-65.3.2 Substitutive nomenclature, prefix mode for sulfonic, sulfinic, etc. acids
P-65.3.3 Polyfunctional compounds
P-65.4 Acyl Groups as Substituent Groups
P-65.4.1 General methodology
P-65.5 Acyl Halides and Pseudohalides
P-65.5.1 Acyl halides from suffix acids
P-65.5.2 Acyl pseudohalides from suffix acids
Acyl halides and pseudohalides from carbonic, cyanic, and the
P-65.5.3
polycarbonic acids
P-65.5.4 Acyl halides and pseudohalides as substituent groups
P-65.6 Salts and Esters
P-65.6.1 General methodology
 P-65.6.2 Salts
P-65.6.3 Esters, lactones, and related compounds
P-65.6.3.1 Definitions
P-65.6.3.2 General methodology
P-65.6.3.3 Peferred IUPAC names for esters
P-65.6.3.3.1 Monoesters
P-65.6.3.3.2 Polyesters derived from a single acid component
P-65.6.3.3.3 Polyesters formed from a single ‘alcoholic’ component
Polyesters derived from multiple acid components and multiple
P-65.6.3.3.4
‘alcoholic’ components
P-65.6.3.3.5 Partial esters from polybasic acids and salts
Substitutive nomenclature is senior to functional class
P-65.6.3.3.6
nomenclature for preferred IUPAC names for esters
P-65.6.3.3.7 Esters of acids modified by functional replacement
P-65.6.3.4 Pseudoesters
P-65.6.3.5 Cyclic esters
P-65.6.3.6 Acylals
P-65.7 Anhydrides and Their Analogues
P-65.7.0 Introduction
P-65.7.1 Symmetric anhydrides
P-65.7.2 Mixed anhydrides
P-65.7.3 Thioanhydrides and other chalcogen analogues
P-65.7.4 Peroxyanhydrides and chalcogen analogues
P-65.7.5 Diacyl derivatives of trioxidane and chalcogen analogues
P-65.7.6 Di- and polyanhydrides
P-65.7.7 Cyclic anhydrides
P-65.7.8 Polyfunctional anhydrides
P-66 Amides, Imides, Hydrazides, Nitriles, and Aldehydes
P-66.0 Introduction
P-66.1 Amides
P-66.1.0 Introduction
P-66.1.1 Primary amides
P-66.1.1.1 Carboxamides
Sulfonamides, sulfinamides, and related selenium and tellurium
P-66.1.1.2
amides
P-66.1.1.3 Substitution of primary amides
P-66.1.1.4 Amides denoted as prefixes
P-66.1.2 Secondary and tertiary amides
P-66.1.3 ‘Hidden’ amides
P-66.1.4 Chalcogen analogues of amides
P-66.1.5 Lactams, lactims, sultams, and sultims
Amides derived from carbonic, cyanic, and the di- and polycarbonic
P-66.1.6
acids
 P-66.1.6.1 Carbonic acid and related compounds
P-66.1.6.2 Cyanic acid
P-66.1.6.3 Di- and polycarbonic acids
P-66.1.7 Polyfunctional amides
P-66.2 Imides
P-66.2.1 Acyclic imides and cyclic imides
P-66.2.2 Imide prefixes
P-66.3 Hydrazides
P-66.3.0 Definition
P-66.3.1 Systematic names
P-66.3.2 Substituent groups derived from hydrazides
P-66.3.3 Substituted hydrazides
P-66.3.4 Chalogen analogues of hydrazides
P-66.3.5 Hydrazides from carbonic, cyanic, and di- and the polycarbonic acids
P-66.3.6 Semioxamazones
P-66.4 Amidines, Amidrazones, Hydrazidines, and Amidoximes (Amide Oximes)
P-66.4.1 Amidines
P-66.4.1.1 Suffixes for amidines
P-66.4.1.2 Amidines of carbonic, and di- and polycarbonic acids
P-66.4.1.3 Prefixes for the amidine characteristic group
P-66.4.1.4 Substituted amidines
P-66.4.1.5 Formamidine disulfides
P-66.4.1.6 Diamidides
P-66.4.2 Amidrazones
P-66.4.2.1 Amidrazone suffixes
P-66.4.2.2 Amidrazones of carbonic acid and di- and polycarbonic acids
P-66.4.2.3 Amidrazone prefixes
P-66.4.3 Hydrazidines
P-66.4.3.1 Hydrazidine suffixes
Hydrazidines derived from sulfonic acid, and similar selenium and
P-66.4.3.2
tellurium acids
Hydrazidines derived from carbonic acid and di- and polycarbonic
P-66.4.3.3
acids
P-66.4.3.4 Hydrazidine prefixes
P-66.4.4 Amidoximes (amide oximes)
P-66.5 Nitriles
P-66.5.0 Introduction
P-66.5.1 Preferred names for nitriles
P-66.5.2 Substituted nitriles
Nitriles/cyanides corresponding to carbonic and di- and polycarbonic
P-66.5.3
acids
P-66.5.4 Nitrile oxides and chalcogen analogues
P-66.6 Aldehydes
 P-66.6.0 Introduction
P-66.6.1 Systematic names of aldehydes
P-66.6.2 Aldehydes from di- and polycarbonic acids
P-66.6.3 Chalcogen analogues of aldehydes
P-66.6.4 Polyfunctional aldehydes
Acetals and ketals, hemiacetals and hemiketals, and their chalcogen
P-66.6.5
analogues
Mononuclear and Polynuclear Noncarbon Acids and their Functional
P-67 Replacement Analogues as Functional Parents for Naming Organic
Compounds
P-67.0 Introduction
P-67.1 Mononuclear Noncarbon Oxoacids
P-67.1.1 Names of mononuclear noncarbon oxoacids
Functional replacement nomenclature applied to mononuclear
P-67.1.2
noncarbon oxoacids
P-67.1.2.1 Mononuclear acids modified by infixes
P-67.1.2.2 Mononuclear acids modified by prefixes
General methodology for functional replacement nomenclature using
P-67.1.2.3
infixes
Mononuclear noncarbon oxoacids modified by functional replacement
P-67.1.2.4
nomenclature
P-67.1.2.5 Acid halides and pseudohalides
P-67.1.2.6 Amides and hydrazides
P-67.1.3 Salts, esters and anhydrides of mononucleat noncarbon oxoacids
Substituent prefix groups derived from mononucleat noncarbon
P-67.1.4
oxoacids
P-67.1.4.1 Mononuclear nitrogen, phosphorus, arsenic, and antimony acids
P-67.1.4.1.1 Preselected prefixes
P-67.1.4.1.2 Substituent groups for general nomenclature
P-67.1.4.1.3 Compound and complex substituent groups
P-67.1.4.2 Substituent groups derived from boron acid and silicic acid
P-67.1.4.3 Substituent groups derived from nitric and nitrous acids
P-67.1.4.4 Substituent groups derived from chalcogen acids
P-67.1.4.5 Substituent groups derived from halogen acids
P-67.1.5 Seniority order among noncarbon oxoacids and derivatives
P-67.1.6 aci-Nitro compounds
P-67.2 Di- and Polynuclear Noncarbon Oxoacids
P-67.2.1 Preselected names
Functional replacement derivatives of di- and polynuclear noncarbon
P-67.2.2
oxoacids
Acid halides and pseudohalides of di- and polynuclear noncarbon
P-67.2.3
oxoacids
P-67.2.4 Amides and hydrazides of di- and polynuclear noncarbon oxoacids
P-67.2.5 Esters and anhydrides of di- and polynuclear noncarbon oxoacids
 P-67.2.6 Substituent groups derived from polyacids
P-67.3 Substitutive Names and Functional Class Names of Polyacids
Polynuclear noncarbon oxoacids that cannot be formed on the basis of
P-67.3.1
fundamental oxoacids
P-67.3.2 The disulfurous acid name dilemma
Nomenclature of Organic Compounds of the Group 13, 14, 15, 16, and
P-68
17 Elements not Included in Sections P-62 through P-67
P-68.0 Introduction
P-68.1 Nomenclature of Compounds of Group 13 Elements
P-68.1.1 Parent hydrides
P-68.1.2 Names for substituent groups derived from parent hydrides
P-68.1.3 Modification of the degree of hydrogenation
P-68.1.4 Functional parent compounds
P-68.1.5 Substitutive nomenclature
P-68.1.5.1 Suffix nomenclature
P-68.1.5.2 Prefix nomenclature
P-68.1.6 Adducts
P-68.1.6.1 Structures for Lewis ‘adducts’
P-68.1.6.2 General organic method for naming Lewis adducts
P-68.1.6.3 Intramolecular adducts
P-68.2 Nomenclature for Compounds of Group 14 Elements
P-68.2.0 Introducction
P-68.2.1 Silicon, germanium, tin, and lead parent hydrides
P-68.2.2 Substituent groups derived from parent hydrides
P-68.2.3 Modification of the degree of hydrogenation
P-68.2.4 Silicic acid as a functional parent compound
P-68.2.5 Substitutive nomenclature: suffix mode
P-68.2.6 Substitutive nomenclature: prefix mode
P-68.3 Nomenclature of Compounds of Group 15 Elements
P-68.3.1 Nitrogen compounds
P-68.3.1.0 Introduction
P-68.3.1.1 Hydroxylamines, oximes, and nitrolic acids and nitrosolic acids
Hydrazine and related compounds: hydrazones, azines,
P-68.3.1.2
semicarbazides, semicarbazones, and carbonohydrazides
P-68.3.1.3 Diazene and related compounds
P-68.3.1.3.1 Substitution of diazene
P-68.3.1.3.2 Azo compounds, R-N=N-R′
P-68.3.1.3.3 Azoxy compounds, R-N=N(O)-R′
P-68.3.1.3.4 Diazenecarbohydrazide, HN=N-CO-NH-NH2
P-68.3.1.3.5 Formazan, H2N-N=CH-N=NH
P-68.3.1.3.6 Carbodiazone [bis(diazenyl)methanone], HN=N-CO-N=NH
P-68.3.1.3.7 Isodiazene, R2N+=N–
P-68.3.1.4 Polyazanes
 P-68.3.2 Phosphorus, arsenic, and antimony compounds
P-68.3.2.1 General methodology
P-68.3.2.2 Parent hydrides
P-68.3.2.3 Substitutive nomenclature
P-68.3.3 Bismuth compounds
P-68.4 Nomenclature of Compounds of Group 16 Elements
P-68.4.0 Introduction
P-68.4.1 Three or more homogeneous contiguous chalcogen atoms
P-68.4.2 Three or more heterogeneous contiguous chalcogen atoms
P-68.4.3 Chalcogen parent hydrides with nonstandard bonding numbers
P-68.4.3.1 Sulfanes, selanes, and tellanes
Di- and polysulfoxides, polysulfones, and selenium and tellurium
P-68.4.3.2
analogues
Sulfimides, and chalcogen analogues, H2E=NH, where E = S, Se, or
P-68.4.3.3
Te
Sulfinylamines, RN=E=O, sulfonylamines, RN=E(=O)2 and
P-68.4.3.4
chalcogen analogues where E = S, Se, or Te
Sulfonediimines, RE(=NH)2R′ and chalcogen compounds where E =
P-68.4.3.5
S, Se, or Te
Sulfoximides, R2E(=O)=NR′ and chalcogen analogues where E = S,
P-68.4.3.6
Se, or Te
Sulfur diimides, HN=E=NH and chalcogen analogues where E = S,
P-68.4.3.7
Se, or Te)
Sulfur triimides, E(=NH)3 and chalcogen analogues where E = S, Se,
P-68.4.3.8
or Te)
P-68.5 Nomenclature of Compounds of Group 17 Elements
P-68.5.0 Substitutive nomenclature
P-68.5.1 Nomenclature based on halogen parent hydrides
P-68.5.2 Nomenclature of halogen acids
P-68.5.3 Amides of halogen acids
P-69 Nomenclature for Organometallic Compounds
P-69.0 Introduction
P-69.1 Organometallic Compounds of Elements in Groups 13, 14, 15, and 16
P-69.2 Organometallic Compounds of Elements in Groups 3 through 12
P-69.2.1 Coordination nomenclature
P-69.2.2 Definitions of terms
P-69.2.3 Compounds with at least one metal-carbon single bond
P-69.2.4 Organometallic groups with multicenter bonding to carbon atoms
Bridging organometallic groups with multicenter bonding to carbon
P-69.2.5
atoms
Organometallic compounds with unsaturated molecules and substituent
P-69.2.6
groups
P-69.2.7 ‘‘Ocenes’’
P-69.3 Organometallic Compounds of Elements in Groups 1 and 2
P-69.4 Metallacycles
P-69.5 Order of Seniority Order for Organometallic Compounds
P-69.5.1 Compounds having two identical or different metal atoms
Compounds having one metal atom of class (1) and another atom of
P-69.5.2
class (2)
For organometallic compounds having two metal atoms belonging to
P-69.5.3
class (2)

P-7 RADICALS, IONS, AND RELATED SPECIES

P-70 Introduction
P-70.1 General Methodology
P-70.2 Seniority of Radicals and Ions
P-70.3 Name Formation
Suffixes, prefixes, and endings for radicals and ions in substitutive
P-70.3.1
nomenclature
P-70.3.2 Basic multiplying prefixes
P-70.3.3 Order of citing suffixes and endings
P-70.4 General Rules for the Selection of Preferred Names
P-71 Radicals
P-71.1 General Methodology
P-71.2 Radicals Derived from Parent Hydrides
P-71.2.1 Monovalent radicals
P-71.2.2 Divalent and trivalent radicals
P-71.2.3 Multiple radical centers (polyradicals)
Acyclic radicals derived by the removal of one or more hydrogen
P-71.2.4
atoms from nonterminal chain positions
P-71.2.5 The λ-convention
P-71.2.6 ‘Added indicated hydrogen’ for radicals of mancude systems
P-71.3 Radical Centers on Characteristic Groups
P-71.3.1 Acyl radicals
Removal of hydrogen atoms from an amine, imine, or amide
P-71.3.2
characteristic group
P-71.3.3 Polyamine, polyimine and polyamide radicals
Removal of the hydrogen atom of a hydroxy group (or chalcogen
P-71.3.4
analogue) of an acid or hydroxy compound
P-71.4 Assemblies of Parent Radicals
P-71.5 Prefixes Denoting Radicals
P-71.6 Order of Citation and Seniority of Suffixes ‘yl’, ‘ylidene’, and ‘ylidyne’
P-71.7 Choice of Parent Radical
P-72 Anions
P-72.1 General Methodology
P-72.2 Anions Formed by Removal of Hydrons
P-72.2.1 Functional class nomenclature
P-72.2.2 Systematic nomenclature
 P-72.2.2.1 Anions derived from parent hydrides and their derivatives
P-72.2.2.2 Anions derived from characteristic groups
P-72.2.2.2.1 Anions derived from acids
P-72.2.2.2.2 Anions derived from hydroxy compounds
P-72.2.2.2.3 Anions derived from amines and imines
P-72.2.2.2.4 Anions derived from other characteristic groups
P-72.3 Anions Formed by Addition of Hydride Ions
P-72.4 Skeletal Replacement (‘a’) Nomenclature
P-72.5 Multiple Anionic Centers
P-72.5.1 Assemblies of parent anions
P-72.5.2 ‘Ide’ and ‘uide’ centers in the same parent hydride
P-72.5.3 Anionic characteristic groups on anionic parent hydrides
P-72.6 Anionic Centers in Both Parent Compounds and Substituent Groups
P-72.6.1 Prefixes for anionic centers derived from acid characteristic groups
P-72.6.2 Prefixes for anionic chalcogens
P-72.6.3 Systematically formed prefixes that include anionic center(s)
P-72.7 Choice of an Anionic Parent Structure
P-72.8 The Suffixes ‘ide’ and ‘uide’ and the λ-Convention
The suffix ‘uide’ is preferred to the suffix ‘ide’ with a parent hydride
P-72.8.1
named by the λ-convention
The suffix ‘ide’ is preferred to the suffix ‘uide’ involved with the λ-
P-72.8.2
convention
P-73 Cations
P-73.0 Introduction
Cationic Compounds with Cationic Centers Derived Formally by the
P-73.1
Addition of Hydrons
P-73.1.1 Cationic centers in parent hydrides
P-73.1.2 Cationic centers on characteristic groups
Cationic compounds derived from neutral compounds expressed by
P-73.1.2.1
suffixes
P-73.1.2.2 Uronium ions and chalcogen analogues
Cationic Compounds with Cationic Centers Derived Formally by the
P-73.2
Removal of Hydride Ions
P-73.2.1 Functional class names
P-73.2.2 Cationic centers in parent hydrides
P-73.2.2.1 Cationic centers in parent hydrides
P-73.2.2.2 ‘Added indicated hydrogen’
P-73.2.2.3 Diazonium ions
P-73.2.3 Cationic centers on characteristic groups
P-73.3 The λ-Convention with the Suffix ‘ylium’
P-73.3.1 Application of the λ-convention with the suffix ‘ylium’
P-73.3.2 Retained names
P-73.4 Skeletal Replacement (‘a’) Nomenclature for Cations
 P-73.5 Cationic Compounds with Multiple Cationic Centers
P-73.5.1 Assemblies of parent cations
P-73.5.2 ‘Ium’ and ‘ylium’ centers in the same parent hydride
P-73.5.3 Cationic characteristic groups on parent cations
P-73.6 Cationic Prefix Names
P-73.7 Choice of a Parent Structure
P-73.8 The Suffixes ‘ium’ vs. ‘ylium’ and the λ-convention
The suffix ‘-ylium’ is preferred to the suffix ‘-ium’ with a parent
P-73.8.1
hydride modified by the λ-convention
The suffix ‘ium’ is preferred to the suffix ‘ylium’ with a parent hydride
P-73.8.2
modified by the λ-convention
P-74 Zwitterions
P-74.0 Introduction
Zwitterionic Parent Structures having the Anionic and Cationic centers
P-74.1 on the same Parent Compound Including Ionic Centers on Characteristic
Groups Expressible as Suffixes.
P-74.1.1 Ionic centers in the same parent structure
Zwitterionic compounds with at least one ionic center on a
P-74.1.2
characteristic group
P-74.1.3 Anionic and cationic centers on different parent structures
P-74.2 Dipolar Ions
P-74.2.1 1,2-Dipolar compounds
P-74.2.1.1 ‘Ylides’
P-74.2.1.2 Amine oxides, imine oxides, and their chalcogen analogues
P-74.2.1.3 Amine imides
P-74.2.1.4 Phosphine oxides and chalcogen analogues
P-74.2.1.5 Phosphine imides
P-74.2.2 1,3-Dipolar compounds
P-74.2.2.1 Allyl type compounds with delocalized general structure
The propargyl (propynyl) type including compounds with canonical
P-74.2.2.2
resonance forms
The carbene type including compounds having with canonical
P-74.2.2.3
resonance forms
P-74.2.3 Dipolar substituent groups
P-75 Radical Ions
P-75.1 Radical Ions Formed by the Addition or Removal of of Electrons
P-75.2 Radical Ions Derived from Parent Hydrides
P-75.2.1 Examples of radical anions
P-75.2.2 Examples of radical cations
P-75.2.3 Examples of zwitterionic radical ions
P-75.2.4 ‘Added indicated hydrogen’
P-75.3 Radical Ions on Characteristic Groups
P-75.3.1 Radical ions on ionic suffix groups
P-75.3.2 Radical ions other than those named by using ionic suffix groups
 P-75.4 Ionic and Radical Centers in Different Parent Structures
P-76 Delocalized Radicals and Ions
Delocalization in Names Involving One Radical or Ionic Center in an
P-76.1 Otherwise Conjugated Double Bonds Structure is Denoted by the
Appropriate Suffix without Locants
P-77 Salts
P-77.1 Preferred Names for Salts of Organic Bases
P-77.1.1 Preferred IUPAC names for salts of organic bases are binary names
Substitutive nomenclature is used to derive preferred IUPAC names
P-77.1.2
for monosalts of di- or polyamines
Traditional methods of naming salts of organic base when P-77.1.2
P-77.1.3
cannot be applied
Salts Derived from Alcohols (including Phenols), Peroxols, and their
P-77.2
Chalcogen Analogues
Preferred IUPAC names are binary names formed by citing the name
P-77.2.1
of the cation followed by that of the anion
Substitutive nomenclature is used to derive IUPAC preferred names
P-77.2.2
for monosalts of polyhydroxy compounds
P-77.3 Salts Derived from Organic Acids
Preferred IUPAC names are binary names formed by citing the name
P-77.3.1
of the cation followed by that of the anion
Substitutive nomenclature is used to derive preferred IUPAC names
P-77.3.2
for acid salts of polybasic organic acids

P-8 ISOTOPICALLY MODIFIED COMPOUNDS

P-80 Introduction
P-81 Symbols and Definitions
P-81.1 Nuclide Symbols
P-81.2 Atomic Symbols
P-81.3 Names for Hydrogen Atoms and Ions
P-81.4 Isotopically Unmodified Compounds
P-81.5 Isotopically Modified Compounds
P-82 Isotopically Substituted Compounds
P-82.0 Introduction
P-82.1 Formulas
P-82.2 Names
P-82.2.1 Isotopically substituted compounds
P-82.2.2 Isotopically modified compounds
P-82.2.3 Addition of hydro prefixes
P-82.2.4 Location of isotopic descriptor in a two or more word name
P-82.2.5 Location of isotopic descriptor in a one word name
P-82.3 Order of Nuclide Symbols
P-82.3.1 When isotopes of different elements are present as nuclides
P-82.3.2 When several isotopes of the same element are present as nuclides
 P-82.4 Stereoisomeric Isotopically Substituted Compounds
P-82.4.1 When stereoisomerism results from isotopic substitution
P-82.4.2 Isotopically substituted stereoisomers
P-82.5 Numbering
P-82.5.1 Numbering in relation to the unmodified compound
Priority between isotopically substituted and unmodified atoms or
P-82.5.2
groups
P-82.6 Locants
P-82.6.1 Omission of locants
P-82.6.2 Letter and/or numeral locants
P-82.6.3 Location of nuclides on positions not normally denoted by locants
Italicized nuclide symbols and/or italic capital letters to distinguish
P-82.6.4
between different nuclides of the same element
P-83 Isotopically Labeled Compounds
P-83.1 Specifically Labeled Compounds
P-83.1.1 Structures of specifically labeled compounds
P-83.1.2 Names of specifically labeled compounds
P-83.2 Selectively Labeled Compounds
P-83.2.1 Structures of selectively labeled compounds
P-83.2.2 Names of selectively labeled compounds
P-83.3 Nonselectively Labeled Compounds
P-83.3.1 Nonselectively labeled compounds
P-83.3.2 Structures
P-83.3.3 Names
P-83.4 Isotopically Deficient Compounds
P-83.4.1 Isotopically deficient compounds
P-83.4.2 Structures
P-83.4.3 Names
P-83.5 General and Uniform Labeling
Selectively labeled compound, all positions labeled, not necessarily
P-83.5.1
evenly; the symbol ‘G’
Selectively labeled compound, all positions uniformly labeled; the
P-83.5.2
symbol ‘U’
P-83.5.3 Selectively labeled compound. uniformly labelled at specified positions
Comparative Examples of Formulas and Names of Isotopically
P-84
Modified Compounds

P-9 SPECIFICATION OF CONFIGURATION AND CONFORMATION

P-90 Introduction
P-91 Stereoisomer Graphical Representation and Naming
P-91.1 Stereoisomer Graphical Representation
P-91.2 Stereodescriptors
 P-91.2.1 Recommended stereodescriptors
P-91.2.2 Omission of stereodescriptors
P-91.3 Naming of Stereoisomer
P-92 CIP Priority and Sequence Rules
P-92.1 The Cahn-Ingold-Prelog (CIP) System: General Methodology
P-92.1.1 Stereogenic units
P-92.1.2 Rules for the assignment of configuration
P-92.1.3 The Sequence Rules
P-92.1.4 Hierarchical digraphs
P-92.1.4.1 Acyclic molecules
P-92.1.4.2 Double and triple bonds
P-92.1.4.3 Saturated rings and ring systems
P-92.1.4.4 Mancude rings and ring systems
P-92.1.5 Exploration of a hierarchical digraph
P-92.1.6 Ligand ranking: application of the five Sequence Rules
P-92.2 Sequence Rule 1
Sequence subrule 1a: Ligands are arranged in order of decreasing
P-92.2.1
atomic number
P-92.2.1.1 Saturated compounds
P-92.2.1.2 Double and triple bonds
P-92.2.1.3 Saturated rings and ring systems
P-92.2.2 Sequence Subrule 1b: Priority due to duplicate atoms
Sequence Rule 2: Higher atomic mass number precedes lower atomic
P-92.3
mass number
P-92.4 Sequence Rule 3
P-92.4.1 ‘seqcis’ = (‘Z’) and ‘seqtrans’ = (‘E’)
Sequence Rule 3: ‘seqcis’ (‘Z’) precedes ‘seqtrans’ (‘E’) and this order
P-92.4.2
precedes nonstereogenic double bonds
P-92.5 Sequence Rule 4
Sequence Rule 4a: Chiral stereogenic units precede pseudoasymmetric
P-92.5.1
and these precede nonstereogenic units
Sequence Rule 4b: Like descriptor pairs have priority over unlike
P-92.5.2
descriptor pairs
P-92.5.3 Sequence rule 4c: ‘r’ precedes ‘s’
Sequence Rule 5: ‘R’ precedes ‘S’, ‘M’ precedes ‘P’, and ‘seqCis’
P-92.6
precedes ‘seqTrans’
P-93 Configuration Specification
P-93.0 Introduction
P-93.1 General Aspects of Configuration Specification
P-93.1.1 Absolute configuration
P-93.1.2 Relative configuration
P-93.1.3 Racemates
P-93.1.4 The descriptor ‘ambo’
P-93.2 Tetrahedral Configuration of Atoms other than Carbon
P-93.2.0 Introduction
P-93.2.1 General methodogy
P-93.2.2 Azanium (ammonium) and phosphanium (phosphonium) salts
P-93.2.3 Amine oxides and phosphane oxides
P-93.2.4 Phosphates, phosphonates, and related compounds
P-93.2.5 Sulfates, sulfonates, and related compounds
P-93.2.6 Compounds of Group 14 (other than carbon compounds)
P-93.3 Nontetrahedral Configuration
P-93.3.1 General methodology
P-93.3.2 Polyhedral symbols
P-93.3.3 Configuration index and priority number
P-93.3.3.1 General methodology
P-93.3.3.2 Trigonal pyramid
P-93.3.3.3 T-shape systems
P-93.3.3.4 See-saw systems
P-93.3.3.5 Trigonal bipyramid
P-93.3.3.6 Square pyramid
P-93.3.3.7 Octahedron
P-93.3.4 Chirality symbols
P-93.3.4.1 The chirality symbols ‘R/S’
P-93.3.4.2 The chirality symbols ‘A’ and ‘C’
P-93.4 Configuration Specification of Acyclic Organic Compounds
P-93.4.1 Specification of stereogenic centers
P-93.4.2 Specification of configuration for double bonds
P-93.5 Configuration Specification of Cyclic Organic Compounds
P-93.5.0 Introduction
P-93.5.1 Monocyclic compounds
Specification of stereogenic centers: stereodescriptors ‘R’, ‘S’, ‘r’,
P-93.5.1.1
and ‘s’
P-93.5.1.2 Relative configuration: stereodescriptors ‘cis’ and ‘trans’
P-93.5.1.3 Relative configuration: stereodescriptors ‘r’, ‘c’, and ‘t’
P-93.5.1.4 Unsaturated alicyclic compounds
P-93.5.2 von Baeyer compounds
P-93.5.2.1 Specification of stereogenic centers by CIP stereodescriptors
P-93.5.2.2 Relative configuration (‘endo’, ‘exo’, ‘syn’, ‘anti’, ‘cis’, ‘trans’)
P-93.5.2.3 Specification of double bonds
P-93.5.3 Spiro compounds
Specification of stereogenic spiro atoms of the type ‘Xabcd’, here ‘a’
P-93.5.3.1
> ‘b’ > ‘c’ > ‘d’
Specification of stereogenic spiro atoms of the type ‘Xabab’, where
P-93.5.3.2
‘a’ > ‘b’
P-93.5.3.3 Specification of double bonds
 P-93.5.3.4 Specification of nontetrahedral stereogenic centers
P-93.5.3.5 Axial chirality of spiro compounds
P-93.5.4 Fused and bridged fused compounds
P-93.5.4.1 Specification of configuration by CIP stereodescriptors
P-93.5.4.2 The descriptors ‘cisoid’ and ‘transoid’
P-93.5.5 Cyclophanes
P-93.5.5.1 Specification of stereogenic planes
P-93.5.5.2 Specification of chirality centers
P-93.5.5.3 Specification of double bonds
P-93.5.6 Fullerenes
P-93.5.6.1 Definitions and general methodology
P-93.5.6.2 Type 1. Inherently chiral parent fullerenes
Type 2. Substituted fullerenes inherently chiral because of their
P-93.5.6.3
substitution pattern
Type 3. Substituted fullerenes noninherently chiral because of their
P-93.5.6.4
substitution pattern
P-93.5.6.5 Type 4. Chirality due to chiral substituents
P-93.5.6.6 Superimposition of stereogenic elements in a fullerene molecule
P-93.5.7 Ring assemblies
P-93.5.7.1 Specification of stereogenic axes
P-93.5.7.2 Specification of stereogenic centers
P-93.5.7.3 Specification of double bonds in unsaturated rings and ring systems
P-93.6 Compounds Composed of Rings and Chains
P-94 Conformation and Conformational Stereodescriptors
P-94.1 Definition
P-94.2 Torsion Angle
P-94.2.1 Torsion angle ‘X-A-B-Y’
P-94.2.2 If ‘A’ and ‘B’ in ‘X-A-B-Y’ are trigonal centers, a lone pair of electrons
P-94.3 Specific Stereodescriptors
P-94.3.1 Eclipsed, staggered and gauche (or skew) conformations
P-94.3.2 Stereodescriptors for denoting the conformations of alicyclic rings

P-10 PARENT STRUCTURES FOR NATURAL PRODUCTS

AND RELATED COMPOUNDS
P-100 Introduction
Nomenclature for Natural Products Based on Parent Hydrides
P-101 (Alkaloids, Steroids, Terpenes, Carotenes, Corrinoids, Tetrapyrroles,
and Similar Compounds)
P-101.1 Biologically Based Trivial Names
P-101.1.1 Trivial name of a compound isolated from a natural source
P-101.1.2 The ending ‘une’ or ‘iune’
Semisystematic Nomenclature for Natural Products (Stereoparent
P-101.2
Hydrides)
P-101.2.0 Introduction
 P-101.2.1 General guidelines for choosing a parent structure
P-101.2.2 Structural features allowed for parent structures
P-101.2.3 Numbering of parent structures
P-101.2.4 Identification of individual rings
P-101.2.5 Atomic connector, terminal segment and bond connector
P-101.2.6 Stereochemical configuration of parent structures
P-101.2.7 Semisystematic names of recommended fundamental parent structures
P-101.3 Skeletal Modifications of Parent Structures
P-101.3.0 Introduction
P-101.3.1 Removal of skeletal atoms without affecting the number of rings
P-101.3.2 Addition of skeletal atoms without affecting the number of rings
P-101.3.3 Bond formation
P-101.3.4 Bond cleavage
P-101.3.5 Bond migration
P-101.3.6 Removal of a terminal ring
P-101.3.7 Combination of the prefixes ‘cyclo’, ‘seco’, ‘apo’, ‘homo’, and ‘nor’
P-101.4 Replacement of Skeletal Atoms
P-101.4.1 General methodology
P-101.4.2 Skeletal replacement of carbon atoms by heteroatoms
P-101.4.3 Skeletal replacement of heteroatoms by carbon atoms
P-101.4.4 Skeketal replacement of heteroatoms by other heteroatoms
P-101.4.5 Indicated hydrogen
P-101.5 Addition of Rings and Ring Systems
P-101.5.1 Mancude rings and ring systems incorporated by fusion nomenclature
P-101.5.2 Rings and ring systems incorporated by bridged fused ring nomenclature
P-101.5.3 Rings and ring systems incorporated by spiro nomenclature
P-101.6 Modification of the Degree of Hydrogenation of Parent Structures
P-101.6.1 By changing ‘an’ or ‘ane’ to ‘ene’ or ‘yne’
P-101.6.2 The descriptors ‘E’ and ‘Z’
P-101.6.3 The prefix ‘all’ is used in front of stereodescriptors
P-101.6.4 Double bonds in a parent structure modified by the prefix ‘hydro’
Carbocyclic or heterocyclic ring components fused to a parent structure
P-101.6.5
saturated using ‘hydro’ prefixes
P-101.6.6 Additional unsaturation in a parent structure by the prefix ‘dehydro’
Rearrangement of double bonds by a combination of ‘hydro’ and
P-101.6.7
‘dehydro’ prefixes
P-101.7 Derivatives of Parent Structures
The suffixes and prefixes of organic nomenclature and the
P-101.7.1
stereodescriptors α, β, and ξ
P-101.7.2 Modifications of principal characteristic groups
Substituent groups derived from parent structures by the suffixes ‘yl’,
P-101.7.3
‘ylidene’, or ‘ylidyne’
P-101.7.4 Addition of rings denoting functional groups
 P-101.7.5 The prefix ‘de’ (not ‘des’), followed by the name of a group or atom
P-101.8 Further Aspects of Configurational Specification
P-101.8.1 Inversion of configuration
P-101.8.2 Racemates
P-101.8.3 Relative configuration
The stereodescriptors ‘R’ and ‘S’ for absolute configuration of an achiral
P-101.8.4
parent structure and after ring opening
P-102 Carbohydrate Nomenclature
P-102.1 Definitions
P-102.1.1 Carbohydrates
P-102.1.2 Monosaccharides
P-102.1.3 Oligosaccharides
P-102.1.4 Polysaccharides
P-102.2 Parent Monosaccharides
P-102.2.1 Parent aldoses and ketoses with up to six carbon atoms
P-102.2.2 Numbering parent structures
P-102.3 Configurational Symbolism
P-102.3.1 The Fischer projection of the acyclic form
P-102.3.2 The stereodescriptors ‘D’ and ‘L’
P-102.3.3 The configurational atom
P-102.3.4 Cyclic forms of monosaccharides
P-102.3.5 Conformation of monosaccharides
P-102.3.6 The Mills depiction
P-102.3.7 Stereodescriptors for denoting racemates and uncertain configurations
P-102.4 Choice of a Parent Structure
P-102.5 Monosaccharides: Aldoses and Ketoses; Deoxy and Amino Sugars
P-102.5.1 Aldoses
P-102.5.2 Ketoses
P-102.5.3 Deoxy sugars
P-102.5.4 Amino sugars
P-102.5.5 Thio sugars
P-102.5.6 Substituted monosaccharides
P-102.5.6.1 O-Substitution
P-102.5.6.2 Glycosides
P-102.5.6.3 C-Substitution
P-102.5.6.4 N-Substitution
P-102.5.6.5 Alditols
P-102.5.6.6 Monosaccharide carboxylic acids
P-102.5.6.7 Anhydrides
P-102.6 Monosaccharides and Derivatives as Substituent Groups
P-102.6.1 Glycosyl groups
P-102.6.2 Substituent groups other than glycosyl groups
 P-102.7 Disaccharides and Oligosaccharides
P-102.7.1 Disaccharides
P-102.7.2 Oligosaccharides
P-103 Amino Acids and Peptides
P-103.0 Introduction
P-103.1 Names, Numbering and Configuration Specification of Amino Acids
P-103.1.1 Retained and systematic names
P-103.1.1.1 Retained names of the ‘common’ amino acids
P-103.1.1.2 Retained names of ‘less common’ amino acids
P-103.1.1.3 Systematic substitutive names
P-103.1.2 Numbering of α-amino carboxylic acids
P-103.1.3 Configuration of α-amino carboxylic acids
P-103.2 Derivatives of Amino Acids
P-103.2.1 System for denoting locants
P-103.2.2 Names of substituent groups
P-103.2.3 Derivatives formed by substitution
P-103.2.4 Ionization of characteristic groups
P-103.2.5 Acyl groups
P-103.2.6 Esters
P-103.2.7 Amides and other nitrogenous derivatives
P-103.2.8 Alcohol, aldehydes, ketones and nitriles
P-103.3 Nomenclature of Peptides
P-103.3.1 Definitions
P-103.3.2 Names of peptides
P-103.3.3 Symbols of peptides
P-103.3.4 Indication of configuration in peptides
P-103.3.5 Modification of named peptides
P-103.3.5.1 Replacement of residues
P-103.3.5.2 Extension of the peptide chain
P-103.3.5.3 Insertion of residues
P-103.3.5.4 Removal of residues
P-103.3.6 Cyclic peptides
P-104 Cyclitols
P-104.0 Introduction
P-104.1 Definitions
P-104.2 Name Construction
P-104.2.1 Stereoisomeric inositols
P-104.2.2 Cyclitols other than inositols
P-104.2.3 Numbering on cyclitols
P-104.3 Derivatives of Cyclitols
P-104.3.1 Derivatives of inositols
P-104.3.2 Derivatives of cyclitols other than inositols
 P-105 Nucleosides
P-105.0 Introduction
P-105.1 Retained Names of Nucleosides
P-105.2 Substitution on Nucleosides
P-105.2.1 Substitution of nucleosides
P-105.2.2 Nomenclature when a higher priority characteristic group is present
P-106 Nucleotides
P-106.0 Introduction
P-106.1 Retained Names
P-106.2 Nucleoside Diphosphates and Triphosphates
P-106.3 Derivatives of Nucleotides
P-106.3.1 Nucleotides having retained names
P-106.3.2 Analogues of nucleoside di- and polyphosphates
P-106.3.3 Nomenclature when a higher priority characteristic group is present
P-106.3.4 Oligonucleotides
P-106.3.5 Nucleotides with phosphorothioic acid
P-107 Lipids
P-107.0 Introduction
P-107.1 Definitions
P-107.2 Glycerides
P-107.3 Phosphatidic Acids
P-107.3.1 Phosphatidic acids
P-107.3.2 Configuration of phosphatidic acids
P-107.3.3 Phosphatidylserines
P-107.3.4 Phosphatidylcholines
P-107.3.5 Phosphatidylethanolamine
P-107.3.6 Phosphatidylinositols
P-107.4 Glycolipids
P-107.4.1 Definitions
P-107.4.2 Glycoglycerolipids
P-107.4.3 Glycosphingolipids
References
Seniority list of elements and ‘a’ terms used in skeletal replacement (‘a’)
Appendix 1
nomenclature
Appendix 2 Detachable Prefixes
Appendix 3 Structures for Alkaloids, Steroids, Terpenoids, etc.