Literature of Organic Chemistry FINDING WHAT'S KNOWNINTRODUCTION PRU Uae ey Ib ned tobe eeportd o sient round the world. Publhing heres oflaboratory studies allows sce euewhere to have acest the details 0 ‘hey can stay informed on esearch progres intel fds, verify the findings, and ‘them as aspringhoard for ture work on nev ea. nthe organics lab te dnt want fo rewen the whed swe need to know whats been done befor. Ta {Go this we need 1 Know how to earch nthe vast historical records of al organic ‘hemi research anditcan be ike finding ned in ahaystack Here you eam bout ome ofthe search oo and eta bi of experience using them. R rls ofthe scene eld you may be staying, discoveries made in the “Thee are many type of ceristey erature, bat they ate generally categorized as primary secondary sources, We ok fst the primary sources which are writ tenby the people wh actualy perform the reach Tourals ootin ew work. Thee ae thousands of journals in ll els. About 50-100 of them pertain to orga chestry. Journals contain ates also called {ul paper) aa commaniatons,Commecations (also called letter) are bri re ‘ports intended for rap pulicaion, and generally contin preliminary data that fan be republished in «more compete form late Data in articles or full popes ‘annot be republished. Thorgani chest. nativ English speaker aeluckybecuse the most import sant journals are published or are ransated nto Engh worldwide. Nevertheless itean bea great advantage to ead German, because Germany was the chemistry leader prot to World Wat I and may ofthe most important onganic chess ofthat er published their esac in German. Arties in Russian, French, nd Japanese are common aswel At st users, iis aot hard find peopl with seme scientific vocabulary who can rsd these languages, abd ofen they are willing fo trast sn atc nexenange ora batch of cooks orca beverage 1h few ofthe most niportant journals that push organic chemist research areas follows: Angew Chemie International Eton Ballin of he Chemical Society ofapan Chemical Commanicaions europe Journal of Organic Chemistry (rey stu ibis Anmalen der Chemie) our of be American Chemical Society Journal of Medicinal Chemistry Jounal of Orgone Chemiry Journal of Ogunametlc Chemistry Nature ‘Orpoic and Biomolecular Chemistry formes Journal fhe Chemical Sac Perkin Transaction 1) Organic Lets Me CHAPTERD | Utertzeof rca chenstry Selence ‘Tetrahedron Letters In this in the standardized journal abrevitions are inde Un bod, witha period flwingeach abbreviated ern in the cation) Am her Soe) Somc of {he jour cvera range of enti else. Nature and Scene) sme aespeciic ‘shes (eg Chem. Commun. of Am. Chet. So), and oters are ever moze {pesto the dcpin of organi chemistry Bu. Ory Che or. Ory Chem). ‘Chemists can apy fr pens for ner compounds oa new method for mak ‘ng «known compound (maging 20-30% of al patents ae cherie patents) ‘hare willbe comsidrabe infomation athe polly valle documentation that, accompanies the ptt Industry scents may patent much of heir work eout er publishing some important discovers wil only be Found by searching in the patent ierstre, Unfortunately, patents are not ery any ord, beaut hey ae writen in legal termisology that sometimes seems ik a diferent language ‘Als, eventhough patents are supposed to provide a fll islosre, they may con cal important information to maintain competitine business advantage Pres seo mela} (9.28 | Early Print Databases ‘xensve effort has gone nt sorting key cements fog chemistry primary ter ture sources ino searchable form. One the int mportant ol fr hs was the Bel eins Handbuch der Organichen Chemie which Deanne 180s Asitwas regularly ips, becate an indapesabe et of hick printed volume led with ysl stator rani compounds aswell rlabie procedresor tht prepaation. Ik ‘ns however writen in German snd wort ina somewhat exter faion, dhe Unted Sates, Chemical Abstracts emerged a8 an alternative way sort. through the primary Iersture. Chemical Abracts provides short summaries, ‘alled abstracts, of may primary soures of information ands thus extremely ase Talfor"huming down” information, Its pesodially published by the Chesca ‘Abstracts Service (CAS), branch of the American Chemical Solty, and became ‘hemo comprehensive database forall reef chemitry ‘To hep track of everything published abbut each unique orpanke compound, the Chemical Abstracts Service (CAS) assigns a CAS etry number o evry com: ound when ti first reprted in the Ierature. This CAS uber such Uke 8 Social searty amber Thus, while a compound may have diferent names in i feet languages it has only one CAS retry nue. There are over 70 milion ‘hemial substances with seit amber, nd abot 15.00 are added cach dy. Other serch oosand databases use the CAS regatry number aan indexing eh this allows chemists to cross-reference compounds aros diferent platforms and ensure preci searches for information, 9.28 | Modern Electronic Databases ‘The data found nthe piste form of Bestlnand Chemical Abstactshave been dig- tz, and have been walble in various electronic format fr about 30-40 years, ith se interac gradually tansforningalog wih updated database software. Inthe ate 1990s, some very ter friendly online interfaces merged 1o ake ava ‘ipso the explosion a terme capabilities. 92 Secondary SocSCIFINDER (hitps:/scifinder.cas.org) SciPineris the cuvent online interac tothe Cham Abstracts database which Incaesabteactsof papers from thousinds of ourmls dating fom the 18005 to the presen tis updated daly as nee papers areas Rescarch universities gen erally have subscription acess to this database avlble ia thee Slences brary seebits Other institatons may have aces aswel rd you sould check wth your Testuctor for Sifinder aces detail that re specfito your location. Access may Leese the eho have iar pepe ‘Once in Sines you wil sce a sidebar tet vith choices of how to serch for abt All Substances, Reactions, References, ana Supplies. Each ofthese x jpnds toalow a ange of dleent serch types e gure 9.3) The fllowing tea Few example ofthe variety of way o sear fo abstats on SciFinder 1. Author name; Within the Reference search tol you can oak up an author, suchas Robert Wooded (gure). Research ope You ca look up Keywords such as catalysis. Multiple [eynouds en be entered to focus the search on anarower tpl, such a8 1 chromatography terpenes in ctus pel A cick "Search the various combinations of thes tems wll appesrong with tats on how my references there are for ech comb ion ofterms For example, youcan select lists that inde refrence with all theterms coy associated oss with some ofthe terms fund any rere inthe reference. Aer you elect ait he abstract foreach fren that ist wl pps shown n Figure9.2.Soaetimes the ist of eee {ser lng a sf tal toro the st such s Fie by and Bxlude arefound ina debr athe For example, cleking oa ‘Document Type Review” could shorten the list fom 28 9105 references. These tools a ‘a CHAPTERS. | erate of Ogpnlechamsty ES a SO fp nemo i rma trp ree sls narrow the search eats to ected aut, specific yar of publica to certain wives adres fi authors, ther ers Each abstract in SciFinder proves extensive information about what canbe fund inthe reference, ncluing the flowing: + tent ofthe paper 1 suor names and addreses ‘+ name ofthe jourmal andthe eas volume, and page number 1 languagein which the paper wasriten| {+ ashortsummary describing the ey points of the paper Clicking onthe ite gives deta nformation to explore re deeply. “hiss how you can find the SiFncer abstract numer (AN) that you se tocdletheabsract, (Chemical utance: You can ok up cemialby tsname eg. “ewdaherane”), CAS gsry number (41082: o¢ formula CH). Alert, SiFinder fers plugin drawing apSeations igure 93) hat willow the strctore tobe ecognied and ened for searching. Once astucture isda. itcan bused to sear for chemical substances oF for ection in hich thestrctureisa component ab eactant or pda. Jornal: You ca vew abstract forthe ails biced i particular joureal an yar ‘he search types noted her oferaninteductory starting pint. Te best way to Hearn more isto explore the options s you earch, 2 Seendar/souces 9REAXYS (https//wrm.reaxys.com) ‘Ted ound in sn may now be assess using Rear software Varios search formats are pose, bt the moat powerful te strctre searching, Whi this arto] may notes comprehensie a seuching with einer, compere earch sofen more han you need. Chemical and pasa popes and syathese procedures fo several milion compounds maybe found with Reays and the dat are ror in a convenient format with eas and eanyovead sutures, WEB OF SCIENCE (https/clarivate.com/webofsciencegroup ‘solutions/eb-of scence) ‘Wb of Slenceinles dat from a resource called Science Citation Index (SCI) Searching by keyword autor author’ addres, and he ike are very easy with Web sf Seine, but ulikeSiFinder or Ressy, Wb of Since dove nal serchee based onthe structures or physical properties of compounds I provides abstracts and bibliographic datafor allie important publications inthe phys sence. The ‘atin Web of Scienccor Science Caton Inde arin by the ferences cite, 39 ‘hat once you ind an ay paper about a key discovery, you can then inal f the Inter aries hatte that ear paper Assuming dhe more ecent authors propel ‘ted the eae paper ths can bea very valuable way tofllow a esearch area fom Isoigns ight op othe eating edge SeiFinder lo allows cation Searchlng. ‘ciFider, Resxys, and Web of Slece all have ative inks to the papers they tefeence,s0 you can cick nd download the original artl, slongas our iary has subleripton to tar esouce 9.2¢ | Compendia of Tables and Information ‘Avalble bh online cd in petted format, some useflexamplesf these evources Incade the folowing 1. Combined Choncal Dieonary (CCD) (psi chemnetbasecom) ‘With CCD, you cn search ona chemical name o draw structure and do ‘search ont, CCD ilo a quick way to obtain the CAS rity numer for chemical :ompound, universal entir which may make searches on other datbises ike SDBS (blow) ease. AIST Special tabuse for Organic Compounds SDBS) htpldbs ait “gj SDBS isa es hased source of NMR IR, and mas spect das I ‘ful for making comparisons wih the pects tat ou wl allen this “Handbook of emir and Pose (pio chemetbae com). This ‘volume, often st ale the CRC fulf information including the ble ‘on the“ Physic Constants of Organic Compounds” Mos ibrries have ‘opie f this lable for contain, ‘The Merck nde bp oper: nds) The Marck nde is god source of nformtion about chemicals of medial importance, Physical ‘constants ofthe compounds, and reference to papers abot thee sys ‘ne povided ang with information abou the clinical laboratory ws. Haubookof Pe Chemicals htpsww sigmaach com). The Alich hundbook rally chemical sales catalog, bt contains physical con stants onal de chemicals they sal Most organic abs havea couple ofthe ‘volumes ovale I nts avaiable online 150 CHAPTERS. | LteauVe Forge chamisry (9.20 Reviews ‘hes artis provide intensive surveys faternarow lds of resach, review prides an overview of sj. 50 an hea god starting pnt nan anes af teach especly wen you lc ie to ea al of he piary Irate Be ae, weve, that you are geting th author or authors) view fsb, nd hey may sotbe ling you everything you realy watt katt Jourealsthat nude reve Accounts of Chemie! Remrch Angenandte Chem bnteaaional Eton x Baglsh Chemical Reve! Cenc Scie Reviews 9.2¢ | Popular Press woe Important perk hat cess ead ate Discover Mapicine Sei American Choc and Empncering News weckychemistry news rm the American Chemical Society) 9.2¢ | Serial Publications “These resources at lik reviews but are published iegularly ad are harboun a Bene iodate Advance in Ongoic Chemistry Advances in Photochemistry Advances in Proein Chemistry Orpic Spies Progr in Macroeyiie Chemistry | 9.2G | Textbooks and Reference Books ‘These texts range fom sophomore ee to graduate level Just afew examples of seme consmonly asd advanced bok ar ite here Some of the reference books Ise ben converted it online database format. (Carey EAs Sundberg, Advanced Orgone Chemistry Se Pats Aan B Springs: New Yok. 2007 Sith M.B Maré Advanced Onc Chom: Reactions Mechonons, and Src, 7s ed: Wie: New York, 2013. lect Encylopedia of Reagents for Organi Syuheis Onin] Wiley bps ‘onlnelbaryieycom/de/book/10.102/047084289X (cee Api 2022) Larock, RC. Camprhonsine Organic Transformation, Sri es Wiey Nev York, oie Lowry THs Richardson, K.S. Mecano and Thon in Organic Chis, Sed; Harper and Row: New York, 1957 ‘Nelo, K. C: Sorensen, EJ. lass in Taal Sythe; VCH: New York, 1996, Secondary Sores‘Nico K, Cs Snyder SA lass Total Spt Is VCH Nee York, 2008, Reich Hf Total Sythe [Onin] psorganicchemisrydst orghanseich esourceslyatheses (acest Apri 2022), Roi Kens Rue eta Ud Matra inthis scion canbe found inthe ACS Guide 0 Scholarly Communica: rion (itpspubsacs.orgfoibook/TOA02Lacagide). An abbrevited companion resoure, ACS Sie Quick Guide (htpspubs.ack. oda 0102Vacsguide ‘HO30), provides easy acces to some ofthe most useful content ‘When ching single work, generally follow one af these two examples + lisknows that he Diels-Alder action provides ast membered rng” 1 isknown tha the Diels-Alder enton peotdes ast membered rng). When cing multiple works, generally follow ane af these two examples: + Recent investigations inlet ainkbetwen temperature and ection Recent investigation (2, 4-9) inate alink betwen temperature and Dire sbliplines may have diereat standard forthe citation indicator. ‘Most chemistry aural se superscript aumerals bat he parenthetical style of ten used in Brochemisry. Your inetractor wel ily express a stye requirement, and you should low that careflly Slay the tle ofthe way biiographi i fertatin provided nthe tation iuelfcan vary; some Journals require inclusive ‘ogination bot sts snd end pages of en arte or chapter and snse quire the frie ile. The examples presented in thi chapter ae a standard style associated ‘withthe fournal of he American Chm Solty. [9.34 | Citing Books In book citations, authors appear frst, followed bythe book tile in als. single tutor o group of authors may hae writen the whole book, o the book may have teen compiled by an editor with a numb of separate chapters writen by diferent tutors, The author names appear with fray same ast name, lowed by Ss td mid inal, Depending on the stuntio, you may need 16 ete a particule ‘hap, n which cae the chapter author), chapter te, chapter page numbers snd the editor areal sted inthe reference, tation ofa whole books Ware, SG. Ono Symes, the Dicomnstion _Appoacs Wile: New York, 1982 tation ofthis boa Festa GK. Tehnques and Experiments Organic Chemistry: Boag Perpetvs and astainabi, W. W. Norton: Ne York m3, Cation chapter win a book read G.K Ammar Rael Adon to Chiral ydraaones in Tp Current Choisy Radical Sys (Gansue, A each, M, Eds Springs Verlag Bei, 2012 Va 320, p 61-82. 182 CHAPTERS | Uterotreoforgane chemistry { 9.38 | Citing Journal Articles Journal article authors arecltedin the same order ven nthe atc, Tees fo ‘als also appear in italics, For journal, the year appears in bld and he volume number in ales, followed by page numbers, x shown nthe flowing example MacGillry. Rs Rid Ls Ripmeesi, JA. A. Ghent Sae. 200, 122, 17817-7818 (This means yar 200, volume 122, pages 78171 7818) \ 9.3€ | Citing Theses or Dissertations ‘Grubs RH. 1 Cycobutdiene Destin IL Stes of Oonctatetsene on ‘reabonyl Camplees PRD. Disertato, Columbia Univer, New Yr, 166 2230 | Citing Personal Communications imstone, Peiastone University, Bedrock, CT: Personal communion, 1958 ~0.3E | Citing Material from the Internet ‘Usethetile provided onthe west, and fu isunclar whether the ieee tan Internet location, ad the words "Home Page” to clariy. cade the date accessed, trary of Congres Home Peps wo gov (accessed May 222), rmtes A.J. Nov Voodoo X-4 Deming Syl Ogonic Chemin since [204 hipifmwchemcoceterc/etoodon ceed Apel 203 9 | Citing Computer Programs Computer program sepa ced ng the ook ma Deppmcie B: Driessen, A Here. Here, W Klunsinge, Bs Oger Schntt, Spartan (182, 1-46} Waveuncton, Ine: Irvine,CA 20. Pb acc ‘his asignment consi of thee parts “Tble of hema and their properties SciFinder search and one paragraph summary of primary ressarch publication Summary ofa eview/popular atl (oe ge) “5.44 | Creating a Table of Chemicals and Their —""~ Properties ‘Your istracor wil assign alist of 3-5 compounds, smi to the numberof mate sls you would be using in type laboratory eperaent,Use he handbook and sateerweAigomene 55atbsses sted previously inthis chapter to prepare ble of properties af th om pounds ncading baad information. Sina information shouldbe gatberedbetore ‘ach experizent. or each chemical compound, provide 1 Name Formula 5, Formola weight 4 Strstare raw the strotare) | Meling point or bila point (note the pressure sno 760 mm) {6 Physi state trom temperature (gs, slid, Laud, solation in save) Any hazardous indications eg tx, amma, carcinogen. ete) 8. Source, incuding page number An addtional column canbe add for commentst caifyany othe above pons ‘Waring Do nor etal you information from one webtor bok. Use at east to sources namely one web source and one nove source, you discover se ‘nd we source tat useful then you may use tin place ofa none sure. You ‘aya use a source ha ea iste, a ong as yu ce it propery. Some chemical ‘Compounds ppt std mle inesin some resoures, such asin the Arch “lo, These might ot ete same they oul becompoundsof the same name bat ontaning otopc substations (eg datum in pac ofhydrogen asin CD,OD or ead methanol where D sepescts Ho there may be tet eel of py fred bya commercial supple: Us iformation about the material of highest purty ‘uheneer psu, Finally mos prin ours have a formula index o CAS regty ‘uner inex inthe font or back that may be useful when he compounds mane in some uncxpcted Wy. 9.48 Performing a SciFinder Search ‘Use Sande to ook up one folowing chemistry authors based an the eter ‘hat your last mame bess wih ‘YOUR LAST NAME | CHEMISTRY AUTHOR “ ici Be [peti oy time Men i wo 8 Po = el uz "Tw christina White | uertur oforgaiechensey ‘Usethe lowing nea pln for locating an arte expecthistoakea wil: 1. Regster fr Sifinde through your ibary website. Aller eistring, you ‘amuse the webe anywhere. Once you link to Scar you willbe taken toasereen witha vary of search options. Sind deals tthe key word search 50 ou must change the earch “autho fortis par. Search for yoursatho You may search bythe autor stand lst mame, lastname oly st nae an fet nls. For thi asgnmen, er form your serch bab onthe name given above (tile nti as SciFinder wil provid alia of abtacts that match your search, You have been sgn author bated pon your lst name. One proble tha ou eed o coset aeratve ames that coud be usd or instance, some Df Sarah , Reisman paper could ited under. E. Reiman o Sarah Reiman ge hee could be ante pezsn ofthe same oe sila name Find journal tee that deals with some open orgie cert ‘Most tation il iio link to PDF (or HTML) versions ofthe fal ext attic, lic onthe “ull Test” con given with etch entry then, you wl be Aieted oa wes where you can vew/owalod the paper Ifthe article that you woul! He unavailable on Saindr, your be bet willbe toa foncof the irr ansto lp yo act th ara on the rary website Print both the abstract and theirs page of the Journal artic Re prepared tote the ailing the journal article ition format. Include copy of the abstract ana page ofthe paper with you assignment ‘Once yo Find jon artic, provide one pragraph summary ofthe wok Do nasimplyrewelte th abstract Use your own word and use good English with complete sentence. Yor need not analy the paper in deta ecase much ofthe paper my be unfamila-to you. Along with the one paragraph include one or more ‘hemi! states ora eaton souence. The whole of hs (ext plus pcre) sold not be mor than ome page fog or ou wl lose points. You mast ct the ou ral atl, An examples given a the end of his chapter. 9.uc | Preparing a Summary of a Review Article or Popular Journal Article ook through the following review and popular journals, and finda review article to be hard-core chemist, jst chemistry relate. The article you choos should be at east two pages long, you el tall certain about your hoe, el ree wo se {ston Simply tart canning the following journals and magazines wil you fod something interestg, Accountof Chem Resch Jounal of Chemica Education Chemistry and indir (Londen) Discover Magazine Chemisnyn Bri Scenic American (Chemica Engvcring New 94 Leroi Aignerbe longer than one page, and i doesnot aes to inca ites uns you Wish | Print theft pgeof he acti and sare te arte Your summary cannot dos, Atak th ist page your ausiment. Make sue you te te arte prope: yw are unsure aout ay information i your table, cde a question mark or & consent. Your table canbe turned 91" onthe page you wish, andi cam be more than one age long necessary. Note that unis are provided in the alum headings. | | 9.40 | Assignment Examples CcHeMtcaL TABLE j The lloring ble conan al ofthe norton reed fr each compound ih FORMULA | Name FORMULA sTRUCTURE srate_| wazaros | source | comments wieacd WOON Tt cores, 1 Nomporop | fig onaoer oven Packare! gino e5882 mp Sekd Ameo 23. Omer mare paste ses Tal | Petyinyidne “GN N06I6 ON pike Uqad cavesie, & “Tecnica ‘one oat [ nce LL a REVIEW/POPULAR ARTICLE SUMMARY Afr your SciFinder search, you wil ned to prepare a summary ofa primary ‘search publication that yu find Please ollow the general ormat presented inthe Jalowing example Number yor picts schemes also graphs so tat you ean ref to tem easly nthe text Ii ot necessary ogo int exhaustive deal Ty #2 Pckout at est one ete that ys understand and highlight / fe curry | war sr Cty of strychnine by a longest inear sequence of six steps. Sty kalo that hasbeen synthesized by afew diferent chemists inloing ‘ote Laureate RB Woodward In this paper, Martin and C Vanderval describe { yiteasofsrychnine hat ismich sorter than any ofthe prior one. There ar a oun of key steps in ths synthe highlged in Scheme 1. Fst, the authors de ‘eloed away to open the ring of Pyne cation (compound 1) to generate a dene (Goapoand 2 fora Diels-Alder reaction The Die Aler reaction farm cys te hats para pole ing system in compound 3. The alkene poston has noe from ts nly expected cation so that tin conjugation wth the ae bye Te othe lay steps 2 confgt addition fa carbanin tothe beta postion ff the aiphaetasanatred alee 4, foming snother rng Thi reaction ook dvesage of Book cefrangment tht nsf a siicon group toanalkanide on, In oder t make the carbanon. After another sep, the sythess of strychnine was completed. The overall sythent required tal of aie steps—tee tps fr ane rath ofthe synthetic ava, nsx steps inthe main sequence, Most of he other synths of strychnine Gacading Woodward’) have eguired 200 3steps, so this ‘yas big improvement. Sheme I: igure 94 sources: Marts, D. B.C: Vanderwal, C.D. A Syahess of Sryhnine by a Longest near Sequence of Six Steps. Chem, Sl. 2041, 2, 689-65 Web of Skence. htp:larvte com eboiceneegroupeitions Iheb-of scence! aces Api 2022, ‘iterate esnnre