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Chemistry for Pharmacy Students General, Organic and Natural Product Chemistry Satyajit D. Sarker University ofUlster, Coleraine, Northern Ireland,UK Lutfun Nahar University ofUlster, Coleraine, Northern Ireland,UK Chemistry for Pharmacy Students Chemistry for Pharmacy Students General, Organic and Natural Product Chemistry Satyajit D. Sarker University ofUlster, Coleraine, Northern Ireland,UK Lutfun Nahar University ofUlster, Coleraine, Northern Ireland,UK Copyright#2007 JohnWiley&SonsLtd,TheAtrium,SouthernGate,Chichester, WestSussexPO198SQ,England Telephone(þ44)1243779777 Email(forordersandcustomerserviceenquiries):[email protected] Visit our Home Page on www.wiley.com AllRightsReserved.Nopartofthispublicationmaybereproduced,storedinaretrievalsystemor transmittedinanyformorbyanymeans,electronic,mechanical,photocopying,recording, scanningorotherwise,exceptunderthetermsoftheCopyright,DesignsandPatentsAct1988or underthetermsofalicenceissuedbytheCopyrightLicensingAgencyLtd,90TottenhamCourtRoad, LondonW1T4LP,UK,withoutthepermissioninwritingofthePublisher.RequeststothePublisher shouldbeaddressedtothePermissionsDepartment,JohnWiley&SonsLtd,TheAtrium,Southern Gate,Chichester,WestSussexPO198SQ,England,[email protected],orfaxed to(þ44)1243770620. Designationsusedbycompaniestodistinguishtheirproductsareoftenclaimedastrademarks.All brandnamesandproductnamesusedinthisbookaretradenames,servicemarks,trademarksor registeredtrademarksoftheirrespectiveowners.ThePublisherisnotassociatedwithanyproductor vendormentionedinthisbook. Thispublicationisdesignedtoprovideaccurateandauthoritativeinformationinregardtothe subjectmattercovered.ItissoldontheunderstandingthatthePublisherisnotengagedinrendering professionalservices.Ifprofessionaladviceorotherexpertassistanceisrequired,theservicesofa competentprofessionalshouldbesought. OtherWileyEditorialOffices JohnWiley&SonsInc.,111RiverStreet,Hoboken,NJ07030,USA Jossey-Bass,989MarketStreet,SanFrancisco,CA94103-1741,USA Wiley-VCHVerlagGmbH,Boschstrasse12,D-69469Weinheim,Germany JohnWiley&SonsAustraliaLtd,42McDougallStreet,Milton,Queensland4064,Australia JohnWiley&Sons(Asia)PteLtd,2ClementiLoop#02-01,JinXingDistripark,Singapore129809 JohnWiley&SonsCanadaLtd,6045FreemontBlvd.Mississauga,ONT,L5R4J3,Canada Wileyalsopublishesitsbooksinavarietyofelectronicformats.Somecontentthatappearsinprint maynotbeavailableinelectronicbooks. AnniversaryLogoDesign:RichardJ.Pacifico LibraryofCongressCataloging-in-PublicationData Sarker,SatyajitD. Chemistryforpharmacystudents:general,organic,andnaturalproductchemistry/SatyajitD.Sarker, LutfunNahar. p.;cm. Includesbibliographicalreferences. ISBN978-0-470-01780-7(cloth:alk.paper) 1. Chemistry–Textbooks.I.Nahar,Lutfun,Ph.D.II.Title. [DNLM:1. Chemistry,Pharmaceutical.2. Chemistry.QV744S517c2007] QD31.3.S3772007 540–dc22 2007017895 BritishLibraryCataloguinginPublicationData AcataloguerecordforthisbookisavailablefromtheBritishLibrary ISBN978-0-470-01780-7(HB) 978-0-470-01781-4(PB) Typesetin11/14ptTimesbyThomsonDigital PrintedandboundinGreatBritainbyAntonyRoweLtd.,Chippenham,Wilts Thisbookisprintedonacid-freepaperresponsiblymanufacturedfromsustainableforestry inwhichatleasttwotreesareplantedforeachoneusedforpaperproduction. This book is dedicated to pharmacy students from all over the world Contents Preface ix 1 Introduction 1 1.1 Role ofchemistryinmodernlife 1 1.2 Physicalpropertiesofdrugmolecules 3 2 Atomic structure and bonding 17 2.1 Atoms, elementsandcompounds 17 2.2 Atomic structure:orbitalsandelectronicconfigurations 18 2.3 Chemicalbondingtheories:formationofchemicalbonds 21 2.4 Electronegativity andchemicalbonding 27 2.5 Bondpolarityandintermolecularforces 28 2.6 Significanceofchemicalbondingindrug–receptorinteractions 31 3 Stereochemistry 35 3.1 Stereochemistry: definition 36 3.2 Isomerism 36 3.3 Significanceofstereoisomerism indeterminingdrugactionandtoxicity 53 3.4 Synthesisofchiralmolecules 55 3.5 Separation ofstereoisomers:resolutionofracemicmixtures 56 3.6 Compoundswithstereocentres otherthan carbon 57 3.7 Chiral compoundsthatdonothaveatetrahedralatom withfour different groups 57 4 Organic functional groups 59 4.1 Organicfunctionalgroups:definitionandstructural features 60 4.2 Hydrocarbons 61 4.3 Alkanes,cycloalkanesandtheirderivatives 61 4.4 Alkenesandtheirderivatives 103 4.5 Alkynesand theirderivatives 108 4.6 Aromaticcompoundsand theirderivatives 112 4.7 Heterocycliccompoundsandtheirderivatives 143 4.8 Nucleicacids 170 4.9 Aminoacidsandpeptides 179 4.10 Importanceoffunctionalgroupsindeterminingdrugactionsandtoxicity 184 4.11 Importance offunctionalgroupsindeterminingstabilityofdrugs 188 5 Organic reactions 191 5.1 Types oforganicreaction 191 5.2 Radicalreactions:freeradicalchainreactions 192 5.3 Additionreactions 197 5.4 Elimination reactions:1,2-eliminationorb-elimination 223