Chemistry for Pharmacy Students

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 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