mechanism and theory in organic chemistry - t h lowry

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1、MECHANISM-$$.NDTHmw&$*+?%>..,-INORGANIC:t,m--.--CHEMISTRY2IhomasH.Lowry,KathleenSchuelierRichardson,MECHANISMANDTHEORYORGANICCHEMISTRYTHOMASH.LOWRYSmithCollegeandKATHLEENSCHUELLERRICHARDSONTheOhioStateUniversityHARPER&ROW,PUBLISHERSNewYork,Hagerstown,SanFrancisco,LondonToNancyandFrankS

2、ponsoringEditor:JohnA.WoodsSpecialProjectsEditor:CarolJ.DempsterProjectEditor:BrendaGoldbergDesigner:T.R.FunderburkProductionSupervisor:WillC.JomarrbnCompositor:WilliamClowes&SonsLimitedPrinterandBinder:HallidayLithographCorporationArtStudio:VantageArtInc.Copyright01976byThomasH.Lowrya

3、ndKathleenSchuellerRichardsonAllrightsreserved.PrintedintheUnitedStatesofAmerica.Nopartofthisbookmaybeusedorreproducedinanymannerwhatsoeverwithoutwrittenpermissionexceptinthecaseofbriefquotationsembodiedincriticalarticlesandreviews.ForinformationaddressHarper&Row,Publishers,Inc.,10East

4、53rdStreet,NewYork,N.Y.10022.LibraryofCongressCataloginginPublicationDataLowry,ThomasH.Mechanismandtheoryinorganicchemistry.Includesbibliographicalreferencesandindex.1.Chemistry.Physicalorganic.I.Richardson,KathleenSchueller,jointauthor.11.Title.QD476.1A68547'.1'375-43926ISBN0-06-04408

5、2-1CONTENTSPrefaceix1THECOVALENTBOND11.1MODELSOFCHEMICALBONDING1-1.2MOLECULARORBITALS91.3HYBRIDORBITALS201.4DELOCALIZEDPBONDING271.5AROMATICITY28PROBLEMS40Appendix1:HybridOrbitals43Appendix2:MolecularOrbitalTheory502SOMEFUNDAMENTALSOFPHYSICALORGANICCHEMISTRY572.1STEREOCHEMISTRY572.2LIN

6、EARFREE-ENERGYRELATIONSHIPS602.3THERMOCHEMISTRY712.4SOLUTIONS842.5KINETICS902.6INTERPRETATIONOFRATECONSTANTS942.7ISOTOPEEFFECTS105PROBLEMS111viContentsAppendix1:DerivationoftheTransitionStateTheoryExpressionforaRateConstant113Appendix2:TheTransitionStateTheoryofIsotopeEffects1203ACIDSA

7、NDBASES1243.1BR~NSTEDACIDSANDBASES1243.2STRENGTHSOFWEAKBR~NSTEDBASES1293.3STRENGTHSOFWEAKBRDNSTEDACIDS1383.4SUBSTITUENTEFFECTSONSTRENGTHSOFBR~NSTEDACIDSAND/'BASES1503.5LEWISACIDSANDBASES163PROBLEMS1684BIMOLECULARSUBSTITUTIONREACTIONS1704.1SN1andSN2SUBSTITUTIONMECHANISMS1714.2STEREOCH