生物化学23AromaticNitrogenCompou

生物化学23AromaticNitrogenCompou

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1、Chapter23AromaticNitrogenCompounds§23.1Nitroarenes23.1.1StructureofNitrobenzene23.1.2PreparationofNitrobenzeneWehavealreadyseenmanyexamplesofthepreparationofaromaticnitrocompounds.Byfarthemostimportantroutetosuchcompoundsiselectrophilicaromaticnitrati

2、onwithnitricacid.23.1.3PropertiesofNitroCompoundsNitrobenzeneandrelatednitrocompoundsaregenerallyhighboilingliquids.Nitrobenzenehaveacharacteristicodorofalmonds.Nitrobenzeneisreadilyabsorbedthroughtheskinandispoisonous.b.p.210–211℃Paleyellowoil2,4,6-T

3、rinitrotoluene, TNT,m.p.81℃TNTisanimportantexplosive.Itisrelativelyinsensitivetoshockandisusedwithadetonator(雷管,炸药).1,3,5-TrinitrobenzeneislesssensitivethanTNTtoshockandhasmoreexplosivepower,butismoredifficulttoprepare.23.1.4 ReactionsofNitroarenesRea

4、ctivitiesofNitroGroupThenitrogroupisrelativelystabletomanyreagents.Itisgenerallyinerttoacidsandmostelectrophilicreagents.Itisalsostabletomostoxidizingagents.ItreactswithRMgXandstronglybasicreagents.Themostimportantreactionofthenitrogroupinaromaticcomp

5、oundsisreduction.ReductionThereductionproductsdependsonthereactionconditionsused.MonomolecularReductionsofNitroarenesCatalytichydrogenationandchemicalreducingagentsinacidicmediagivethecorrespondingaminesinhighyield.常用:Fe/HClZn/HClInacidtheintermediate

6、compoundscannotbeisolated,butarereducedrapidlyinturn,Inneutralmedia,ahigherreductionpotentialisrequiredandreductionisreadilystoppedatthehydroxylaminestage.硝基苯还原关系图BimolecularReductionsofNitroarenesReductioninbasicmediagivesbinuclearcompounds.芳环上的亲核取代反

7、应Mechanism加成-消除机制§23.2Arylamines(AromaticAmines)23.2.1NomenclatureThreecommonarylamineshavethefollowingnames:23.2.2PhysicalPropertiesofArylaminesNameMp(℃)Bp(℃)pKaAniline-61844.58P-Toluidine442005.08P-Anisidine572445.30P-Chloroaniline732324.00P-Nitroan

8、iline1483321.00Diphenylamine533020.8023.2.3 PreparationofArylamines23.2.4BasicityofArylaminesArylaminesarelessbasicthanalkylaminesbecausethenitrogenlonepairelectronsaredelocalizedbyorbitaloverlapwiththearomaticringpielectronsystemandarelessava

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