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Ch18 Amines(pdf) - KFUPM Open Courseware

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Effect is CumulativeHeterocyclic <strong>Amines</strong>Aniline is 3800 times more basic thanp-nitroaniline.Aniline is ~1,000,000,000 times more basic than2,4-dinitroaniline.••NHpiperidineis more basic thanN ••pyridineK b = 1.6 x 10 -3 K b = 1.4 x 10 -9(an alkylamine)(resembles anarylamine inbasicity)Heterocyclic <strong>Amines</strong>Imidazole••N•• NHis more basic thanN ••Which nitrogen is protonated in imidazole?••N•• NHimidazolepyridineK b = 1 x 10 -7 K b = 1.4 x 10 -9H + H +H+N • N H••N+NHH

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