生物化學(xué)23aromaticnitrogencompou(編輯修改稿)
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【文章內(nèi)容簡介】 ine 53 302 Preparation of Arylamines ( C H3)3C N O2H2 , P tE t O H( C H3)3C N H2C H3N O2O2NF e , H C lC H3N H2H2NB rO2NN O2R N H2N H RO2NN O2N HOOX2N a O HN H2C O2HC H3N O2N O2H2S , N H3C H3N H2N O2 Basicity of Arylamines ? Arylamines are less basic than alkylamines because the nitrogen lonepair electrons are delocalized by orbital overlap with the aromatic ring pi electron system and are less available for bonding. ? As a general rule, substituents that increase the reactivity of an aromatic ring toward electrophilic substitution also increase the basicity of the corresponding arylamine. N H2O HC H3HC lB rC NN O26 . 1 55 . 3 45 . 0 84 . 6 33 . 9 83 . 8 61 . 7 41 . 0 0A c t i v a t i n gg r o u p sD e a c t i v a t i n gg r o u p sS u b s t i t u e n t s , Y p K aN H 2Y + H 2 O N H 3Y + O HStronger base Weaker base Reactions of Arylamines ? Electrophilic Aromatic Substitution ? Oxidation ? Benzidine(對二氨基聯(lián)苯 )Rearrangement ? Diazotization Electrophilic Aromatic Substitution ? Amino substituents are strongly activating groups in electrophilic aromatic substitution reactions. N H 2B r2H2ON H2B rB rB rA n i l i n e 2 , 4 , 6 T r i b r o m o a n i l i n e100% N H2( C H3C O )2OP y r i d i n eN H C O C H3N H C O C H3B r2B rH2OH C lN H2B r+ C H3C O2HN H2I2N a H C O3N H2I? Friedel Crafts Reactions of Aminosubstituted Benzene Are Not Successful. N H 2 N H2 A l C l 3A l C l 3+N H 2( C H 3 C O ) 2 OP y r i d i n eN H C O C H 3 N H C O C H3C O C 6 H 5A l C l 3C 6 H 5 C O C lN H2室 溫發(fā) 煙 H2S O4N H2S O3HN H C O C H3C l S O3H8 0 ℃N H C O C H3S O2C l( 1 ) R N H2N H2S O2N H R( 2 ) H C l對 氨 基 苯 磺 酰 胺S u l f o n i l a m i d e( a s u l f a d r u g )R = H 磺 胺 =C O C H3NSNNNO C H3對 乙 酰 氨 基 苯 磺 酰 胺 S A磺 胺 噻 唑 ( S T ) 磺 胺 甲 基 異 惡 唑 ( S M Z ) 磺 胺 嘧 啶 ( S T )N H C O C H3N H C O C H3 N H C O C H 3+N O2N O2硝 化 試 劑硝 化 試 劑H N O3 H2S O41 0 % 9 0 %9 0 % H N O3/ 2 0 ℃2 3 ％ 7 7 ％H N O3 A c2O / 2 0 ℃ 6 8 %
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鄂ICP備17016276號-1