MECHANISM AND CATALYSIS OF 2-METHYL-3-THIOSEMICARBAZONE FORMATION - SECOND CHANGE IN RATE-DETERMINING STEP AND EVIDENCE FOR A STEPWISE MECHANISM FOR PROTON-TRANSFER IN A SIMPLE CARBONYL ADDITION-REACTION

被引:122
作者
SAYER, JM [1 ]
JENCKS, WP [1 ]
机构
[1] BRANDEIS UNIV,GRAD DEPT BIOCHEM,WALTHAM,MA 02154
关键词
D O I
10.1021/ja00798a031
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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页码:5637 / 5649
页数:13
相关论文
共 74 条
[1]  
AHRENS ML, 1970, BERICH BUNSEN GESELL, V74, P380
[2]   ELEMENTARY STEPS IN ACID-BASE CATALYSIS . PROTON TRANSFER REACTIONS IN AQUEOUS SOLUTIONS [J].
AHRENS, ML ;
MAASS, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (10) :818-&
[3]   RATE-DETERMINING PROTON-TRANSFER IN INTRAMOLECULAR CATALYSIS OF AMIDE HYDROLYSIS BY CARBOXYLIC-ACID GROUP [J].
ALDERSLEY, MF ;
LANCASTE.PW ;
KIRBY, AJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (09) :570-+
[4]   THE EFFECT OF STRUCTURE ON REACTIVITY IN SEMICARBAZONE FORMATION [J].
ANDERSON, BM ;
JENCKS, WP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (07) :1773-1777
[5]  
ARCHILA J, 1971, J ORG CHEM, V36, P1345
[6]   DIFFUSION-CONTROLLED PROTON TRANSFER IN INTRAMOLECULAR THIOL ESTER AMINOLYSIS AND THIAZOLINE HYDROLYSIS [J].
BARNETT, RE ;
JENCKS, WP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (09) :2358-&
[7]   KINETICS OF DEHYDRATION OF METHYLENE GLYCOL IN AQUEOUS SOLUTION [J].
BELL, RP ;
EVANS, PG .
PROCEEDINGS OF THE ROYAL SOCIETY OF LONDON SERIES A-MATHEMATICAL AND PHYSICAL SCIENCES, 1966, 291 (1426) :297-+
[8]  
BELL RP, 1959, PROTON CHEMISTRY
[9]  
BELL RP, CITED INDIRECTLY
[10]  
BLACKBURN GM, 1970, CHEM COMMUN