NUCLEOPHILIC DISPLACEMENTS UPON PHENYL ESTERS IN WHICH DIRECT RELATIONSHIP BETWEEN BASICITY OF LEAVING GROUP AND RATE IS DETERMINED BY GROUND-STATE CONFORMATIONS - QUESTION OF CONCERTED CATALYSIS IN HYDROLYSIS OF HEXACHLOROPHENE ESTERS

被引:9
作者
BRUICE, TC [1 ]
OKA, I [1 ]
机构
[1] UNIV CALIF,DEPT CHEM,SANTA BARBARA,CA 93106
关键词
D O I
10.1021/ja00821a025
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:4500 / 4507
页数:8
相关论文
共 33 条
[1]   INTERPRETATION OF PH MEASUREMENTS IN ALCOHOL-WATER SOLVENTS [J].
BATES, RG ;
BAABO, M ;
ROBINSON, RA .
JOURNAL OF PHYSICAL CHEMISTRY, 1963, 67 (09) :1833-&
[2]   KINETICS OF THE ACID AND ALKALINE HYDROLYSIS OF ETHOXYCARBONYLMETHYLTRIETHYLAMMONIUM CHLORIDE [J].
BELL, RP ;
LINDARS, FJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (DEC) :4601-4604
[3]   KINETICS OF ALKALINE HYDROLYSIS OF ETHYL ACETATE WITH SULPHUR CONTAINING SUBSTITUENTS [J].
BELL, RP ;
COLLER, BAW .
TRANSACTIONS OF THE FARADAY SOCIETY, 1965, 61 (511P) :1445-&
[4]   ELECTROSTATIC CATALYSIS - THE REACTIVITY OF AN ESTER AND A NUCLEOPHILE OF OPPOSITE CHARGE [J].
BENDER, ML ;
CHOW, YL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (15) :3929-3933
[5]  
BRUICE PY, IN PRESS
[6]   SOLVATION AND APPROXIMATION - SOLVENT EFFECTS ON BIMOLECULAR AND INTRAMOLECULAR NUCLEOPHILIC ATTACK OF CARBOXYL ANION ON PHENYL ESTERS [J].
BRUICE, TC ;
TURNER, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (11) :3422-&
[7]   IMIDAZOLE CATALYSIS .4. THE REACTION OF GENERAL BASES WITH PARA-NITROPHENYL ACETATE IN AQUEOUS SOLUTION [J].
BRUICE, TC ;
LAPINSKI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (09) :2265-2267
[8]   THE INFLUENCE OF THE LEAVING TENDENCY OF THE PHENOXY GROUP ON THE AMMONOLYSIS AND HYDROLYSIS OF SUBSTITUTED PHENYL ACETATES [J].
BRUICE, TC ;
MAYAHI, MF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (12) :3067-3071
[9]   HYDROXYL GROUP CATALYSIS .2. REACTIVITY OF HYDROXYL GROUP OF SERINE - NUCLEOPHILICITY OF ALCOHOLS AND EASE OF HYDROLYSIS OF THEIR ACETYL ESTERS AS RELATED TO THEIR PKA [J].
BRUICE, TC ;
BRUNO, JJ ;
BRANDON, NE ;
FIFE, TH .
BIOCHEMISTRY, 1962, 1 (01) :7-&
[10]   GEM EFFECT .4. ACTIVATION PARAMETERS ACCOMPANYING INCREASED STERIC REQUIREMENTS OF 3,5' SUBSTITUENTS IN SOLVOLYSIS OF MONO-P-BROMOPHENYL GLUTARATES [J].
BRUICE, TC ;
BRADBURY, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (14) :3808-&