THE MAGNITUDE OF DESTABILIZATION OF STABILIZED CATIONS BY CYANO AND TRIFLUOROMETHYL GROUPS

被引:29
作者
PADDONROW, MN
HOUK, KN
TIDWELL, TT
机构
[1] UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260
[2] UNIV TORONTO,SCARBOROUGH COLL,W HILL M1C 1A4,ONTARIO,CANADA
关键词
D O I
10.1016/S0040-4039(00)86837-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:383 / 386
页数:4
相关论文
共 15 条
[1]  
ALLAN A, UNPUB
[2]  
BEGUE JP, 1980, ACCOUNTS CHEM RES, V13, P207, DOI 10.1021/ar50151a003
[3]   GENERATION OF ALPHA-KETO CATIONS - QUANTITATIVE ASPECTS [J].
CREARY, X .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22) :3938-3945
[4]   STABILIZATION OF ALPHA-KETO CATIONS BY CARBONYL CONJUGATION [J].
CREARY, X .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) :2463-2465
[5]   MESOMERIC STABILIZATION OF CARBONIUM-IONS BY ALPHA-CYANO GROUPS - A THEORETICAL EVALUATION OF INDUCTIVE VS RESONANCE EFFECTS OF THE CYANO MOIETY [J].
DIXON, DA ;
CHARLIER, PA ;
GASSMAN, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (11) :3957-3959
[6]   SOLVOLYSIS OF ADAMANTANONE CYANOHYDRIN SULFONATES - AN EVALUATION OF H-ALPHA-CN VS H-BETA-CN RATE RATIOS [J].
GASSMAN, PG ;
SAITO, K ;
TALLEY, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (25) :7613-7615
[7]   ALPHA-CYANO GROUP AS A SUBSTITUENT IN SOLVOLYSIS REACTIONS - EVALUATION OF INDUCTIVE DESTABILIZATION VS MESOMERIC STABILIZATION OF CATIONS BY THE CYANO MOIETY [J].
GASSMAN, PG ;
TALLEY, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (03) :1214-1216
[8]   EFFECT OF ALPHA-CYANO GROUPS ON NEIGHBORING GROUP PARTICIPATION IN CARBONIUM-ION REACTIONS [J].
GASSMAN, PG ;
TALLEY, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (12) :4138-4143
[9]   SOLVOLYTIC REACTIVITY OF ALPHA-TRIFLUOROMETHYLCARBINYL SULFONATES - CORRELATION OF RATE RETARDATION BY ELECTRON-WITHDRAWING SUBSTITUENTS AND SOLVENT PARTICIPATION IN TERTIARY SUBSTRATES [J].
KOSHY, KM ;
TIDWELL, TT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (03) :1216-1218
[10]  
LATHAN WA, 1974, PROGR PHYS ORG CHEM, V11, P175