EFFECTS ON ANIONS AND RADICALS OF ALPHA-QUATERNARY AMMONIUM SUBSTITUENTS

被引:37
作者
BORDWELL, FG
ZHANG, X
机构
[1] Department of Chemistry, Northwestern University, Evanston
关键词
D O I
10.1021/jo00312a008
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
α-Pyridinium groups increase the acidities of acetophenone, acetonitrile, and ethyl acetate much more than do α-Me3N+groups; they decrease the BDEs of the acidic C-H bonds, whereas a-Me3N+ groups increase them. © 1990, American Chemical Society. All rights reserved.
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页码:6078 / 6079
页数:2
相关论文
共 8 条
[1]   HOMOLYTIC BOND-DISSOCIATION ENERGIES IN SOLUTION FROM EQUILIBRIUM ACIDITY AND ELECTROCHEMICAL DATA [J].
BORDWELL, FG ;
CHENG, JP ;
HARRELSON, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1229-1231
[2]   EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].
BORDWELL, FG .
ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463
[3]   OXIDATION POTENTIALS OF CARBANIONS AND HOMOLYTIC BOND-DISSOCIATION ENERGIES OF THEIR CONJUGATE ACIDS [J].
BORDWELL, FG ;
HARRELSON, JA ;
SATISH, AV .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3101-3105
[4]   CARBON ACIDS .8. TRIMETHYLAMMONIO GROUP AS A MODEL FOR ASSESSING POLAR EFFECTS OF ELECTRON-WITHDRAWING GROUPS [J].
BORDWELL, FG ;
VANDERPUY, M ;
VANIER, NR .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (10) :1883-1885
[5]   PROPERTIES OF ANIONS, RADICALS, AND RADICAL CATIONS DERIVED FROM 9-(DIALKYLAMINO)FLUORENES [J].
BORDWELL, FG ;
CHENG, JP ;
SEYEDREZAI, SE ;
WILSON, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (24) :8178-8183
[6]  
BORDWELL FG, IN PRESS J AM CHEM S
[7]  
BORDWELL FG, IN PRESS CAN J CHEM
[8]   SUBSTITUENT EFFECTS ON BENZYL RADICAL HYPERFINE COUPLING-CONSTANTS .2. THE EFFECT OF SULFUR SUBSTITUENTS [J].
WAYNER, DDM ;
ARNOLD, DR .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (06) :1164-1168