STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .19. RELATIVE ELECTRON RELEASING CAPABILITY OF METHYL, PHENYL, AND CYCLOPROPYL GROUPS AS MEASURED BY TOOL OF INCREASING ELECTRON DEMAND

被引：29

作者：

BROWN, HC ^{[1
]}

RAVINDRANATHAN, M ^{[1
]}

PETERS, EN ^{[1
]}

机构：

[1] PURDUE UNIV,RICHARD B WETHERILL LAB,W LAFAYETTE,IN 47907

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1977年 / 42卷 / 06期

关键词：

D O I：

10.1021/jo00426a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

引用

页码：1073 / 1076

页数：4

共 20 条

[1] DIRECTIVE EFFECTS IN AROMATIC SUBSTITUTION .30. ELECTROPHILIC SUBSTITUENT CONSTANTS [J].

BROWN, HC ;

OKAMOTO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (18) :4979-4987

[2] RATES OF SOLVOLYSIS OF 2-METHYL-2-PROPYL PARA-NITROBENZOATES, 2-TERT-BUTYL-2-PROPYL PARA-NITROBENZOATES, 2-PHENYL-2-PROPYL PARA-NITROBENZOATES, AND 2-CYCLOPROPYL-2-PROPYL PARA-NITROBENZOATES - EVIDENCE THAT C-13 CHEMICAL-SHIFTS OF CARBONIUM-IONS DO NOT CORRELATE WITH STABILITIES OF SOLVOLYTIC TRANSITION-STATES AND CORRESPONDING CATIONIC INTERMEDIATESB [J].

BROWN, HC ;

PETERS, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (07) :2400-2402

[3] SOLVOLYSIS OF 3-ARYL-3-NORTRICYCLYL P-NITROBENZOATES - EVIDENCE FOR MAJOR INCREASES IN ELECTRON SUPPLY BY CYCLOPROPYL GROUP WITH INCREASING ELECTRON DEMAND AT CATIONIC CENTER [J].

BROWN, HC ;

PETERS, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (07) :1927-1929

[4] STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .18. RELATIVE ELECTRON RELEASING PROPERTIES OF METHYL, PHENYL, AND CYCLOPROPYL GROUPS TO ELECTRON DEFICIENT CENTER AS INDICATED BY SOLVOLYSIS - CRITICAL-EXAMINATION OF C-13 CHEMICAL-SHIFTS AS A BASIS FOR ESTABLISHING ELECTRON-DENSITIES IN CARBONIUM-IONS [J].

BROWN, HC ;

PETERS, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (06) :1712-1716

[5] HIGH EXO - ENDO RATE RATIO AND PREDOMINANT EXO SUBSTITUTION IN SOLVOLYSIS OF 2-P-ANISYLNORBORNYL DERIVATIVES . CHARACTERISTICS OF A HIGHLY STABILIZED CLASSICAL NORBORNYL CATION [J].

BROWN, HC ;

TAKEUCHI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (10) :2691-&

[6] STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .11. RATES AND PRODUCTS OF SOLVOLYSIS OF 2-ARYL-2-NORBORNENYL-PARA-NITROBENZOATES AND 2-METHYL-2-NORBORNENYL PARA-NITROBENZOATES - EXO-ENDO RATE RATIO AS A FUNCTION OF INCREASING ELECTRON DEMAND [J].

BROWN, HC ;

PETERS, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (26) :7442-7448

[7] STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .12. SOLVOLYSIS OF 2-ARYL-5-METHYL-2-NORBORNENYL-PARA-NITRO-BENZOATES AND 2,5-DIMETHYL-2-NORBORNENYL PARA-NITROBENZOATES - EVIDENCE FOR MAJOR PI PARTICIPATION REVEALED BY TOOL OF INCREASING ELECTRON DEMAND [J].

BROWN, HC ;

PETERS, EN ;

RAVINDRANATHAN, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (26) :7449-7453

[8]

BROWN HC, 1975, J AM CHEMICAL SOC, V97, P7454

[9]

BROWN HC, IN PRESS

[10] CARBON-13 MAGNETIC RESONANCE .8. THEORY OF CARBON-13 CHEMICAL SHIFTS APPLIED TO SATURATED HYDROCARBONS [J].

CHENEY, BV ;

GRANT, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (21) :5319-&

← 1 2 →