KINETICS AND MECHANISM OF AROMATIC ELECTROPHILIC SUBSTITUTION-REACTIONS .4. DIVISION OF METHYLBENZENE REACTIONS INTO BASICITY-VERSUS IONIZATION POTENTIAL-CONTROLLED REACTIONS

被引：0

作者：

RUDAKOV, ES

LOBACHEV, VL

机构：

来源：

KINETICS AND CATALYSIS | 1990年 / 31卷 / 06期

关键词：

D O I：

暂无

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Electrophilic aromatic substitution reactions have been divided into three classes based on data obtained for substrate selectivity in the first stage of reactions in the series benzene to hexamethylbenzene: weakly or nonselective reactions, selective reactions controlled by arene basicity, and selective reactions controlled by ionization potential. Based on the results of kinetic isotope effects and product composition we have proposed a generalized reaction scheme for these types of reactions, involving as key intermediates either a sigma-complex between the arene and electrophilic reagent or a charge transfer complex. The criteria underlying mechanism selection are discussed.

引用

页码：1138 / 1144

页数：7

共 34 条

[1] KINETICS AND MECHANISM OF THE ADDITION OF TRIPHENYLPHOSPHONIOCYCLOPENTADIENIDE TO TETRAHALOGENO-P-BENZOQUINONES .4. THE SUBSTITUTION-REACTIONS OF FLUORANIL
PLA, FP
HALL, CD
SPEERS, P
PALOU, J
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (12): : 2499 - 2506
[2] THE KINETICS AND MECHANISM OF AROMATIC ELECTROPHILIC SUBSTITUTION-REACTIONS .6. THE TEMPERATURE-DEPENDENCE OF SUBSTRATE SELECTIVITY OF BENZENE AND METHYLBENZENE NITRATION IN THE SYSTEM HNO3-H2SO4 (63.8 WT PERCENT)
RUDAKOV, ES
LOBACHEV, VL
TSERKOVNIKOV, SA
KINETICS AND CATALYSIS, 1993, 34 (03) : 383 - 386
[3] KINETICS AND MECHANISM OF PHOTOCHEMICAL SUBSTITUTION-REACTIONS OF CP2FE2(CO)4
ZHANG, SL
BROWN, TL
ORGANOMETALLICS, 1992, 11 (12) : 4166 - 4173
[4] STUDIES OF SUBSTRATE SELECTIVITY IN AROMATIC IODINATION AND OTHER SUBSTITUTION-REACTIONS REINFORCE PREVIOUS CONCLUSIONS ABOUT THE NATURE OF THE MECHANISM OF ELECTROPHILIC AROMATIC SUBSTITUTIONS
GALLI, C
DIGIAMMARINO, S
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (06): : 1261 - 1269
[5] RELATIONSHIP OF ACTIVITY AND SELECTIVITY IN ELECTROPHILIC SUBSTITUTION-REACTIONS IN 5-MEMBERED HETEROAROMATIC-COMPOUNDS .4. THE MECHANISM FOR THE TRANSMISSION OF ELECTRONIC EFFECTS
GORB, LG
MOROZOVA, IM
BELENKII, LI
ABRONIN, IA
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1983, 32 (09): : 1791 - 1795
[6] KINETICS AND MECHANISM OF AROMATIC ELECTROPHILIC SUBSTITUTION-REACTIONS .1. INTERACTION OF METHYLBENZENES WITH NITROUS-ACID IN H2SO4-H2O MEDIUM
LOBACHEV, VL
RUDAKOV, ES
SAVSUNENKO, OB
KINETICS AND CATALYSIS, 1990, 31 (04) : 690 - 695
[7] Kinetics and mechanism of aromatic electrophilic substitution reactions:: VII.: Temperature dependence of substrate selectivity of methylbenzene hydroxylation in the system H2O2-H2SO4
Rudakov, ES
Lobachev, VL
KINETICS AND CATALYSIS, 2000, 41 (02) : 196 - 200
[8] Kinetics and mechanism of aromatic electrophilic substitution reactions: VII. Temperature dependence of substrate selectivity of methylbenzene hydroxylation in the system H2O2-H2SO4
E. S. Rudakov
V. L. Lobachev
Kinetics and Catalysis, 2000, 41 : 196 - 200
[9] KINETICS AND MECHANISM OF AROMATIC ELECTROPHILIC SUBSTITUTION-REACTIONS .3. SUBSTRATE AND POSITIONAL SELECTIVITY IN THE NITRATION OF ANISOLE, CHLORO-BENZENES, AND IODOBENZENES IN THE SYSTEM ACONO2-CCL4
RUDAKOV, ES
LOBACHEV, VL
SAVSUNENKO, OB
KINETICS AND CATALYSIS, 1990, 31 (05) : 938 - 944
[10] KINETICS AND MECHANISM OF AROMATIC ELECTROPHILIC SUBSTITUTION-REACTIONS .2. INTERACTION OF METHYLBENZENES WITH NITROUS-ACID IN CF3COOH-H2O MEDIUM
RUDAKOV, ES
LOBACHEV, VL
SAVSUNENKO, OB
KINETICS AND CATALYSIS, 1990, 31 (04) : 695 - 701

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