ASPECTS OF ELECTROPHILIC BROMINATION OF ALKENES IN SOLUTION - THEORETICAL CALCULATION OF ATOMIC CHARGES IN BROMONIUM IONS

被引：42

作者：

COSSI, M ^{[1
]}

PERSICO, M ^{[1
]}

TOMASI, J ^{[1
]}

机构：

[1] UNIV PISA,DIPARTIMENTO CHIM & CHIM IND,I-56126 PISA,ITALY

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1994年 / 116卷 / 12期

关键词：

D O I：

10.1021/ja00091a048

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first results of a theoretical study of bromination reactions in solution are presented, with an illustration of the parameters used to describe the solvation effects in the framework of the polarizable continuum model (PCM). The distribution of the positive charge on the atoms of some bromonium ions is calculated, using Bader's procedure on the wave functions obtained in vacuo, in dichloroethane, and in methanol. These results provide new insights about the nature of bromonium ions and the reversibility of their formation reactions.

引用

页码：5373 / 5378

页数：6

共 44 条

[1] SOLUTE-SOLVENT INTERACTIONS - A SIMPLE PROCEDURE FOR CONSTRUCTING THE SOLVENT CAVITY FOR RETAINING A MOLECULAR SOLUTE [J].

AGUILAR, MA ;

DELVALLE, FJO .

CHEMICAL PHYSICS, 1989, 129 (03) :439-450

[2] ATOMS IN MOLECULES [J].

BADER, RFW .

ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (01) :9-15

[3] QUANTUM-THEORY OF ATOMS IN MOLECULES - DALTON REVISITED [J].

BADER, RFW ;

NGUYENDANG, TT .

ADVANCES IN QUANTUM CHEMISTRY, 1981, 14 :63-124

[4] STRUCTURE AND ENERGETICS OF SIMPLE CARBENES CH2, CHF, CHCL, CHBR, CF2, AND CCL2 [J].

BAUSCHLICHER, CW ;

SCHAEFER, HF ;

BAGUS, PS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (22) :7106-7110

[5] DIRECT EVIDENCE FOR BROMINE OLEFIN CHARGE-TRANSFER COMPLEXES AS ESSENTIAL INTERMEDIATES OF THE FAST IONIC ADDITION OF BROMINE TO CYCLOHEXENE [J].

BELLUCCI, G ;

BIANCHINI, R ;

AMBROSETTI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (08) :2464-2471

[6] FORMATION OF PENTABROMIDE IONS FROM BROMINE AND BROMIDE IN MODERATE-POLARITY APROTIC-SOLVENTS AND THEIR POSSIBLE INVOLVEMENT IN THE PRODUCT-DETERMINING STEP OF OLEFIN BROMINATION [J].

BELLUCCI, G ;

BIANCHINI, R ;

CHIAPPE, C ;

AMBROSETTI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (01) :199-202

[7] THE SOLUTION BEHAVIOR OF THE ADAMANTYLIDENEADAMANTANE BROMINE SYSTEM - EXISTENCE OF EQUILIBRIUM MIXTURES OF BROMONIUM POLYBROMIDE SALTS AND A STRONG 1-1 MOLECULAR CHARGE-TRANSFER COMPLEX [J].

BELLUCCI, G ;

BIANCHINI, R ;

CHIAPPE, C ;

MARIONI, F ;

AMBROSETTI, R ;

BROWN, RS ;

SLEBOCKATILK, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) :2640-2647

[8] COMPARISON OF MOLECULAR BROMINE AND TRIBROMIDE ION AS BROMINATING REAGENTS .1. KINETIC EVIDENCE FOR DIFFERENT MECHANISMS OF ADDITION TO CYCLOHEXENE [J].

BELLUCCI, G ;

BIANCHINI, R ;

AMBROSETTI, R ;

INGROSSO, G .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (18) :3313-3318

[9] CALCULATION OF THE AVERAGE PROPERTIES OF ATOMS IN MOLECULES .2. [J].

BIEGLERKONIG, FW ;

BADER, RFW ;

TANG, TH .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1982, 3 (03) :317-328

[10] ABINITIO EVALUATION OF ABSORPTION AND EMISSION TRANSITIONS FOR MOLECULAR SOLUTES, INCLUDING SEPARATE CONSIDERATION OF ORIENTATIONAL AND INDUCTIVE SOLVENT EFFECTS [J].

BONACCORSI, R ;

CIMIRAGLIA, R ;

TOMASI, J .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1983, 4 (04) :567-577

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