Stabilization of benzene versus oligoacetylenes: not another scale for aromaticity

被引：8

作者：

Baldridge, KK ^{[1
]}

Siegel, JS ^{[1
]}

机构：

[1] Univ Zurich, Inst Organ Chem, CH-8006 Zurich, Switzerland

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 2004年 / 17卷 / 09期

关键词：

benzene; oligoacetylenes; aromaticity scale;

D O I：

10.1002/poc.819

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The energies of a number of oligoacetylenes are compared in a homodesmic reaction with benzene. Assessment of the open vs closed form of a conjugated triene is presented along with a perspective on the pursuit of quantitative scales for 'aromaticity'. Copyright (C) 2004 John Wiley Sons, Ltd.

引用

页码：740 / 742

页数：3

共 26 条

[1] WHY AROMATIC-COMPOUNDS ARE STABLE [J].

AIHARA, J .

SCIENTIFIC AMERICAN, 1992, 266 (03) :62-68

[2] EFFECT OF BOND-LENGTH ALTERNATION ON THE AROMATICITY OF BENZENE [J].

AIHARA, J .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (07) :1956-1960

[3] Why are some polycyclic aromatic hydrocarbons extremely reactive? [J].

Aihara, J .

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 1999, 1 (14) :3193-3197

[4] Ab initio density functional vs Hartree Fock predictions for the structure of [18]annulene: Evidence for bond localization and diminished ring currents in bicycloannelated [18]annulenes [J].

Baldridge, KK ;

Siegel, JS .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (07) :745-748

[5] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[6] AROMATICITY - EXERCISE IN CHEMICAL FUTILITY [J].

BINSCH, G .

NATURWISSENSCHAFTEN, 1973, 60 (08) :369-374

[7]

BINSCH G, 1971, JER S QUANT CHEM BIO, V3

[8]

BINSCH G, 1971, JERUSALEM S QUANTUM, V3, P25

[9] The relationship of classical and magnetic criteria of aromaticity [J].

Bird, CW .

TETRAHEDRON, 1996, 52 (29) :9945-9952

[10] Heteroaromaticity. 13. Bond alternation and its consequences for conjugation energies and other criteria of aromaticity [J].

Bird, CW .

TETRAHEDRON, 1998, 54 (18) :4641-4646

← 1 2 3 →