Cyclobutadiene: The antiaromatic paradigm?

被引：69

作者：

Bally, Thomas ^{[1
]}

机构：

[1] Univ Fribourg, Dept Chem, CH-1700 Fribourg, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 40期

关键词：

antiaromaticity; cyclobutadiene; thermochemistry;

D O I：

10.1002/anie.200602279

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The heat of formation of cyclobutadiene has recently been determined by Kass and co-workers. This determination is taken as an occasion to reflect on the difficulty to extract from this number the antiaromatic destabilization" and the strain energy of this most fundamental species. (Figure Presented). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA."

引用

页码：6616 / 6619

页数：4

共 33 条

[1]

Afeefy H.Y., 2005, NIST CHEM WEBBOOK NI

[2] ULTRAVIOLET AND POLARIZED INFRARED-SPECTROSCOPY OF MATRIX-ISOLATED CYCLOBUTADIENE AND ITS ISOTOPOMERS [J].

ARNOLD, BR ;

MICHL, J .

JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (50) :13348-13354

[3]

ARNOLD BR, 1990, KINETICS SPECTROSCOP, P20

[4] Strain energy of small ring hydrocarbons. Influence of C-H bond dissociation energies [J].

Bach, RD ;

Dmitrenko, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4444-4452

[5] A MULTIREFERENCE COUPLED-CLUSTER STUDY OF THE GROUND-STATE AND LOWEST EXCITED-STATES OF CYCLOBUTADIENE [J].

BALKOVA, A ;

BARTLETT, RJ .

JOURNAL OF CHEMICAL PHYSICS, 1994, 101 (10) :8972-8987

[6] CYCLOBUTADIENE [J].

BALLY, T ;

MASAMUNE, S .

TETRAHEDRON, 1980, 36 (03) :343-370

[7]

Benson S.W., 1968, THERMOCHEMICAL KINET

[8] HEAVY-ATOM TUNNELING AS THE DOMINANT PATHWAY IN A SOLUTION-PHASE REACTION - BOND SHIFT IN ANTIAROMATIC ANNULENES [J].

CARPENTER, BK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (06) :1700-1701

[9] Experimental determination of the antiaromaticity of cyclobutadiene [J].

Deniz, AA ;

Peters, KS ;

Snyder, GJ .

SCIENCE, 1999, 286 (5442) :1119-1122

[10] CHEMICAL IMPLICATIONS OF SIGMA-CONJUGATION [J].

DEWAR, MJS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (03) :669-682

← 1 2 3 4 →