AROMATICITY AND ANTIAROMATICITY IN 5-MEMBERED C(4)H(4)X RING-SYSTEMS - CLASSICAL AND MAGNETIC CONCEPTS MAY NOT BE ORTHOGONAL

被引：453
作者：
SCHLEYER, PV [1 ]
FREEMAN, PK [1 ]
JIAO, HJ [1 ]
GOLDFUSS, B [1 ]
机构：
[1] OREGON STATE UNIV, DEPT CHEM, CORVALLIS, OR 97331 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 1995年 / 34卷 / 03期
关键词：
AB INITIO CALCULATIONS; AROMATICITY; HETEROCYCLES;
D O I：
10.1002/anie.199503371
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Energetic, geometric, and magnetic criteria yield quantitatively the same order of aromaticity (antiaromaticity) for the five‐membered ring systems 1: the aromatic 6π electron systems are stabilized, their bond lengths are equalized, and the magnetic susceptibility exaltations are diamagnetic. In contrast, the antiaromatic 4π electron systems are destabilized, double bonds are localized, and susceptibility exaltations are paramagnetic. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
引用
收藏
页码：337 / 340
页数：4
相关论文
共 80 条
[1]  
Acheson R. M., 1976, INTRO CHEM HETEROCYC
[2]  
[Anonymous], 1986, AB INITIO MOL ORBITA
[3]  
BACHRACH SM, 1993, J ORG CHEM, V58, P541
[4]  
BACHRACH SM, 1994, J ORG CHEM, V59, P3349
[5]   POTENTIALLY AROMATIC METALLOCYCLES [J].
BALDRIDGE, KK ;
GORDON, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (13) :4204-4208
[6]  
Benson R. C., 1970, Journal of the American Chemical Society, V92, P7523, DOI 10.1021/ja00729a001
[7]  
Bernardi F, 1988, J MOL STRUC-THEOCHEM, V163, P173
[8]   SYNTHESIS AND STUDY OF PSEUDO-AROMATIC COMPOUNDS .3. CORRELATION OF NUCLEAR MAGNETIC RESONANCE SOLVENT SHIFTS WITH PI-ELECTRONIC DELOCALIZATION ENERGIES IN AROMATIC COMPOUNDS [J].
BERTELLI, DJ ;
GOLINO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (02) :368-&
[9]   HETEROAROMATICITY .6. THE EFFECT OF MOLECULAR DISTORTION ON AROMATICITY [J].
BIRD, CW .
TETRAHEDRON, 1992, 48 (09) :1675-1682
[10]   HETEROAROMATICITY .5. A UNIFIED AROMATICITY INDEX [J].
BIRD, CW .
TETRAHEDRON, 1992, 48 (02) :335-340
12345678