NMR-STUDIES OF BOND ORDER IN DISTORTED AROMATIC SYSTEMS

被引：25

作者：

GREADY, JE

HAMBLEY, TW

KAKIUCHI, K

KOBIRO, K

STERNHELL, S

TANSEY, CW

TOBE, Y

机构：

[1] UNIV SYDNEY,DEPT ORGAN CHEM,SYDNEY,NSW 2006,AUSTRALIA

[2] OSAKA UNIV,FAC ENGN,DEPT APPL FINE CHEM,SUITA,OSAKA 565,JAPAN

[3] UNIV SYDNEY,DEPT BIOCHEM,SYDNEY,NSW 2006,AUSTRALIA

[4] UNIV SYDNEY,DEPT CHEM,SYDNEY,NSW 2006,AUSTRALIA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1990年 / 112卷 / 21期

关键词：

D O I：

10.1021/ja00177a013

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 4JH-C⩵C-Mecoupling constant has been previously established1,2as a probe of bond order. This has now been used to examine the bond orders of compounds containing severely distorted benzene nuclei. In the case of 3,4-di-tert-butyltoluene, no electronic distortions in the aromatic ring can be detected by this method. A series of moderately to severely distorted paracyclophanes show no perturbation of electronic structure, with the possible exception of 8-methyl [6]paracyclophane, which exhibits a barely significant deviation from unstrained values. These conclusions are supported by the results of SCF-MO calculations. © 1990, American Chemical Society. All rights reserved.

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页码：7537 / 7540

页数：4

相关论文

共 17 条

[1] NMR-STUDIES OF BOND-ORDERS [J].

BARFIELD, M ;

COLLINS, MJ ;

GREADY, JE ;

HATTON, PM ;

STERNHELL, S ;

TANSEY, CW .

PURE AND APPLIED CHEMISTRY, 1990, 62 (03) :463-466

[2] BOND-ORDER DEPENDENCE OF ORTHOBENZYLIC COUPLING-CONSTANTS INVOLVING A METHYL-GROUP [4J(MEC=CH)] [J].

BARFIELD, M ;

COLLINS, MJ ;

GREADY, JE ;

STERNHELL, S ;

TANSEY, CW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4285-4290

[3] LIN-POLY-PARA-XYLYLENE .2. THE CRYSTAL STRUCTURE OF DI-P-XYLYLENE [J].

BROWN, CJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1953, (OCT) :3265-3270

[4] SUBSTITUENT AND RING SIZE DEPENDENCE OF THE 4J(ME-C=C-H) COUPLING-CONSTANT [J].

COLLINS, MJ ;

HATTON, PM ;

STERNHELL, S ;

TANSEY, CW .

MAGNETIC RESONANCE IN CHEMISTRY, 1987, 25 (09) :824-828

[5] MACRO RINGS .33. A 1,6 TO 1,6 CYCLOADDITION REACTION A DIELS-ALDER INSERTION REACTION AND BENT BENZENE RINGS [J].

CRAM, DJ ;

MONTGOME.CS ;

KNOX, GR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (03) :515-&

[6] THE VALUE OF THE PI-BOND ORDER BOND LENGTH RELATIONSHIP IN GEOMETRY PREDICTION AND CHEMICAL BONDING INTERPRETATION [J].

GREADY, JE .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1984, 5 (05) :411-426

[7]

Greenberg A., 1978, STRAINED ORGANIC MOL, V1st

[8] PI-ORBITAL CONJUGATION AND REHYBRIDIZATION IN BRIDGED ANNULENES AND DEFORMED MOLECULES IN GENERAL - PI-ORBITAL AXIS VECTOR ANALYSIS [J].

HADDON, RC ;

SCOTT, LT .

PURE AND APPLIED CHEMISTRY, 1986, 58 (01) :137-142

[9] REHYBRIDIZATION AND PI-ORBITAL OVERLAP IN NONPLANAR CONJUGATED ORGANIC-MOLECULES - PI-ORBITAL AXIS VECTOR (POAV) ANALYSIS AND 3-DIMENSIONAL HUCKEL MOLECULAR-ORBITAL (3D-HMO) THEORY [J].

HADDON, RC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (06) :1676-1685

[10]

HAMA F, 1984, B CHEM SOC JPN, V57, P3557