TAUTOMERIZATION ENERGETICS OF BENZOANNELATED TOLUENES

被引：34

作者：

BARTMESS, JE ^{[1
]}

GRIFFITH, SS ^{[1
]}

机构：

[1] INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1990年 / 112卷 / 08期

关键词：

D O I：

10.1021/ja00164a014

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The energy of tautomerization of some isotoluene structures has been measured by gas-phase ion/molecule reactions and by solution calorimetry. Benzoannelation appreciably destabilizes the aromatic tautomer, relative to the isotoluene form. An inverse saturation effect on the acidities of toluene, 1-methylnaphthalene, and 9-methylanthracene is observed. The p-isotoluene 3-methylene-1,4-cyciohexadiene appears to have the weakest C-H bond dissociation energy known, 64 ± 3 kcal/mol. Molecular orbital calculations bear out these results. © 1990, American Chemical Society. All rights reserved.

引用

页码：2931 / 2936

页数：6

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