The keto/enol equilibrium of phenol. An ab initio investigation

被引：22

作者：

Gadosy, TA ^{[1
]}

McClelland, RA ^{[1
]}

机构：

[1] UNIV TORONTO, DEPT CHEM, TORONTO, ON M5S 3H6, CANADA

来源：

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 1996年 / 369卷

关键词：

keto/enol equilibrium; phenol; ab initio;

D O I：

10.1016/S0166-1280(96)04694-5

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Ab initio 6-31G* basis set calculations have been carried out on phenol, 2,4-cyclohexadieneone and 2,5-cyclohexadieneone. Molecular geometries optimised at the restricted Hartree-Fock (RHF) level of theory indicate that all three structures are planar. Energy calculations were carried out using the RHF and second-order Moller-Plesset (MP2) formalisms, on the RHF optimised geometries. It was determined that phenol is significantly more stable than 2,4-cyclohexadieneone by 47.43 (RHF) and 72.51 (MP2) kJ mol(-1), and more stable than 2,5-cyclohexadieneone by 42.48 (RHF) and 70.61 (MP2) kJ mol(-1). From these results it is possible to estimate an equilibrium constant for phenol reversible arrow 2,4-cyclohexadieneone of 1.98 x 10(-13), which is in excellent agreement with experimental results.

引用

页码：1 / 8

页数：8

共 17 条

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