KINETICS OF NITRIC ACID OXIDATION OF DIPHENYLMETHANE TO BENZOPHENONE

被引：18

作者：

OGATA, Y

TEZUKA, H

KAMEI, T

机构：

[1] Department of Applied Chemistry, Faculty of Engineering, Nagoya University, Chikusa-ku, Nagoya

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 04期

关键词：

D O I：

10.1021/jo01256a014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanism of nitric acid oxidation of diphenylmethane to benzophenone has been kinetically studied with ca. 2.5 M HNO2 in 70 vol. % aqueous acetic acid at 90°. The reaction shows an induction period, sodium nitrite being an effective initiator. At the nitrous acid concentration over 0.02 M, where the solution is probably saturated with NO2, the rate is expressed as v = K[C6H5CH2C6H5], i.e., the rates are independent of concentrations of nitric and nitrous acids. The k value increases with increasing acidity of the media, the plot of log k vs. H0 giving a straight line with a slope of ca. -1. A possible mechanism is proposed which involves a rate-determining abstraction of α-hydrogen atom from diphenylmethane by protonated NO2. © 1969, American Chemical Society. All rights reserved.

引用

页码：845 / &

共 8 条

[1]

BUCKLEY GD, 1949, J CHEM SOC, P1155

[2] FREE RADICALS BY MASS SPECTROMETRY .18. THE IONIZATION POTENTIALS OF CONJUGATED HYDROCARBON RADICALS AND THE RESONANCE ENERGIES OF RADICALS AND CARBONIUM IONS [J].