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Very-low-pressure pyrolysis of N-methyl aniline and N,N-dimethyl aniline. Enthalpy of formation of the anilino and N-methyl anilino radicals

✍ Scribed by A. J. Colussi; S. W. Benson

Publisher
John Wiley and Sons
Year
1978
Tongue
English
Weight
462 KB
Volume
10
Category
Article
ISSN
0538-8066

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✦ Synopsis

Abstract

The kinetics of the thermal unimolecular decompositions of N‐methyl aniline and N,N‐dimethyl aniline into anilino and N‐methyl anilino radicals, respectively, have been studied under very low‐pressure conditions. The enthalpies of formation of both radicals, Δ__H__°~f,298°K~(PhṄH,g) = 55.1 and Δ__H__°~f,298°K~(PhṄMe,g) = 53.2 kcal/mol, which have been derived from the experimental data, lead to BDE(PhNH‐H) = 86.4 ± 2, BDE[PhN(Me)‐H] = 84.9 ± 2 kcal/mol and to a value of 16.4 kcal/mol for the stabilization energy of the PhNH radical (relative to MeNH). These results are discussed in connection with earlier work. At high temperatures, the anilino radical loses HNC and forms the very stable cyclopentadienyl radical, a decomposition comparable to that of the phenoxy radical.

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