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Theoretical study concerning the reactivity of imine derivatives of polycyclic aromatic hydrocarbons

✍ Scribed by Gabriela L. Borosky

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
137 KB
Volume
24
Category
Article
ISSN
0192-8651

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✦ Synopsis

Abstract

The opening reaction of N‐protonated polycyclic aromatic hydrocarbon imines has been computed by means of ab initio, density functional, and semiempirical methods of calculation. Imines are predicted to be more stable than the corresponding O‐protonated derivatives, epoxides and diol epoxides. On the other hand, the activated N‐methanesulfonylbenzene imine presented more favorable Δ__E__^≠^ and Δ__E__~r~ for ring opening due to the effect of hydrogen‐bond interactions. Anti and syn trans‐diol benzene imines did not show a different behavior from the unsubstituted imine. According to these calculations, bay‐region, fjord‐region, and bay‐region methyl‐substituted compounds opened more easily among the imine derivatives, following the same reactivity pattern as the oxygen analogs. The exothermicity of the opening process correlated with the charge delocalization in the resulting carbocation. © 2003 Wiley Periodicals, Inc. J Comput Chem 24: 601–608, 2003

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