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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Electrophilic Substitution In Azines

Author(s): M. D'Auria

Volume 2, Issue 7, 2005

Page: [659 - 661] Pages: 3

DOI: 10.2174/157017805774296849

Price: $65

Abstract

The low reactivity of pyridine, pyridazine, pyrazine, and pyrimidine towards electrophilic substitution reactions can be explained assuming a frontier orbitals control of the reaction. In fact, DFT study of the molecular orbitals of these molecules shows that the HOMOs of these substrates are not π orbitals. Furthermore, the change in the reactivity observed in pyridine-N-oxide can be explained considering that, in this case, the HOMO is an aromatic orbital.

Keywords: pyridine, pyrazine, pyridazine, pyrimidine, electrophilic substitution, dft


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