HETEROCYCLES

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■ The Electrophilic Substitution of Heteroaromatic Compounds. Part 53. The Experimental Orientation in the Electrophilic Substitution of 1-Phenylpyridinium Cations, and a Theretical Treatment of Electrophilic Substitution Orientations in N-Phenylheterocycles

Alan R. Katritzky,* Hassan M. Faid-Allah, Hudson Luce, Mati Karelson, and George P. Ford

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, P. O. Box 117200, Gainesville, FL 32611-7200, U.S.A.

Abstract

Nitration, sulfonation and bromination of the title compound occur in the meta position of the 1-phenyl group. This meta substitution, and the para substitution previously observed for other N-phenylheterocycles, cannot be explained by static reactivity indices. However, a MNDO analysis, taking account of the near degeneracy of the two top HOMO’s, and using experimentally probable interannular anglee, allows rationalization of the orientations observed.