An Autogenic Electromeric Effect as Inductor of an Abnormal Polarization in Pyridine N-Oxide

Francisco Sánchez-Viesca^1, and Reina Gómez¹

¹Organic Chemistry Department, Faculty of Chemistry, National Autonomous University of Mexico, Mexico City (CDMX), México

Cite this paper:
Francisco Sánchez-Viesca and Reina Gómez. An Autogenic Electromeric Effect as Inductor of an Abnormal Polarization in Pyridine N-Oxide. World Journal of Chemical Education. 2017; 5(1):9-11. doi: 10.12691/wjce-5-1-2

Abstract

Nitration of pyridine N-oxide gives 4-nitropyridine N-oxide. This is an abnormal nitrone reactivity involving an electronic back-donation. However, the textbooks treat this result in a very brief way, without any insight. Which are the experimental antecedents of this reaction? What theory was proposed to explain them? What reactivity is overturned by these proposals? How theory and practice can come to agree on this subject? All these questions will be treated and answered in this communication.

Keywords:
nitrone reactivity electron back-donation 13-Cycloaddition 13-Dipolar structures Pyridine N- oxide

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