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■ Modified Uracils Convertible between Cations, Conjugated, and Cross-conjugated Mesomeric Betaines. Syntheses, Semiempirical Study, and X-Ray Analysis

Andreas Schmidt,* Markus Karl Kindermann, and Martin Nieger

*Laboratorium für Organische und Bioorganische, Institut für Chemie, Universität Osnabrück, Barbarastr. 7, D-4500 Osnabrück, Germany

Abstract

Nucleophilic substitution on the 6-chiorouracils (1) and (8) by heteroaromatics such as DMAP, 4-methylpyridine, and 3-hydroxypyridine yielded uracilylpyridinium salts (2, 3, 7, 10), mesomeric betaines (4, 5, 6), and a bis-betaine (9), respectively. A prototropic shift converts the CCMB (6A) into the CMB (6B), the dipole moments and most stable conformations of which were calculated. X-Ray crystallography was performed on the uracilylpyridinium salt (7).