Syntheses, π-stacking interactions and base-pairings of uracil pyridinium salts and uracilyl betaines with nucleobases

…, M del Carmen Ruiz-Delgado, FJ Ramirez

Index: Schmidt, Andreas; Lindner, Anika; Nieger, Martin; Ruiz-Delgado, Maria Del Carmen; Ramirez, Francisco Javier Organic and Biomolecular Chemistry, 2006 , vol. 4, # 16 p. 3056 - 3066

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Citation Number: 12

Abstract

Reaction of 6-chlorouracil with 4-(dimethylamino) pyridine, 4-methylpyridine, and pyridin-4- yl-morpholine yielded pyridinium-substituted uracils as chlorides which were converted into pyridinium uracilates by deprotonation. These heterocyclic mesomeric betaines are cross- conjugated and thus possess separate cationic (pyridinium) and anionic (uracilate) moieties. Calculations and X-ray single crystal analyses were performed in order to characterize ...