1. Synthesis and crystal structures of three new benzotriazolylpropanamides
- Author
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Donna S. Amenta, Phil Liebing, Julia E. Biero, Robert J. Sherman, John W. Gilje, and Frank T. Edelmann
- Subjects
crystal structure ,acrylamide ,benzotriazole ,benzotriazolylpropanamide ,hydrogen bond ,π–π stacking ,Crystallography ,QD901-999 - Abstract
The base-catalyzed Michael addition of 2-methylacrylamide to benzotriazole afforded 3-(1H-benzotriazol-1-yl)-2-methylpropanamide, C10H12N4O (1), in 32% yield in addition to small amounts of isomeric 3-(2H-benzotriazol-2-yl)-2-methylpropanamide, C10H12N4O (2). In a similar manner, 3-(1H-benzotriazol-1-yl)-N,N-dimethylpropanamide, C11H14N4O (3), was prepared from benzotriazole and N,N-dimethylacrylamide. All three products have been structurally characterized by single-crystal X-ray diffraction. The crystal structures of 1 and 2 comprise infinite arrays formed by N—H...O and N—H...N bridges, as well as π–π interactions, while the molecules of 3 are aggregated to simple π-dimers in the crystal.
- Published
- 2017
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