Title of article :
Synthesis and crystal structures of three new benzotriazolylpropanamides
Author/Authors :
Amenta, Donna S. Chemistry Department - James Madison University, USA , Biero, Julia E. Chemistry Department - James Madison University, USA , Liebing, Phil Chemisches Institut der Otto-von-Guericke-Universität Magdeburg, Germany , Sherman, Robert J. Chemistry Department - James Madison University, USA , Gilje, John W. Chemistry Department - James Madison University, USA , Edelmann, Frank T. Chemisches Institut der Otto-von-Guericke-Universität Magdeburg, Germany
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.
Keywords :
crystal structure , acrylamide , benzotriazole , benzotriazolylpropanamide , hydrogen bond , π–π stacking
Journal title :
Acta Crystallographica Section E: Crystallographic Communications
