Title of article :
Crystal structures of (1E,4E)-1,5-bis(5-bromothiophen-2-yl)-2,4-dimethylpenta-1,4-dien-3-one and (E)-4-(5-bromothiophen-2-yl)-1,3-diphenylbut-3-en-2-one
Author/Authors :
Nithya, C. Department of Applied Chemistry - Cochin University of Science and Technology, India , Sithambaresan, M. Department of Chemistry - Faculty of Science - Eastern University, Chenkalady, Sri Lanka , Prathapachandra Kurup, M. R. Department of Applied Chemistry - Cochin University of Science and Technology, India
Abstract :
The title compounds, C15H12Br2OS2, (I), and C20H15BrOS, (II), were synthesized by employing Claisen–Schmidt condensation of pentan-3-one and dibenzylacetone with 5-bromothiophene-2-carbaldehyde in the presence of methanolic KOH. Even though 1:2 products were expected in both of the reactions, 1:2 and 1:1 products were obtained as (I) and (II), respectively. In (I), the two methyl groups are trans to each other, 29.5 (7) and 28.7 (7)° away from the central carbonyl bond between them, whereas the two phenyl rings of dibenzylacetone subtend a dihedral angle of 53.09 (18)°. In the crystal of (I), C—H⋯O hydrogen bonds define molecular chains along c. A second type of molecular chain is formed along b by means of C—Br⋯π interactions. These two families of molecular chains are stacked by π–π interactions, forming a three-dimensional supramolecular architecture. In (II), similar C—H⋯O hydrogen bonds as in (I) define inversion dimers, whilst C—H⋯.π interactions build a staircase structure along the a axis.
Keywords :
crystal structure , dibenzylacetone , pentan-3-one , 5-bromothiophene-2-carbaldehyde , Claisen–Schmidt
Journal title :
Acta Crystallographica Section E: Crystallographic Communications