Author/Authors :
Battaglia, Zachary O. Department of Chemistry & Biochemistry - Gonzaga University, USA , Kersten, Jordan T. Department of Chemistry & Biochemistry - Gonzaga University, USA , Nicol, Elise M. Department of Chemistry & Biochemistry - Gonzaga University, USA , Whitworth, Paloma Department of Chemistry & Biochemistry - Gonzaga University, USA , Wheeler, Kraig A. Department of Chemistry - Whitworth University, USA , Hall, Charlie L. School of Chemistry - University of Bristol, England , Potticary, Jason School of Chemistry - University of Bristol, England , Hamilton, Victoria School of Chemistry - University of Bristol, England , Hall, Simon R. School of Chemistry - University of Bristol, England , D'Ambruoso, Gemma D. Department of Chemistry & Biochemistry - Gonzaga University, USA , Matsumoto, Masaomi Department of Chemistry & Biochemistry - Gonzaga University, USA , Warren, Stephen D. Department of Chemistry & Biochemistry - Gonzaga University, USA , Cremeens, Matthew E. Department of Chemistry & Biochemistry - Gonzaga University, USA
Abstract :
Two crystal structures of chalcones, or 1,3-diarylprop-2-en-1-ones, are presented; both contain a methyl substitution on the 3-Ring, but differ on the 1-Ring, bromo versus cyano. The compounds are 3′-bromo-4-methylchalcone [systematic name: 1-(2-bromophenyl)-3-(4-methylphenyl)prop-2-en-1-one], C16H13BrO, and 3′-cyano-4-methylchalcone {systematic name: 2-[3-(4-methylphenyl)prop-2-enoyl]benzonitrile}, C17H13NO. Both chalcones meaningfully add to the large dataset of chalcone structures. The crystal structure of 3′-cyano-4-methylchalcone exhibits close contacts with the cyano nitrogen that do not appear in previously reported disubstituted cyanochalcones, namely interactions between the cyano nitrogen atom and a ring hydrogen atom as well as a methyl hydrogen atom. The structure of 3′-bromo-4-methylchalcone exhibits a type I halogen bond, similar to that found in a previously reported structure for 4-bromo-3′-methylchalcone.
Keywords :
crystal structure , chalcone , bromo , cyano , halogen bond , π stacking , edge-to-face
