Abstract
Two crystal structures of chalcones, or 1,3-di-aryl-prop-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-methyl-chalcone [systematic name: 1-(2-bromo-phen-yl)-3-(4-methyl-phen-yl)prop-2-en-1-one], C16H13BrO, and 3'-cyano-4-methyl-chalcone {systematic name: 2-[3-(4-methyl-phen-yl)prop-2-eno-yl]benzo-nitrile}, C17H13NO. Both chalcones meaningfully add to the large dataset of chalcone structures. The crystal structure of 3'-cyano-4-methyl-chalcone exhibits close contacts with the cyano nitro-gen that do not appear in previously reported disubstituted cyano-chalcones, namely inter-actions between the cyano nitro-gen atom and a ring hydrogen atom as well as a methyl hydrogen atom. The structure of 3'-bromo-4-methyl-chalcone exhibits a type I halogen bond, similar to that found in a previously reported structure for 4-bromo-3'-methyl-chalcone.
Highlights
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 crystal structure of 30-cyano4-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
This paper compares the structure and packing of two newly crystallized chalcone molecules, 30-cyano-4-methylchalcone [Sm6p] or m0CNpCH3 and 30-bromo-4-methylchalcone [Dm6p] or m0BrpCH3, where Sm6p and Dm6p are internal codes tied to a large, long-term project
Summary
Chalcones are organic molecules commonly found in nature consisting of two phenyl rings connected by an , -unsaturated ketone, or enone. Interest in chalcone molecules has risen because of their potential pharmaceutical properties, electronic properties, and straightforward synthesis via a Claisen–Schmidt condensation between a benzaldehyde and acetophenone (Zhuang et al, 2017). Some chalcones have been shown to be fluorescent, making them potential probes for mechanistic investigations and imaging (Lee et al, 2012). This paper compares the structure and packing of two newly crystallized chalcone molecules, 30-cyano-4-methylchalcone [Sm6p] or m0CNpCH3 and 30-bromo-4-methylchalcone [Dm6p] or m0BrpCH3, where Sm6p and Dm6p are internal codes tied to a large, long-term project. Substitution on the 1-Ring has been utilized to further understand the packing and structure of chalcone crystals based upon their ring substituents
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