Crystal and molecular structure of 2-methyl-1,4-phenylene bis(3,5-dibromobenzoate)

Abstract

The aryl diester compound, 2-methyl-1,4-phenylene bis(3,5-dibromobenzoate), C21H12Br4O4, was synthesized by esterification of methyl hydroquinone with 3,5-dibromobenzoic acid. A crystalline sample was obtained by cooling a sample of the melt (m.p. = 502 K/DSC) to room temperature. The molecular structure consists of a central benzene ring with anti-3,5-dibromobenzoate groups symmetrically attached at the 1 and 4 positions and a methyl group attached at the 2 position of the central ring. In the crystal structure (space group P\overline{1}), molecules of the title aryl diester are located on inversion centers imposing disorder of the methyl group and H atom across the central benzene ring. The crystal structure is consolidated by a network of C—H...Br hydrogen bonds in addition to weaker and offset π–π interactions involving the central benzene rings as well as the rings of the attached 3,5-dibromobenzoate groups.

Keywords

• crystal structure
• inverse vulcanization (inv)
• rasp
• steglich esterification
• dithiocarbamate (dtc) catalyst