Conformational studies of 2-(4-bromophenyl)-2-oxoethyl benzoates

Kumar, C. S. C. and Chia, T. S. and Chandraju, S. and Ooi, C. W. and Quah, C. K. and Fun, H. K. (2014) Conformational studies of 2-(4-bromophenyl)-2-oxoethyl benzoates. Zeitschrift Fur Kristallographie-Crystalline Materials, 229 (4). pp. 328-342.

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Official URL: https://doi.org/10.1515/zkri-2013-1709

Abstract

Phenacyl benzoates possess commercial importance due to their various applications in the fields of synthetic and photochemistry, such as photosensitive blocking groups owing to their ease of cleavage under mild conditions. In the present study, a series of ten new 2-(4bromopheny1)-2-oxoethyl benzoates 2(a -j), with the general formula Br(C6H4)COCH2OCO(C6H(5-n),X-n), X = Cl, NO2 or NH2, and n =1 or 2, have been synthesized by reacting 4-bromophenacyl bromide with various substituted benzoic acids using potassium carbonate in DMF medium at room temperature. These reactions proceeded with ease under mild conditions producing high purity products in good yield. Each product was characterized by mass spectra, elemental analysis and melting points, its 3D structure was confirmed by single-crystal X-ray diffraction studies. The X-ray 3D structures showed the flexibility of the C(=0)-O- C C(=0) connecting bridge in which 7 out of 10 compounds tend to form a torsion angle in the range of 70 to 91, whereas the rest are slightly twisted with a torsion angles of 160, 163, 176 and 178. Their molecular conformations are in good agreement with another 22 related structures. These synthesized compounds were screened for their abilities for DPPH radical scavenging and ferric reducing anti-oxidant power. The results indicate that these compounds displayed mild anti-oxidant ability when compared to the standard anti-oxidant BHT.

Item Type: Article
Uncontrolled Keywords: crystal structure; stability; conformation; radical scavenging; substituent
Subjects: D Physical Science > Sugar Technology
Divisions: PG Centre Mandya > Sugar Technology
Depositing User: Arshiya Kousar
Date Deposited: 07 Sep 2019 05:39
Last Modified: 18 Sep 2019 09:39
URI: http://eprints.uni-mysore.ac.in/id/eprint/7714

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