Effect of OH substitution in 3-benzylchroman-4- ones: crystallographic, CSD, DFT, FTIR, Hirshfeld surface, and energy framework analysis

Salam, Abdul Ajees Abdul and Shilpa, T and Bankapur, Aseefhali and Sinha, Rajeev K and Chidangil, Santhosh (2021) Effect of OH substitution in 3-benzylchroman-4- ones: crystallographic, CSD, DFT, FTIR, Hirshfeld surface, and energy framework analysis. RSC Advances, 11 (33). pp. 20123-20136. ISSN 10795-10800

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Abstract

3-Benzylchroman-4-ones (homoisoflavanones) are oxygen-containing heterocycles with a sixteen-carbon skeleton. They belong to the class of naturally occurring polyphenolic flavonoids with limited occurrence in nature and possess anti-inflammatory, antibacterial, antihistaminic, antimutagenic, antiviral, and angioprotective properties. Recently, we reported the synthesis and anticancer activity studies of fifteen 3-benzylchroman-4-one molecules, and most of them were proven to be effective against BT549 and HeLa cells. In this work, we report the single-crystal X-ray crystallographic studies of two molecules 3- [(2-hydroxyphenyl)methyl]-3,4-dihydro-2H-1-benzopyran-4-one and 3-[(2,4-dimethoxyphenyl)methyl]- 3,4-dihydro-2H-1-benzopyran-4-one. The single crystals were grown using a novel laser-induced crystallization technique. We observed that the 3-benzylchroman-4-one derivative bearing OH] substitution at the 20 position adopted different conformation due to formation of dimers through O–H/O, and C–H/O intermolecular hydrogen bondings. The role of OH substitution in the aforementioned conformational changes was evaluated using density functional theory (DFT), Hirshfeld surface, energy framework and FTIR spectroscopy analysis. In addition, we have carried out a Cambridge Structural Database (CSD) study to understand the conformational changes using five analogue structures. X-ray crystallographic, computational, and spectroscopic studies of 3-benzylchroman-4-ones provided an insight into the role of substitution at benzyl moieties in stabilizing the three-dimensional (3D) structures.

Item Type: Article
Subjects: Departments at MU > Atomic Molecular Physics
Depositing User: KMC Library
Date Deposited: 08 Sep 2021 10:35
Last Modified: 08 Sep 2021 10:35
URI: http://eprints.manipal.edu/id/eprint/157286

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