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Computational Analysis of a Series of Chlorinated Chalcone Derivatives

  1. 1 Mathematics, Natural, and Health Sciences Division, University of Hawai’i—West O’ahu, Kapolei, HI, US
Computational Chemistry·Volume 07, Issue 4·Pages 106–120·Published 15 October 2019·DOI10.4236/cc.2019.74008
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Abstract

A systematic conceptual density functional theory (DFT) analysis was performed on a series of chlorinated chalcones to study the effect of electron distribution on antimicrobial activity. In our previous work, a series of 16 chlorinated chalcones were synthesized to determine the antimicrobial effects of varying the location of the halogen substituent on each aromatic ring of the chalcone. Herein is reported a DFT investigation of those 16 chalcones and a comparison of quantum chemical properties to their antimicrobial activity. DFT global chemical reactivity descriptors (chemical hardness/softness, chemical potential/electronegativity, and electrophilicity) and local reactivity descriptors (Fukui functions and dual descriptor) were calculated for all compounds using Spartan’18 software. All calculations were carried out at the B3LYP/6-31G* level of theory. Reactivity analysis of the Fukui dual descriptor calculations reveals sites of nucleophilic and electrophilic attack. These in-silico results provide a foundation for further synthetic optimization of the chalcone skeleton to serve as novel antimicrobial agents.

KeywordsDensity Functional TheoryComputational AnalysisIn-SilicoChalcone
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