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DFT study of structural and electronic properties of gallic acid and its anions in gas phase and in aqueous solution

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Abstract

Gallic acid, one of the naturally occurring antioxidants, has been characterized in terms of its structural and chemical properties using the density functional approach. The intramolecular interactions have been identified using natural bond orbital (NBO) analysis. The gallic acid anion and dianion have also been studied for determining the first two pK a values. Further, an investigation of the molecular orbitals reveals a dependence of the frontier molecular orbitals on external factors, viz. pH and dielectric of the medium. Consequently, the electronic spectra have been simulated in a range of solvents using steered molecular dynamics. Furthermore, the IR and NMR spectra of the neutral and the deprotonated state have been simulated. Additionally, the spectra have been experimentally recorded to validate the methodology followed. The present work also examines the variation in global and local reactivities of gallic acid under the influence of external factors. Each atom has been quantitatively assessed for its susceptibility towards nucleophilic, electrophilic, and radical attack.

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Acknowledgements

One of the authors (B.B.) thanks the Council of Scientific and Industrial Research (CSIR), New Delhi, for Senior Research Fellowship. The authors thank Delhi University’s “Scheme to Strengthen Doctoral Research by Providing Funds to Faculty.” We also thank USIC-CIF, University of Delhi, for providing facilities to acquire FT-IR and NMR data.

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  1. Computational Chemistry Laboratory, Department of Chemistry, University of Delhi, Delhi, 110007, India

    Bharti Badhani & Rita Kakkar

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  1. Bharti Badhani
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Correspondence to Rita Kakkar.

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Badhani, B., Kakkar, R. DFT study of structural and electronic properties of gallic acid and its anions in gas phase and in aqueous solution. Struct Chem 28, 1789–1802 (2017). https://doi.org/10.1007/s11224-017-0958-3

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