Single crystal, Hirshfeld surface and theoretical analysis of methyl 4-hydroxybenzoate, a common cosmetic, drug and food preservative—Experiment versus theory

Abstract
Methyl 4-hydroxybenzoate, commonly known as methyl paraben, is an anti-microbial agent used in cosmetics and personal-care products, and as a food preservative. In this study, the single crystal X-ray structure of methyl 4-hydroxybenzoate was determined at 120 K. The crystal structure comprises three methyl 4-hydroxybenzoate molecules condensed to a 3D framework via extensive intermolecular hydrogen bonding. Hirshfeld surface analysis was performed to determine the intermolecular interactions and the crystal packing. In addition, computational calculations of methyl 4-hydroxybenzoate were obtained using the Gaussian 09W program, and by quantum mechanical methods, Hartree Fock (HF) and Density Functional Theory (DFT) with the 6–311G(d,p) basis set. The experimental FT-IR spectrum strongly correlated with the computed vibrational spectra (R2 = 0.995). The energies of the frontier orbitals, HOMO and LUMO, were used to calculate the chemical quantum parameters. The lower band gap value (ΔE) indicates the molecular determinants underlying the known pharmaceutical activity of the molecule.

Citation
Sharfalddin, A., Davaasuren, B., Emwas, A.-H., Jaremko, M., Jaremko, Ł., & Hussien, M. (2020). Single crystal, Hirshfeld surface and theoretical analysis of methyl 4-hydroxybenzoate, a common cosmetic, drug and food preservative—Experiment versus theory. PLOS ONE, 15(10), e0239200. doi:10.1371/journal.pone.0239200

Acknowledgements
We thank King Abdul Aziz University for using their facilities and also thank King Abdullah University of Science and Technology (KAUST) for their support.
The author(s) received no specific funding for this work.

Publisher
Public Library of Science (PLoS)

Journal
PLOS ONE

DOI
10.1371/journal.pone.0239200

Additional Links
https://dx.plos.org/10.1371/journal.pone.0239200

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