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

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)e0239200
JournalPLOS ONE
Volume15
Issue number10
DOIs
StatePublished - Oct 6 2020

Bibliographical note

KAUST Repository Item: Exported on 2020-10-08
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.

Fingerprint

Dive into the research topics of 'Single crystal, Hirshfeld surface and theoretical analysis of methyl 4-hydroxybenzoate, a common cosmetic, drug and food preservative—Experiment versus theory'. Together they form a unique fingerprint.

Cite this