Structural, spectroscopic and O-H•••O hydrogen bonding interaction on monomer and dimer form of hydroxy phenoxy acetic acid derivatives by experimental and computational techniques

Spectral analysis of commercially available cardiovascular drug 4-(hydroxyphenoxy)acetic acid (HPAA) was performed by experimental and theoretical IR, Raman, UV-Vis and NMR techniques.The optimized geometry, wavenumber and intensity of the vibrational bands of a monomer and dimer form of hydroxyphenoxy acetic acid and its related compounds were obtained by the density functional theory (B3LYP) using 6-311 + G(D,P) basis set to reveal the cardiovascular activity of the compound. The most stable conformation of the title compound was carried out by potential energy scan analysis to identify the active sites of the molecule. The natural bond orbital analysis was performed to analyze the activity of the compound. The HOMO-LUMO and MEP analyses were carried out to identify the active part of the molecule. This work was extended to calculate the binding energy and cardiovascular active part of the title compound with suitable protein by Autodock software. The molecular descriptors obtained by the DFT method was used for QSAR model and predicting the cytotoxicity of HPAA. Fingerprint plots and Hirshfeld surfaces were used to locate and analyze the molecular surface and bonding interactions and cardiovascular activity in various methodologies utilized in the establishment of the relative energies. 4-(hydroxyphenoxy)acetic acid was screened for its cardiovascular activity. (C) 2019 Elsevier B.V. All rights reserved.