Theoretical and experimental investigation of 2-((4-(hydroxymethyl)phenyl)(pyrrolidin-1-yl)methyl)phenol: synthesis, spectroscopic (FTIR, UV, NMR) studies, and NLO analysis

Abstract

A 2-((4-(hydroxymethyl)phenyl)(pyrrolidin-1-yl)methyl)phenol molecule is a biologically important alkylaminophenol compound. In the study, this new alkylaminophenol compound is synthesized by the Petasis reaction. The structural analysis of the molecule is performed by FTIR, 1H, 13C NMR, and UV-Vis spectrometry and supported by the computational spectral studies. The structural properties and quantum chemical calculations are carried out using the density functional theory (DFT) at the B3LYP and B3PW91 level with a 6-311++G(d,p) basis set. The NMR data are calculated by means of the GIAO method; the TD—DFT method is used for UV-Vis spectroscopy. In addition, the electronic and structural properties (bond lengths, dihedral and bond angles), HOMO and LUMO energies, NLO analysis, thermodynamic parameters (rotation constants, entropy, thermal energy, thermal capacity), vibrational frequencies, electrostatic potential (MEP), excitation energies, Mulliken atomic charges, and oscillator strengths are investigated. The results show that the molecular properties of alkylaminophenol compounds are theoretically and experimentally compatible.