Abstract:

2-(N-(2-hydroxyphenyl)-2-propylpentanamide) [OH-VPA], a histone deacetylase inhibitor (HDCA) with antitumor activity, is a new aryl valproic acid (VPA) derivative. In this work, structural, spectroscopic and electronic properties of OH-VPA were investigated by theoretical calculations. Optimized molecular geometry and harmonic vibrational frequencies of OH-VPA were calculated using the Density Functional Theory (DFT) B3LYP method with 6- 311++G(d,p) basis set. UV-Vis. electronic absorption parameters, HOMO-LUMO gap and molecular electrostatic potential (MEP) surface analyses and chemical reactivity descriptors of OH-VPA were performed to understand the reactivity of the molecule by the TD-DFT approach. Moreover, the values of the chemical shifts of the 13C NMR and 1H NMR were computed using the gauge independent atomic orbital (GIAO) method applying the same method and the same basis set as used in geometry optimization. The mean polarizability (α), the anisotropy of the polarizability (Δα) and the mean first-order hyperpolarizability (β) were calculated by using the finite field method. The high β values (2.144x10-30 esu) indicate that the studied compound may be a good candidate in the development of NLO materials. The structural parameters, vibrational wavenumbers, NMR chemical shifts of the molecule which are calculated theoretically are a good agreement with the experimental results obtained from the literature.

Keywords: