Structural study, coordinated normal analysis and vibrational spectra of 4-hydroxy-3-(3-methyl-2-butenyl)acetophenone

Abstract

Structural and vibrational properties of 4-hydroxy-3-(3-methyl-2-butenyl)acetophenone, isolated from Senecio nutans Sch. Bip. (Asteraceae) were studied by infrared and Raman spectroscopies in solid phase. The Density Functional Theory (DFT) method together with Pople's basis set show seven stable conformers for the compound in the gas phase and that only two conformations are probably present in the solid phase. The harmonic vibrational wavenumbers for the optimized geometry were calculated at B3LYP/6-31G and B3LYP/6-311++G levels. For a complete assignment of the vibrational spectra, DFT calculations were combined with Pulay´s Scaled Quantum Mechanics Force Field (SQMFF) methodology in order to fit the theoretical wavenumber values to the experimental ones. Then, a complete assignment of all the observed bands in the vibrational spectra was performed. The natural bond orbital (NBO) study reveals the characteristics of the electronic delocalization of the two stable structures, while the corresponding topological properties of electronic charge density were analyzed by employing Bader's Atoms in the Molecules theory (AIM).