IBIMOL   23987
INSTITUTO DE BIOQUIMICA Y MEDICINA MOLECULAR PROFESOR ALBERTO BOVERIS
Unidad Ejecutora - UE
artículos
Título:
Electronic structure and conformational properties of 1H-indole-3-acetic acid
Autor/es:
MARIA C. PEREZ SCHMIT; ALICIA H. JUBERT; ARTURO A. VITALE; LOBAYAN ROSANA
Revista:
JOURNAL OF MOLECULAR MODELING - (Print)
Editorial:
SPRINGER
Referencias:
Año: 2010 vol. 16 p. 1 - 13
ISSN:
1610-2940
Resumen:
The conformational space of 1H-Indole-3-Acetic Acid (IAA) was scanned using molecular dynamics at semiempirical level, and complemented with functional density calculations at B3LYP/6-31G** level, 14 conformers of lowest energy were obtained. Electronic distributions were analyzed at a higher calculation level, thus improving the basis set (B3LYP/6-311++G**). A topological
study based on Baders theory (AIM: atoms in molecules) and natural bond orbital (NBO) framework
performed with the aim to analyze the stability and reactivity of the conformers allowed the understanding of electronic aspects relevant in the study of the antioxidant properties of IAA. Intramolecular hydrogen bonds were found and were characterized as blue-shifting hydrogen
bonding interactions. Furthermore, molecular electrostatic potential maps (MEPs) were obtained and analyzed in the light of AIM and NBO results, thus showing subtle but essential features related not only to reactivity but also with intramolecular weak interactions, charge delocalization and
structure stabilization.