title: Electronic structure and conformational properties of 1H-indole-3-acetic acid.
abstract: 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 Bader's theory (
  
  
  OBJECTIVE
  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.
authors: Facultad de Ingeniería, Universidad de la Cuenca del Plata, Corrientes, Argentina.
authors: María C Pérez
authors: MC
authors: Schmit
authors: Alicia H
authors: AH
authors: Jubert
authors: Arturo
authors: A
authors: Vitale
authors: Rosana M
authors: RM
authors: Lobayan
mesh_terms: D000465:Algorithms; D004563:Electrochemistry; D004583:Electrons; D006860:Hydrogen Bonding; D007210:Indoleacetic Acids / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013499:Surface Properties; D013816:Thermodynamics
chemical_list: D007210:Indoleacetic Acids; C030737:indoleacetic acid