Open AccessStructural and Theoretical Investigation of Anhydrous 3,4,5-Triacetoxybenzoic Acid
Author(s) -
Paulo S. Carvalho,
Leonardo R. Almeida,
José Peduti Neto,
Ana Carolina Q. D. Medina,
Antônio Carlos Severo Menezes,
José E. F. Sousa,
Silvia Sanielle Costa de Oliveira,
Ademir J. Camargo,
Hamilton B. Napolitano
Publication year - 2016
Publication title -
plos one
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.99
H-Index - 332
ISSN - 1932-6203
DOI - 10.1371/journal.pone.0158029
Subject(s) - triclinic crystal system , anhydrous , conformational isomerism , supramolecular chemistry , crystallography , fourier transform infrared spectroscopy , infrared spectroscopy , infrared , thermal stability , chemistry , crystal structure , molecule , density functional theory , computational chemistry , materials science , physics , organic chemistry , optics
A comprehensive investigation of anhydrous form of 3,4,5-Triacetoxybenzoic acid (TABA) is reported. Single crystal X-ray diffraction, Thermal analysis, Fourier Transform Infrared spectroscopy (FTIR) and DFT calculations were applied for TABA characterization. This anhydrous phase crystallizes in the triclinicP 1 ¯space group (Z' = 1) and its packing shows a supramolecular motif in a classicalR 2 2 ( 4 )ring formed by acid-acid groups association. The phase stability is accounted in terms of supramolecular architecture and its thermal behaviour. Conformation search at B3LYP/6-311++G(2d,p) level of theory shows the existence of three stable conformers and the most stable conformation was found experimentally. The reactivity of TABA was investigated using the molecular orbital theory and molecular electrostatic potential. The calculation results were used to simulate the infrared spectrum. There is a good agreement between calculated and experimental IR spectrum, which allowed the assignment of the normal vibrational modes