Structural and Theoretical Investigation of Anhydrous 3,4,5-Triacetoxybenzoic Acid

Author(s)

Carvalho, Jr., Paulo S. ^{[1, 2]} ; Almeida, Leonardo R. ^{[1, 2]} ; Araujo Neto, Joao H. ^{[3, 2]} ; Medina, Ana Carolina Q. D. ^[1] ; Menezes, Antonio C. S. ^[2] ; Sousa, Jose. F. ^[2] ; Oliveira, Solemar S. ^[2] ; Camargo, Ademir J. ^[2] ; Napolitano, Hamilton B. ^[2]

Affiliation

^[1] Univ Sao Paulo, Inst Fis Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil

^[2] Univ Estadual Goias, Ciencias Exatas & Tecnol, BR-75132400 Anapolis, Go - Brazil

^[3] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP - Brazil

• Document type: Journal article
• Source: PLoS One; v. 11, n. 6 JUN 29 2016.
• Web of Science Citations: 1

Abstract

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 triclinic P (1) over bar space group (Z' = 1) and its packing shows a supramolecular motif in a classical R-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 (AU)

• FAPESP's process: 12/05616-7 - Solid-state characterization of anticonvulsant and antidepressant phamaceutical compounds: Design of new crystal forms.
• Grantee: Paulo de Sousa Carvalho Júnior
• Support Opportunities: Scholarships in Brazil - Doctorate