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 space group (Z' = 1) and its packing shows a supramolecular motif in a classical 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
Highlights
Solid-state characterization of biologically active compounds plays an important role in all areas of pharmaceutical and material sciences [1,2,3]
Considering the Triacetoxybenzoic acid (TABA) functionalities and their potential co-crystallization applications, we report the synthesis, crystallization and solid-state investigation of the anhydrous forms of TABA
The 3,4,5-triacetoxybenzoic acid (TABA) molecules is a Gallic acid (GA) derivative that exhibits multifunctional groups represented by carboxylic acid, phenol and ketone (Fig 1) which makes the molecule a strong hydrogen bond acceptor
Summary
Solid-state characterization of biologically active compounds plays an important role in all areas of pharmaceutical and material sciences [1,2,3]. The 3,4,5-triacetoxibenzoic acid, TABA (Fig 1), is a stable molecular form of the GA since all hydroxyl groups are protected as acetates, are less reactive [20, 21] This structural modification of GA gives to compound an increase in the effectiveness of the antifungal activity [22]. Considering the TABA functionalities and their potential co-crystallization applications, we report the synthesis, crystallization and solid-state investigation of the anhydrous forms of TABA In this investigation we use a combination of Single Crystal X-ray Diffraction, Infrared spectroscopy, Differential Scanning Calorimetry (DSC), Thermogravimetric (TGA), Hot Stage Microscopy techniques and DFT calculations to solid-state characterization of compound. The vibrational spectroscopy in the infrared region was recorded on a FT-IR Bomem Michelson 102 spectrometer in the 4000–250 cm-1 region using KBr pellets
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