Structure-property relationship of 3-(N-phthalimidomethyl)-4-amino-1,2,4-triazole-5-thione: A structural, spectroscopic and DFT study

The title molecule, 3-(N-phthalimidomethyl)-4-amino-1,2,4-triazole-5-thione (C11H9N5O2S), was synthesized by the fusion of N-Phthaloylglycine and thiocarbohydrazide at 145 degrees C. In this study, we have investigated the crystal structure, photophysical properties as well as the relation between the molecular structure and nonlinear optical properties of 2-(4-Amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-ylmethyl)isoindoline-1,3-dione. For this purpose, the molecular structure, vibration spectrum, electronic absorption spectrum, H-1 and C-13 NMR spectra have been evaluated by both of the experimental techniques and density functional theory method. A detailed assignment of vibrational bands has been performed on the basis of potential energy distribution analysis. Additionally, UV-Vis spectrum was recorded in different solvents in order to examine the solvent effect on the electronic absorption spectrum. NBO analysis has been carried out to investigate intra-molecular charge transfer interactions. Finally, nonlinear optical properties of the title compound have been investigated by using M062X level of density functional theory. (C) 2016 Elsevier B.V. All rights reserved