Abstract
AbstractIn this study, the structure of 4-[4-(diethylamino)-benzylideneamino]-5-benzyl-2H-1,2,4-triazol-3(4H)-one (DBT) was examined through spectroscopic and theoretical analyses. In this respect, the geometrical, vibrational frequency,1H and13C-nuclear magnetic resonance (NMR) chemical shifts, thermodynamic, hyperpolarizability, and electronic properties including the highest occupied molecular orbital–lowest unoccupied molecular orbital (HOMO–LUMO) energies of DBT as a potential non-linear optical (NLO) material were investigated using density functional theory at the B3LYP level with the 6-311G basis set.1H and13C-NMR chemical shifts of DBT with the gauge-invariant atomic orbital and continuous set of gauge transformation methods (in the solvents) were estimated, and the computed chemical shift values displayed excellent alignment with observed ones. Time-dependent density-functional theory (TD-DFT) calculations with the integral equation formalism polarizable continuum model within various solvents and gas phases in the ground state were used to evaluate UV-vis absorption and fluorescence emission wavelengths. Thermodynamic parameters including enthalpy, heat capacity, and entropy for DBT were also calculated at various temperatures. Moreover, calculations of the NLO were carried out to obtain the title compound’s electric dipole moment and polarizability properties. To illustrate the effect of the theoretical method on the spectroscopic and structural properties of DBT, experimental data of structural and spectroscopic parameters were used. The correlational analysis results were observed to indicate a strong relationship between the experimental and theoretical results.
Highlights
In this study, the structure of 4-[4-(diethylamino)benzylideneamino]-5-benzyl-2H-1,2,4-triazol-3(4H)-one (DBT) was examined through spectroscopic and theoretical analyses
The 13C-nuclear magnetic resonance (NMR) chemical shift values for these carbon atoms (C1 and C3 bound to nitrogen atoms in the triazole ring) were recorded as 154.07 (DMSO), 152.94 (CCl4), and 153.47 ppm (CHCl3) with the gauge-invariant atomic orbital (GIAO) approach and 154.21 (DMSO), 153.39 (CCl4), and 153.77 ppm (CHCl3) with the continuous set of gauge transformation (CSGT) approach, respectively
The 13CNMR chemical shift values for these carbon atoms (C10 and C12) which bound to other nitrogen atoms in the compound were found to be 44.47 ppm, while these values of the carbons mentioned above in DMSO, CCl4, and chloroform were observed to be 60.65 (DMSO), 60.72 (CCl4), and 60.69 ppm (CHCl3) with the GIAO approach and 60.62 (DMSO), 60.68 (CCl4), and 60.65 ppm (CHCl3) with the CSGT approach, respectively
Summary
1,2,4-Triazole and its heterocyclic derivatives have drawn much attention in recent years on account of their structural properties such as ease of accessibility and good coordination diversity, the existence of π-conjugated heterocyclic system possessing good coordination abilities, the existence of nitrogen atoms as receptors of hydrogen bonds along with aromatic systems that contribute to π–π stacking leading to a variety of secondary non-covalent interactions [1,2,3,4,5,6,7,8] Their wide range of biological uses, such as the broad spectrum of biological activity, materials with optoelectronic properties, electrochemical applications, and possible energetic materials, have generated substantial interest in these compounds [9,10,11,12]. Mulliken atomic charges, thermodynamic characteristics (i.e., enthalpy, entropy, and thermal capacity) at various temperatures, and NLO properties (i.e., the first hyperpolarizability and polarizability) of DBT were examined
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
