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Zeitschrift für Physikalische Chemie

International journal of research in physical chemistry and chemical physics

Editor-in-Chief: Rademann, Klaus

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Structural, Vibrational and UV/Vis Studies of Adamantane-Containing Triazole Thiones by Spectral, DFT and Multi-reference ab initio Methods

Maksim Shundalau
  • Corresponding author
  • Faculty of Physics, Belarusian State University, 4 Nezaležnaści Ave., 220030 Minsk, Belarus
  • A.N. Sevchenko Institute of Applied Physical Problems at Belarusian State University, 7 Kurčatau Str., 220108 Minsk, Belarus
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  • Other articles by this author:
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/ Yuliya L. Mindarava / Anna S. Matsukovich
  • B.I. Stepanov Institute of Physics, National Academy of Science of Belarus, 68 Nezaležnaści Ave., 220072 Minsk, Belarus
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/ Sergey V. Gaponenko
  • Faculty of Physics, Belarusian State University, 4 Nezaležnaści Ave., 220030 Minsk, Belarus
  • B.I. Stepanov Institute of Physics, National Academy of Science of Belarus, 68 Nezaležnaści Ave., 220072 Minsk, Belarus
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/ Ali A. El-Emam
  • Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansour 35516, Egypt
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/ Hamad N. Alkahtani
  • Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
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Published Online: 2019-03-28 | DOI: https://doi.org/10.1515/zpch-2018-1271


The Fourier transform infrared and Raman spectra of two adamantane-containing triazole thiones, namely 3-(adamantan-1-yl)-1-[(4-benzylpiperazin-1-yl)methyl]-4-phenyl-1H-1,2,4-triazole-5(4H)-thione and 3-(adamantan-1-yl)-4-phenyl-1-[(4-phenylpiperazin-1-yl)methyl]-1H-1,2,4-triazole-5(4H)-thione, were examined in the ranges of 3200–650 cm−1 and 3200–150 cm−1, respectively. The density functional theory calculations were performed for the geometric structures and vibrational spectra for the title molecules. The accurate equilibrium geometry structures of the molecules were determined on the basis of full geometry optimization at the B3LYP/cc-pVDZ level of the theory. The IR and Raman vibrational spectra were calculated and compared with the experimental ones. The experimental vibrational FT-IR and Raman spectra were interpreted. Based on the structure of the molecules the biological activity indices were predicted. It is established that compounds under consideration are very likely to exhibit the analgesic activities. The UV/Vis spectra of solution of the compounds in ethanol were measured in the range of 450–200 nm. The UV/Vis spectra simulations at the Time-Dependent DFT and Multi-Reference Perturbation Theory levels of theory demonstrate unsuitability of the TDDFT for description of the experimental spectra of the title molecules. It is highly probable that this is a consequence of the intramolecular charge transfer. In contrast, the MRPT results are in a good agreement with the experimental spectra.

This article offers supplementary material which is provided at the end of the article.

Keywords: 3-(adamantan-1-yl)-1-[(4-benzylpiperazin-1-yl)methyl]-4-phenyl-1H-1,2,4-triazole-5(4H)-thione; 3-(adamantan-1-yl)-4-phenyl-1-[(4-phenylpiperazin-1-yl)methyl]-1H-1,2,4-triazole-5(4H)-thione; biological activity; multi-reference perturbation theory calculations; UV/Vis spectrum; vibrational spectra


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About the article

Received: 2018-07-31

Accepted: 2019-02-25

Published Online: 2019-03-28

Funding Source: Belarusian Republican Foundation for Fundamental Research

Award identifier / Grant number: Nr. F18MS-046

This work has been supported by the Belarusian Republican Foundation for Fundamental Research (Funder Id: http://dx.doi.org/10.13039/100007595, Nr. F18MS-046). Ali A. El-Emam and Hamad M. Alkahtani also extend their appreciation to the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University for funding this research.

Citation Information: Zeitschrift für Physikalische Chemie, 20181271, ISSN (Online) 2196-7156, ISSN (Print) 0942-9352, DOI: https://doi.org/10.1515/zpch-2018-1271.

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