Vol. 3, 2018

Original research papers

Other topics


Vesna Dimova, Mirjana S. Jankulovska, Milena Jankulovska

Pages: 231–235

DOI: 10.21175/RadProc.2018.48

The molecular conformations and electronic properties of a set of five N1-(o/p-substituted phenyl)aminomethyl-1,2,4-triazole derivatives (PhAMT) were investigated by two semiempirical methods: AM1 and PM3. Characteristic bond lengths (N1-C2, C2-H6, C2-N3, N3-N4, N4-C5, C5-H7 and N1 - C5), angles (N1-C2-N3, C2-N3-N4, N3-N4-C5, N4-C5-N1 and C5-N1-C2) and atomic charges (N1, C2, N3, N4, C5, H6 and H7) for 1,2,4-triazole core were calculated and discussed in accordance with literature data for similar 1,2,4-triazole compounds. The EHOMO and ELUMO values, total energies, the heats of formation and dipole moments values were calculated, as well. The discussion was performed in accordance with the type and position of a substituent present in the aromatic core.

  1. S. Maddila et al., “1,2,4-Triazoles: A Review of Synthetic Approaches and the Biological Activity,” Lett. Organic Chem., vol. 10, no. 10, pp. 693 – 714, 2013.
    DOI: 10.2174/157017861010131126115448
  2. K. Ali et al., “Short review on 1, 2, 4-Triazole with various pharmacological activity,” SD Int. J. Pharm. Sci., vol. 1, no. 1, pp. 14 – 22, Jan. 2018.
    Retrieved from: http://www.sdijps.com/rc_images/sdijps1_1_14_22pdf.pdf;
    Retrieved on: Jul. 23, 2018
  3. R. Singh et al., “Design and Synthesis of New Bioactive 1,2,4-Triazoles, Potential Antitubercular and Antimicrobial Agents,” Indian J. Pharm. Sci.,vol. 80, no. 1, pp. 36 – 45, 2018.
    DOI: 10.4172/pharmaceutical-sciences.1000328
  4. N. Jaiprakash et al., “Synthesis, Antifungal Activity, and Docking Study of Some New 1,2,4-triazole Analogs,” Chem. Biol. Drug Design, vol. 78, no. 5, pp. 800 – 809, Nov. 2011.
    DOI: 10.1111/j.1747-0285.2011.01178.x
  5. H. Sadeghpour et al., “Design, Synthesis, and Biological Activity of New Triazole and Nitro-Triazole Derivatives as Antifungal Agents,” Molecules, vol. 22, no. 7, 1150, Jul. 2017.
    DOI: org/10.3390/molecules22071150
  6. A. Usman Rasheed et al., “ADME/T Prediction, Molecular Docking, and Biological Screening of 1,2,4-Triazoles as Potential Antifungal Agents,” J. Appl. Bioinform. Computat. Biol., vol. 7, no. 1, Jan. 2018.
    DOI: 10.4172/2329-9533.1000144
  7. M. Lazarevi et al., “Synthesis of some N 1 – Aryl/heteroarylaminomethyl/ethyl-1,2,4-triazoles and their antibacterial and antifungal activities,” Heterocycl. Commun., vol. 7, no. 1, pp. 577 – 582,
    May 2001.
    DOI: org/10.1515/HC.2001.7.6.577
  8. HyperChem(TM) Professional 7.51, Hypercube, Inc., Gainesville (FL), USA, 2018.
    Retrieved from: http://www.hyper.com/;
    Retrieved on: Jul. 23, 2018
  9. M. J. S. Dewar et al., “Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model,” J. Am. Chem. Soc., vol. 107, no. 13, pp. 3902 – 3909, Jun, 1985.
    DOI: 10.1021/ja00299a024
  10. J. J. P. Stewart, “Optimization of parameters for semiempirical methods I. Method,” J. Computat. Chem., vol. 10, no. 2, pp. 209 – 220, Mar. 1989.
    DOI: org/10.1002/jcc.540100208
  11. R. D. Johnson III, NIST Computational Chemistry Comparison and Benchmark Database: NIST Standard Reference Database Number 101, Release 19, National Institute of Standard and Technology, Gaithersburg (MD), USA, 2018.
    Retrieved from: http://cccbdb.nist.gov/
    Retrieved on: Dec. 12, 2017
  12. L. Xiao-Hong et al., “Quantum chemical studies on the structure and performance properties of 2,5,2`-triazido-1,1`-azo-1,3,4-triazole,” Indian J. Chem. Sec. A, vol. 53A, no. 3, pp. 281 – 287, Mar. 2014.
    Retrieved from: http://nopr.niscair.res.in/handle/123456789/27394;
    Retrieved on: Apr. 23, 2018
  13. J. L. Escobar-Valderrama et al., “Crystal, molecular and electronic structure of 1-H-3-methyl-4-amine-5-thione-1,2,4-triazol,” Can. J. Chem., vol. 67, no. 2, pp. 198 – 201, Feb. 1989.
    DOI: org/10.1139/v89-033
  14. I. A. Adejoro et al, “Quantum Descriptors and Corrosion Inhibition Potentials of Amodaquine and Nivaquine,” Chem. Sci. J., vol. 8, no. 1, 149, Jan. 2017.
    DOI: 10.4172/2150-3494.1000149
  15. A. A. Ikizler et al., “A Quantum-Chemical Investigation on 5,5`-BI(1H-1.2,4-Triazole),” Turk. J. of Chem., vol. 21, no. 4, pp. 353 – 362, 1997.
    Retrieved from: http://journals.tubitak.gov.tr/chem/issues/kim-97-21-4/kim-21-4-16-97056.pdf;
    Retrieved on: Apr. 23, 2018
  16. Z. Rui-Zhou et al., “Theoretical studies on a series of 1,2,4-triazoles derivatives as potential high energy density compounds”, J. Chem. Sci., vol. 124, no. 5, pp. 995 – 1006, Sep. 2012.
    DOI: 10.1007/s12039-012-0304-7