A Theoretical and Experimental Study on Hydrogen-bonding Interactions between 4H-1,2,4-triazole-3,5-diamine and DMSO/water

Mustafa Tuğfan Bilkan

Abstract


In this paper, 4TZDA-DMSO/water complexes formed by hydrogen bonding interactions were investigated by a combined experimental and computational approach. Two conformations of 4TZDA molecule were considered. Seven hydrogen-bonded 4TZDA-DMSO/H2O complexes were characterized in terms of geometries, energies and vibrational frequencies. The optimizations and calculations were performed for the complexes by Density Functional Theory. In the experimental part, the DMSO/H2O solutions of 4TZDA were prepared and infrared spectra of the solutions were recorded. After the solvation process, significant shifts in the existing bands and new band rising were observed in the experimental spectra of 4TZDA. Following results are found from this study: 1) 4TZDA (I) is more stable than 4TZDA (II). 2) Seven 4TZDA-DMSO and 4TZDA-H2O complexes are investigated and it is seen that all nitrogen atoms of 4TZDA are hydrogen bond acceptor and all hydrogen atoms are hydrogen bond donors. 3) Aqueous complexes of 4TZDA are found to form stronger hydrogen bonds compared to DMSO complexes. 4) It is determined that the most stable structures are intermolecular interactions of lpO⋯H-N and lpN⋯H-O type for the complexes. For these interactions, h-bond lengths are calculated as 1.78 and 1.90 Å and interaction energies are -7.10 kJ/mol for 4TZDA-DMSO and -50.5 kJ/mol for 4TZDA-H2O. Because of this energy difference in the complexes, it can be said 4TZDA forms more stable complexes with water molecules compared to DMSO molecules and with this property, it is an ideal molecule for pharmacological purposes.


Keywords


4H-1,2,4-triazole-3,5-diamine; solvent effects; hydrogen bonding; DFT; FT-IR spectroscopy

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References


J.A. Vick, E.H. Herman, Cardiovascular effects of guanazole, Toxic. App. Pharm. 16, 108-119 (1970)

https://doi.org/10.1016/0041-008X(70)90167-5

M.A. Hahn, H.R. Adamson, The Disposition of the Antitumour Agent 3,5-Diamino-1,2,4-triazole (Guanazole) in Mice, Rats and Dogs, Xenbiotica, 3, 247-255 (1973)

https://doi.org/10.3109/00498257309151520

C. Dave, M.A. Paul, Y.M. Rustum, Studies on the selective toxicity of guanazole in mice, Eur. J. Cancer. 14, 33-40 (1978)

C.D. Selassie, E.J. Lie, T.A. Khwaja, Synthesis and evaluation of guanazole prodrugs as antineoplastic agents J. Pharm. Sci. 70, 1281-1283 (1981)

https://doi.org/10.1002/jps.2600701126

W. Suter, F. Romagna, DNA repair induced by various mutagens in rat hepatocyte primary cultures measured in the presence of hydroxyurea, guanazole or aphidicolin, MUTAT. RES-FUND. MOL. M. 231, 251-264 (1990)

https://doi.org/10.1016/0027-5107(90)90031-X

J.A. Ho, C.V. Pickens, M.P. Gamscik, O.M. Colvin, R.E. Ware, In vitro induction of fetal hemoglobin in human erythroid progenitor cells, Exp. Hematol. 31, 586-591 (2003)

https://doi.org/10.1016/S0301-472X(03)00086-9

X. Zhao, M.R. Rosenberg, J. Wan, S. Zeng, W. Cui, Y. Xiao, Z. Li, Z. Tu, M.G. Casarotto, W. Hu, Design and synthesis of pinanamine derivatives as anti-influenza A M2 ion channel inhibitors, Antivir. Res. 96, 91-99 (2012)

https://doi.org/10.1016/j.antiviral.2012.09.001

V.K. Kumar, G. Keresztury, T. Sundius, R.J. Xavier, Hydrogen bonding and molecular vibrations of 3,5-diamino-1,2,4-triazole, Spectrochim. Acta Part A. 61, 261-267 (2005)

https://doi.org/10.1016/j.saa.2004.03.039

L. Guennoun, J. El jastimi, F. Guédira, K. Marakchi, O.K. Kabbaj, A. El Hajji, S. Zaydoun, Molecular geometry and vibrational studies of 3,5-diamino-1,2,4-triazole using quantum chemical calculations and FT-IR and FT-Raman spectroscopies, Spectrochim. Acta Part A. 78, 347-353 (2011)

https://doi.org/10.1016/j.saa.2010.10.019

A. Ray, M. Samiran, M.R. Georgina, A novel hydroxo-bridged cyclic tetranuclear copper(II) complex using the guanazole ligand: Synthesis, crystal structure and thermal analysis, Inorg. Chem. Com. 11, 1256-1259 (2008)

https://doi.org/10.1016/j.inoche.2008.07.010

I. Matulková, I. Císarová, P. Nemec, J. Kroupa, P. Vanek, N. Tesarˇová, Organic salts of guanazole – Seeking for new materials for second harmonic generation, J. Mol. Struct. 1044, 239-247 (2013)

https://doi.org/10.1016/j.molstruc.2012.11.011

P. Cui, L. Xiaohui, Construction of two new Zn(II)-guanazole frameworks via varying organic carboxylate ligands, J. Mol. Struct., 1081, 182-186 (2015)

https://doi.org/10.1016/j.molstruc.2014.09.081

H. Zhao, D. Yanli, L. Haiping, Two new luminescent Zn(II) compounds constructed from guanazole and aromatic polycarboxylate ligands, J. Mol. Struct. 1105, 112-117 (2016)

https://doi.org/10.1016/j.molstruc.2015.10.046

G. Karpin´ska, J.C. Dobrowolksi, On tautomeric equilibria in the guanazole molecule. A DFT study, J. Mol. Struct. THEOCHEM. 853, 7-17 (2008)

https://doi.org/10.1016/j.theochem.2007.11.036

S. Miertuš, E. Scrocco, J. Tomasi, Electrostatic interaction of a solute with a continuum. A direct utilizaion of AB initio molecular potentials for the prevision of solvent effects, Chem. Phys. 55, 117-129 (1981)

https://doi.org/10.1016/0301-0104(81)85090-2

B.N. Swanson, Medical use of dimethyl sulfoxide (DMSO).Reviews in Clinical & Basic Pharmacology, Rev. Clin. Basic Pharm. 5, 1-33 (1985)

R.D. Dennington, T.A. Keith, J.M. Millam, GaussView 5, Gaussian, Inc. 2008.

Frisch, M. J. et al. Gaussian 09. Gaussian, Inc.: Wallingford, CT, 2009.

M.H. Jamróz, "Vibrational Energy Distribution Analysis" VEDA 4, Warsaw 2004.

N. Sundaraganesan, G. Elango, S. Sebastian, P. Subramani, Molecular structure, vibrational spectroscopic studies and analysis of 2-fluoro-5-methylbenzonitrile, Indian J. Pure Ap. Phy. 47, 481-490 (2009)

http://hdl.handle.net/123456789/5056.

Boys SF, Bernardi F. The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Mol. Phys. 19, 553–559 (1970)

M.T. Bilkan, Quantum chemical studies on solvent effects, ligand–water complexes and dimer structure of 2,2ʹ-dipyridylamine, Phys. Chem. Liq. 57, 100-116 (2019)

https://doi.org/10.1080/00319104.2018.1423564

G.L. Starova, O.V. Frank-Kamanetskaya, E.F. Shibanova, V.A. Lopyrev, М.G. Voronkov, V.V. Makarskii, X-ray diffraction examination of the molecular structure of guanazole (3,5-diamino-ih-i,2,4-triazole), Khimiya Geterotsiklicheskikh Soedinenii. 10, 1422-1423 (1979)

Y.Z Zheng, Y. Zhou, Q. Liang, D.F. Chen, R. Guo, R. C. Lai, Hydrogen-bonding Interactions between Apigenin and Ethanol/Water: A Theoretical Study SCI. REP-UK, 6, 34647-34660 (2016)

Doi:10.1038/srep34647

M. T. Bilkan, Structural and spectroscopic studies on dimerization and solvent-ligand complexes of Theobromine, J. Mol. Liq. 238, 523-532 (2017)

https://doi.org/10.1016/j.molliq.2017.05.051




DOI: http://dx.doi.org/10.20450/mjcce.2020.1926

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