Abstract
The molecular parameters of 2,3,5-triphenyl-2H-tetrazolium chloride (TTC) and some compounds based on triphenylformazans (TPFs) — resulting from the enzymatic transformation of TTC, were subjected to comparative investigation on the basis of semi-empirical quantum-chemical simulations, revealing some changes in dipole moment and polarisability in the TPFs in comparison with TTC. Chemical shift due to substituents was discussed using electronic absorption bands in the UV-VIS range recorded for diluted solutions in various solvents as well as the absorption spectra recorded in the infrared range for KBr dispersions. The correlation of the spectral shift of the electronic absorption bands with a specific function on the solvent refractive index, as recommended by theoretical studies focused on solute-solvent interactions, revealed the major role played by dispersive and induction forces. For several solvents, a different behaviour could be assigned to specific interactions overlapping with universal solute-solvent interactions.
Similar content being viewed by others
References
Abe, T. (1965). Theory of solvent effects on molecular electronic spectra. Frequency shifts. Bulletin of the Chemical Society of Japan, 38, 1314–1318. DOI: 10.1246/bcsj.38.1314.
Awasthi, L. P., & Singh, S. P. (1982). Formazans and tetrazolium salts as potential antibacterial, antifungal, and antiviral agents. Zentralblatt für Mikrobiologie, 137, 503–507. DOI: 10.1016/s0232-4393(82)80008-5.
Bačkor, M., & Fahselt, D. (2005). Tetrazolium reduction as an indicator of environmental stress in lichens and isolated bionts. Environmental and Experimental Botany, 53, 125–133. DOI: 10.1016/j.envexpbot.2004.03.007.
Bakhshiev, N. G. (1972). Spektroskopiya mezhmolekulyarnykh vzaimodeistvii. Leningrad, Russia: Izd. Nauka. (in Russian)
Bharadwaj, S. D. (2002). Synthesis and biological activities of some new formazans, Part I. Asian Journal of Chemistry, 14, 767–770.
Bhupathiraju, V. K., Hernandez, M., Landfear, D., & Alvarez-Cohen, L. (1999). Application of a tetrazolium dye as an indicator of viability in anaerobic bacteria. Journal of Microbiological Methods, 37, 231–243. DOI: 10.1016/s0167-7012(99)00069-x.
Burdock, T., Brooks, M., Ghaly, A., & Deepika, D. (2011). Effect of assay conditions on the measurement of dehydrogenase activity of Streptomyces venezuelae using triphenyl tetrazolium chloride. Advances in Bioscience and Biotechnology, 2, 214–225. DOI: 10.4236/abb.2011.24032.
Coates, J. P. (2000). Interpretation of infrared spectra, a practical approach. In R. A. Meyers (Ed.), Encyclopedia of analytical chemistry (pp. 10815–10837). Chichester, UK: Wiley.
Erkoç, Ş., Tezcan, H., Çalişir, E. D., & Erkoç, F. (2006). Synthesis of bis-formazan molecule and quantum-chemical calculation. International Journal of Pure and Applied Chemistry, 1, 37–44.
Frederiks, W. M., van Marle, J., van Oven, C., Comin-Anduix, B., & Cascante, M. (2006). Improved localization of glucose-6-phosphate dehydrogenase activity in cells with 5-cyano-2,3-ditolyl-tetrazolium chloride as fluorescent redox dye reveals its cell cycle-dependent regulation. Journal of Histochemistry & Cytochemistry, 54, 47–52. DOI: 10.1369/jhc.5a6663.2005.
Gil-Agustí, M., Esteve-Romero, J., & Abraham, M. H. (2006). Solute-solvent interactions in micellar liquid chromatography: Characterization of hybrid micellar systems of sodium dodecyl sulfate-pentanol. Journal of Chromatography A, 1117, 47–55. DOI: 10.1016/j.chroma.2006.03.046.
Gökçe, G., Durmuş, Z., Tezcan, H., Kiliç, E., & Yilmaz, H. (2005). Electrochemical investigation of 1,3,5-triphenylformazan and its nitro derivatives in dimethyl sulfoxide. Analytical Sciences, 21, 685–688. DOI: 10.2116/analsci.21.685.
Hypercube (2011). HyperChem version 8.0.10 Package [computer software], Gainesville, FL, USA: Hypercube.
Jones, P. H., & Prasad, D. (1969). The use of tetrazolium salts as a measure of sludge activity. Journal (Water Pollution Control Federation), 41, R441–R449.
Kaliszan, R. (1993). Quantitative structure-retention relationships applied to reversed-phase high-performance liquid chromatography. Journal of Chromatography A, 656, 417–435. DOI: 10.1016/0021-9673(93)80812-m.
King, R. A., & Murrin, B. (2004). A computational study of the structure and synthesis of formazans. Journal of Physical Chemistry A, 108, 4961–4965. DOI: 10.1021/jp0400622.
Mahmoud, N. S., & Ghaly, A. E. (2004). Influence of temperature and pH on the nonenzymatic reduction of triphenyltetrazolium chloride. Biotechnology Progress, 20, 346–353. DOI: 10.1021/bp030029h.
Mariappan, G., Korim, R., Joshi, N. M., Alam, F., Hazarika, R., Kumar, D., & Uriah, T. (2010). Synthesis and biological evaluation of formazan derivatives. Journal of Advanced Pharmaceutical Technology and Research, 1, 396–400. DOI: 10.4103/0110-5558.76438.
Mataga, N., & Kubota, T. (1970). Molecular interactions and electronic spectra. New York, NY, USA: Marcel Dekker.
McRae, E. G. (1957). Theory of solvent effects of molecular electronic spectra. Frecquency shifts. Journal of Physical Chemistry, 61, 562–572. DOI: 10.1021/j150551a012.
Onsager, L. (1936). Electric moments of molecules in liquids. Journal of the American Chemical Society, 58, 1486–1493. DOI: 10.1021/ja01299a050.
Pechmann, H. V., & Runge, P. (1894). Oxydation der Formazylverbindungen. Berichte der Deutschen Chemischen Gesellschaft, 27, 323–324. DOI: 10.1002/cber.18940270165. (in German)
Pervova, I. G., Barachevskii, V. A., Melkozerov, S. A., Lipunova, G. N., Sigeikin, G. I., & Lipunov, I. N. (2010). A spectralkinetic study of the photochemical properties of 1-aryl-3-alkyl-5-(benzothiazol-2-yl)formazans. High Energy Chemistry, 44, 22–24. DOI: 10.1134/s0018143910010042.
Piaru, S. P., Mahmud, R., & Perumal, S. (2012). Determination of antimicrobial activity of essential oil of Myristica fragrans Houtt. using tetrazolium microplate assay and its cytotoxic activity against Vero cell line. International Journal of Pharmacology, 8, 572–576. DOI: 10.3923/ijp.2012.572.576.
Praveen-Kumar, & Tarafdar, J. C. (2003). 2,3,5-Triphenyltetrazolium chloride (TTC) as electron acceptor of culturable soil bacteria, fungi and actinomycetes. Biology and Fertility of Soils, 38, 186–189. DOI: 10.1007/s00374-003-0600-y.
Reichardt, C. (2003). Solvents and solvent effects in organic chemistry (3rd ed.). Weinheim, Germany: Wiley-VCH.
Ruf, M., & Brunner, I. (2003). Vitality of tree fine roots: reevaluation of the tetrazolium test. Tree Physiology, 23, 257–263. DOI: 10.1093/treephys/23.4.257.
Şenöz, H. (2012). The chemistry of formazans and tetrazolium salts. Hacettepe Journal of Biology and Chemistry, 40, 293–301.
Sigeikin, G. I., Lipunova, G. N., & Pervova, I. G. (2006). Formazans and their metal complexes. Russian Chemical Reviews, 75, 885–900. DOI: 10.1070/rc2006v075n10abeh003612.
Snyder, L. R., Carr, P. W., & Rutan, S. C. (1993). Solvatochromically based solvent-selectivity triangle. Journal of Chromatography A, 656, 537–547. DOI: 10.1016/0021-9673(93)80818-s.
Suppan, P. (1990). Invited review solvatochromic shifts: The influence of the medium on the energy of electronic states. Journal of Photochemistry and Photobiology A: Chemistry, 50, 293–330. DOI: 10.1016/1010-6030(90)87021-3.
Tezcan, H., Can, Ş., & Tezcan, R. (2002). The synthesis and spectral properties determination of 3-substituted phenyl-1,5-diphenylformazans. Dyes and Pigments, 52, 121–127. DOI: 10.1016/s0143-7208(01)00074-2.
Tezcan, H., & Ozkan, N. (2003). Substituent effects on the spectral properties of some 3-substituted formazans. Dyes and Pigments, 56, 159–166. DOI: 10.1016/s0143-7208(02)00131-6.
Tezcan, H. (2008). Synthesis and spectral properties of some bis-substituted formazans. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 69, 971–979. DOI: 10.1016/j.saa.2007.05.061.
Tezcan, H., & Uzluk, E. (2008). The synthesis and spectral properties of 1,3-substituted phenyl-5-phenylformazans and their Ni(II) complexes. Dyes and Pigments, 76, 733–740. DOI: 10.1016/j.dyepig.2007.01.016.
Tezcan, H., Uzluk, E., & Aksu, M. L. (2008). Electrochemical and structural properties of 1,3-substituted (-Cl, — Br) phenyl-5-phenylformazans. Journal of Electroanalytical Chemistry, 619–620, 105–116. DOI: 10.1016/j.jelechem.2008.03.013.
Tezcan, H., & Aksu, M. L. (2010). Electrochemical properties of 1-(o-,m-,p-nitrophenyl)-3-(m-nitrophenyl)-5-phenylformazans and their nickel complexes. Turkish Journal of Chemistry, 34, 465–479. DOI: 10.3906/kim-0903-4.
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Creanga, D., Nadejde, C. Molecular modelling and spectral investigation of some triphenyltetrazolium chloride derivatives. Chem. Pap. 68, 260–271 (2014). https://doi.org/10.2478/s11696-013-0429-2
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2478/s11696-013-0429-2