Solvatochromism studies on UV spectra of 4,5-disubstituted-1,2,4-triazoline-3-thiones

Vesna B. Dimova, Nada U. Perišić-Janjić

Abstract


The influence of a series of organic solvents on the UV spectra of investigated 1,2,4-triazoles, was studied by implementing solvatochromic theory. As a part of our efforts to interpret the effects of solvent polarity and hydrogen bonding on the absorption spectra of previously synthesized 1,2,4-triazoline-3-thiones, the study design was based on the linear solvation energy relationship (LSER) concept using Kamlet-Taft solvatochromic parameters: π*, α and β. Accordingly, by dividing the solvents into two groups (protic and aprotic) it was ascertained that improved solvatochromic three-correlation models for the group of protic solvents were obtained. The results show that the solvent effect on UV absorption spectra of investigated thiones was very complex and strongly dependent on the nature of the substituent in positions 4 and 5 in 1,2,4-triazole moiety. Moreover, the statistical evaluation of the models (R, SD, Q2 and PRESS/SSY) showed satisfactory values.

Keywords


1,2,4-triazoline-3-thiones; UV spectra; solvent effects; LSER concept

Full Text:

PDF

References


M. Lazarević, V. Dimova, J. Csanadi, M. Popsavin, Lj. Klisarova, Synthesis of some new 4,5-disubstituted- 2,4-dihidro-3H-1,2,4-triazoline-3-thiones, Bull. Chem. Technol. Macedonia 16 (1997), 97– 103.

N. Perisic-Janjic, M. Acinski, N. Janjic, M. Lazarevic, V. Dimova, Study of the lipophilicity of some 1,2,4-triazole derivatives by RPHPLC and TLC, Journal of Planar Chromatography 13 (2000), 281–284.

M. Lazarevic, V. Dimova, D. Molnar Gabor, V. Kakurinov, K. Colanceska, Synthesis of some N1- aryl/heteroarylaminomethyl/ethyl-1,2,4-triazoles and their antibacterial and antifungal activities, Heterocyclic Communications 7 (2001), 577–582.

K. Colanceska, V. Dimova, V. Kakurinov, D. Molnar- Gabor, A. Buzarovska, Synthesis and antibacterial and antifungal activity of 4-substituted-5- aryl-1,2,4-triazole, Molecules 6 (2001), 815–824.

V. Dimova, K. Colanceska Ragenovic, V. Kakurinov, N1-aryl/heteroarylaminometil/ethyl-1,2,4-triazoles, Part II: Antimicrobial activity against Bacillus subtilis, Int. J. Mol. Sci. 7 (2006), 119–129.

V. Dimova, N. Perišić-Janjić, QSAR study by 1,2,4-triazoles using several physicochemical descriptors, Maced. J. Chem. Chem. Eng. 28 (2009), 79–89.

V. Daniloska, J. Blazevska-Gilev, V. Dimova, R. Fajgar, R. Tomovska, UV light induced surface modification of hdpe films with bioactive compounds, Applied Surface Science 256 (2010), 2276–2283.

V. Dimova, A study of behaviour of some 5-substituted- 4-phenyl-1,2,4-triazoline-3-thiones in sulfuric acid solution using characteristic vector analysis, Turk J Chem. 35 (2011), 109–120.

D. H. Purohit, B. L. Dodiya, R. M. Ghetiya, P. B. Vekariya, H. S. Joshi, Synthesis and Antimicrobial Activity of Some New 1,3,4-Thiadiazoles and 1,3,4-Thiadiazines Containing 1,2,4-Triazolo Nucleus, Acta Chim. Slov. 58 (2011), 53–59.

M. Pitucha, B. Polak, M. Swatko-Ossor, Ł. Popiołek, G. Ginalskac, Determination of the lipophilicity of some new derivatives of thiosemicarbazide and 1,2,4-triazoline-5-thione with potential antituberculosis activity, Croat. Chem. Acta 83 (2010), 299–306.

C. Öğretir, Y. Gülseven Sidir, İ. Sider, E. Taşal, Quantum chemical studies on tautomerism and basicity behavior of some 1,2,4-triazole derivatives, Turk J Chem. 34 (2010), 977–988.

U. Karakuş, B. Çoruh, E. Barlas-Durgun, M. Vázquez-López, S. Özbaş-Turan, J. Akbuğa1, S. Rollas, Synthesis and cytotoxic activity of some 1,2,4-triazoline-3-thione and 2,5-disubstituted- 1,3,4-thiadiazole derivatives, Marmara Pharm. J. 14 (2010), 84–90.

K. Parmar, B. Suthar, S. Prajapati, A. Suthar, Synthesis and biological activity of novel 1,3,5-trisubstituted 1,2,4-triazole derivatives, J. Heterocycl. Chem. 47 (2010), 156–161.

C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, Wiley-VCH, Weinheim, 2004.

C. Reichardt, Solvatochromic Dyes as Solvent Polarity Indicators, Chem Rev. 94 (1994), 2319– 2358.

J. M. Kamlet, J. L. Abboud, R. W. Taft, The solvatochromic comparison metod. The π* scale of solvent solarities, J Am Chem Soc. 99 (1977), 6027–6038.

J. M. Kamlet, J. L. Abboud, M. H. Abraham, R. W. Taft, Linear solvation energy relationships. A comprehensive collection of the solvatochromic parameters, π*, α, β and some methods for simplifying the generalized solvatochromic equation, J Org Chem. 48 (1983), 2877–2887.

Y. Marcus, The properties of organic liquids that are relevant to their use as solvating solvents, Chem Soc Rev. 22 (1993), 409–416.

A. Kawski. On the Estimation of Excited-State Dipole Moments from Solvatochromic Shifts of Absorption and Fluorescence Spectra, Z. Naturforsch, A: Phys Sci. 57A (2002), 255–262.

M. Jabbari, F. Gharib, Solvent Effects on Protonation Equilibria of Some Amino Acids and Peptides in Different Aqueous Solutions of Ethanol, Acta Chim. Slov. 57 (2010), 325–331.

A. Oehlke, K. Hofmann, S. Spange, New aspects on polarity of 1-alkyl-3-methylimidazolium salts as measured by solvatochromic probes, New J. Chem. 30 (2006), 533–536.

N. D. Divjak, N. R. Banjac, N. V. Valentić, G.S. Ušćumlić, Synthesis, structure and solvatochromism of 5-methyl-5-(3- or 4-substituted phenyl) hydantoins, J. Serb. Chem. Soc. 74 (2009), 1195–1205.

G. S. Ušćumlić, J. B. Nikolić, The study of linear solvation energy relationship for the reactivity of carboxylic acids with diazodiphenylmethane in protic and aprotic solvents, J. Serb. Chem. Soc. 74 (2009), 1335–1357.

M. R. Hadjmohammadi, M. J. Chaichi, M. Yousefpour, Solvatochromism Effect of Different Solvents on UV-Vis Spectra of Flouresceine and its Derivatives, Iran. J. Chem. Chem. Eng. 27 (2008), 9–14.




DOI: http://dx.doi.org/10.20450/mjcce.2012.60

Refbacks

  • There are currently no refbacks.




Copyright (c) 2016 Vesna B. Dimova, Nada U. Perišić-Janjić

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.