Synthesis and determination of pKa values of some new di-{2-ethoxy-6-[(3-substitue-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)azomethine]phenyl} terephthalates

Year 2022, Volume: 4 Issue: 1, 31 - 36, 29.06.2022

Faruk Kardaş , Haydar Yüksek , Zafer Ocak

https://doi.org/10.51435/turkjac.1109562

Abstract

In this study, seven novel di-{2-ethoxy-6-[(3-substitue-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)azomethine]phenyl} terephtalates (4a-g) were synthesized from the rections of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (2a-g) with di-(2-formyl-6-ethoxyphenyl) terephtalate (3). The compounds 4a-g were characterized using by IR, 1H-NMR, 13C-NMR and UV spectral data. In addition, 4 type compounds were titrated potentiometrically with tetrabutylammonium hydroxide in four non-aqueous solvents such as isopropanol, tert-butanol, dimethyl ketone, N,N-dimethylformamide and the half-neutralization potential values and the corresponding pKa values were determined for all cases.

Keywords

1,2,4-triazole, Schiff base, acidity, potentiometric titrations, pKa

Supporting Institution

Scientific Research Projects Coordination Unit of Kafkas University

Project Number

2011-FEF-31

References

• [1] H. Yüksek, O. Üçüncü, M. Alkan, Z. Ocak, Ş. Bahçeci, Non-aqueous medium titrations of some new 4-benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, Molecules, 10, 2005, 961-970.
• [2] H. Yüksek, Ö. Aktaş-Yokuş, Ö. Gürsoy-Kol, Ş. Alpay-Karaoğlu, In vitro biological activity of some new 1,2,4-triazole derivatives with their potentiometric titrations, Indian J of Chem Sect B, 56B, 2017, 567-577.
• [3] Ö. Gürsoy-Kol, H. Yüksek, F. İslamoğlu, Synthesis and in vitro antioxidant activities of novel 4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives with their acidic properties, J Chem Soc Pak, 35(4), 2013, 1179-1190.
• [4] Ö. Aktaş-Yokuş, H. Yüksek, Ö. Gürsoy-Kol, Ş. Alpay-Karaoğlu, Synthesis and biological evaluation of new 1,2,4-triazol derivatives with their potentiometric titrations, Med Chem Res, 24, 2015, 2813–2824.
• [5] H. Yüksek, F. Kardaş, S. Manap, G. Özdemir, Investigation of acidic properties of 2-ethoxy-6-(3-substitue-4,5-dihydro-1H1,2,4-triazol-5-one-4-yl-azomethine)-phenyl benzoates, Turk J Anal Chem, 3(2), 2021, 39-44.
• [6] H. Yüksek, O. Kutanis, S. Manap, G. Özdemir, Z. Ocak, Non-Aqueous medium titrations of some 3-alkyl(aryl)-4-[3-(2-metylbenzoxy)-4-methoxybenzylideneamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones, Turk J Anal Chem, 3(2), 2021, 54-58.
• [7] P.A. Frey, F.C. Kokesh, F.H. Westheimer, A reporter group at active site of acetoacetate decarboxylase. I. Ionization constant of the nitrophenol, Journal of the American Chemical Society, 93, 1971, 7266–7269.
• [8] A. Demirbaş, I. Kula, Y. Erdoğan, A. Aslan, N. Yaylı, S. Karslıoğlu, Non-aqeous medium titration of some acidic compounds, Energy Education Science and Technology, 1, 1998, 13–16.
• [9] A.E. Putun, G. Bereket, E. Keskin, Potentiometric titrations of some 2-substituted 5-nitrobenzimidazole derivatives in nonaqueous solvent, Journal of Chemical & Engineering Data, 40, 1995, 221–224.
• [10] H. Yüksek, O. Akyıldırım, M.L. Yola, Ö. Gürsoy-Kol, M. Çelebier, D. Kart, Synthesis, in vitro antimicrobial and antioxidant activities of some new 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, Archiv Der Pharmazie, 346 (6), 2013, 470-480.
• [11] H. Yüksek, A. Demirbaş, A. İkizler, C.B. Johansson, C. Çelik, A.A. İkizler, Synthesis and antibacterial activities of some 4,5-dihydro-1H-1,2,4-triazol-5-ones, Arzneim-Forsch/Drug Res, 47, 1997, 405-409.
• [12] S. Boy, F. Türkan, M. Beytur, A. Aras, O. Akyıldırım, H. Sedef Karaman, H. Yüksek, Synthesis, design, and assessment of novel morpholine-derived Mannich bases as multifunctional agents for the potential enzyme inhibitory properties including docking study, Bioorganic Chemistry, 107, 2021, 104524.
• [13] Ö. Gürsoy-Kol, S. Manap, G. Özdemir, M. Beytur, E. Agdaş, F. Azap, S. Yuca, M. Alkan, H. Yüksek, Synthesis, antioxidant and antimicrobial activities of novel 4-(2-cinnamoyloxy-benzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, Heterocyclic Letters, 10(4), 2020, 575-587.
• [14] A. Ikizler, R. Un, Reactions of ester ethoxycarbonylhydrazones with some amine type compounds, Chimica Acta Turcia, 7, 1979, 269–290.
• [15] A. Ikizler, H. Yüksek, Acetylation of 4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones, Organic Preparations and Procedures International, 25(1), 1993, 99–105.
• [16] Ş. Bahçeci, Z. Ocak, N. Yıldırım, H. Yüksek, Solvent and molecular structure effects on acidity strength in non-aqueous medium, Turk J Anal Chem, 3(1), 2021, 27-32.
• [17] T. Gündüz, İnstrümental Analiz, (6. Edition), 2001, Ankara, Ankara Üniversitesi Fen Fakültesi Yayınları.
• [18] Ö. A. Yokuş, H. Yüksek, Ö. G. Kol, Ş. A. Karaoğlu, Synthesis and biological evaluation of new 1,2,4-triazole derivatives with their potentiometric titrations, Medicinal Chemistry Research, 24, 2015, 2813–2824.
• [19] M. Alkan, A. Gürbüz, H. Yüksek, Ö G. Kol, Z. Ocak , Synthesis and non-aqueus medium titrations of some new 3-alkyl(aryl)-4-[2-(4-methoxybenzoxy)- 3-methoxy]-benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones, Caucasian J. of Science, 1(1), 2014, 138-147.
• [20] T. Gündüz, Susuz Ortam Reaksiyonları, 1998, Ankara, Gazi Büro Kitabevi Tic. Ltd. Şti.,