Investigation of acidic properties of 2-ethoxy-6-(3-substitue-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl-azomethine)-phenyl benzoates

Yıl 2021, Cilt: 3 Sayı: 2, 39 - 44, 30.12.2021

Haydar Yüksek , Faruk Kardaş , Sevda Manap , Gül Özdemir

https://doi.org/10.51435/turkjac.940613

Cited By: 2

Öz

In this study, to determine the pKa values of 2-ethoxy-6-(3-substitue-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl-azomethine)-phenyl benzoates (1-9) were titrated potentiometrically with tetrabutylammonium hydroxide in four non-aqueous solvents such as isopropyl alcohol, tert-butyl alcohol, acetone and N,N-dimethylformamide (DMF), and graphs were drawn for all cases. In addition, the effects of solvents and molecular structure upon acidity compounds 1-9 were also determined and discussed. The half-neutralization potential values and the corresponding pKa values were determined by half neutralization method.

Anahtar Kelimeler

1, 2, 4-triazole, Schiff base, acidic properties, HNP, potentiometric titrations, pKa

Proje Numarası

2011-FEF-31

Kaynakça

• [1] A. Uzgören-Baran, B.C. Tel, D. Sargöl, E.I. Öztürk, I. Kazkayas, G. Okay, M. Ertan, B. Tozkoporan, Thiazolo[3,2-b]-1,2,4-triazole-5(6H)-one substituted with ibuprofen: Novel non-steroidal anti-inflammatory agents with favorable gastrointestinal tolerance. European Journal of Medicinal Chemistry, 57, 2012, 398–406.
• [2] N. Chidananda, B. Poojary, V. Sumangala, N.S. Kumari, P. Shetty, T. Arulmoli, Facile synthesis, characterization and pharmacological activities of 3,6-disubstituted 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 5,6-dihydro-3,6-disubstituted-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles, European Journal of Medicinal Chemistry, 51, 2012, 124–136.
• [3] M.A. Henen, S.A.A. El Bialy, F.E. Goda, M.N.A. Nasr, H.M. Eisa, [1,2,4]Triazolo[4,3-a]quinoxaline: Synthesis, antiviral, and antimicrobial activities. Medicinal Chemistry Research, 21, 2012, 2368–2378.
• [4] N. Demirbaş, R. Uğurluoğlu, Synthesis and antitumor activities of some new 4-(1-naphthylidenamino)- and 4-(1-naphthylmethylamino)-1,2,4-triazol-5-one derivatives, Turk J Chem, 28, 2004, 679-690.
• [5] Z. Li, Y. Cao, P. Zhan, C. Pannecouque, J. Balzarini, E De. Clercq, Synthesis and anti-HIV evaluation of novel 1,2,4-triazole derivatives as potential non-nucleoside HIV-1 reverse transcriptase inhibitors, Letters in Drug Design Discovery, 10, 2013, 27–34.
• [6] K.A. Ali, E.A. Ragab, T.A. Farghaly, M.M. Abdalla, Synthesis of new functionalized 3-substituted [1,2,4]triazolo [4,3-a]pyrimidine derivatives: potential antihypertensive agents. Acta Poloniae Pharmaceutica, 68, 2011, 237–47.
• [7] 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.
• [8] 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.
• [9] O. Aktas-Yokus, H. Yuksek, O. Gursoy-Kol, S. Alpay-Karaoglu, Synthesis and biological evaluation of new 1,2,4-triazole derivatives with their potentiometric titrations, Medicinal Chemistry Research, 24, 2015, 2813–2824.
• [10] O. Aktaş-Yokuş, H. Yüksek, S. Manap, F. Aytemiz, M. Alkan, M. Beytur, O. Gürsoy-Kol, In-vitro biological activity of some new 1,2,4-triazole derivatives with their potentiometric titrations, Bulgarian Chemical Communications, 49, 2017, 98-106.
• [11] E. Çiftçi, M., Beytur, M. Calapoğlu, M., Ö. Gürsoy Kol, M. Alkan, V.A. Toğay, S. Manap, H. Yüksek, Synthesis, characterization, antioxidant and antimicrobial activities and DNA damage of some novel 2-[3-alkyl (aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-phenoxyacetic acids in Human Lymphocytes, Res J Pharm Biol Chem Sci, 9, 2018, 1760-1771.
• [12] H. Yüksek, G. Özdemir, Ö. Gürsoy Kol, S., Manap, S. Buluttekin, S. Gökçe, M. Alkan, Synthesis, in vitro antioxidant and antimicrobial activities of some new 2-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl-azomethine)-phenyl benzenesulfonate derivatives, Journal of the Chemical Society of Pakistan, 42, 2020, 624-633.
• [13] 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.
• [14] L.G. Hargis, Analytical Chemistry Principles and Techniques, Prentice-Hall Inc., New Jersey, 1988.
• [15] T. Gündüz, E. Kılıç, V. Ertüzün and G. Çetinel, Titrations in non-aqueous media. Part V. Acid-base behaviour of substituted 2-amino-3-cyanofurans, 2-amino-3-cyanothiophenes and 2-amino-3-cyanopyrrole and their Schiff bases with salicylaldehyde and 2-hydroxy-1-naphthaldehyde, Analyst, 111, 1986, 1439-1442.
• [16] T. Gündüz, N. Gündüz, E. Kılıç, P. Gürkan, Titrations in non-aqueous media. Part VI. Effects of substituents on basicity or acidity of N-salicylidene-2-hydroxyaniline, Analyst, 112, 1987, 1057-1061.
• [17] A. Arslantaş, H. Yüksek, Ö. Gürsoy-Kol, Z. Ocak, Z. Tomruk, M. Calapoğlu, In-vitro antioxidant evaluation and DNA intercation of some novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, Asian J Chem, 24, 2012, 3327-3334.
• [18] G. Kortüm, W. Vogel, K. Andrussow, Dissociation Constants of Organic Acids in Aqueous Solution, Plenum Press, New York, 1961, P. 79.
• [19] V.A. Palm, Tables of Rate and Equilibrium Constants of Heterolytic Organic Reactions, Viniti, Moscow, 1976, P. 20.
• [20] K. Izutsu, Acid-base Dissociation Constants in Dipolar Aprotic Solvents, IUPAC Chemical Data Series, Blackwells Scientific, Oxford, 1990, P. 38.
• [21] F.G. Bordwell, Acc. Chem. Res, Equilibrium acidities in dimethyl sulfoxide solution, 21, 1988, 456–463.
• [22] F. İslamoğlu, H. Yüksek, M. Özdemir, Acidic properties of some 1,2,4-triazole derivatives in non-aqueous media, Der Chemica Sinica, 2(3), 2011, 117-124.
• [23] H. Yüksek, Z. Ocak, M. Özdemir, M. Ocak, M. Bekar, M. Aksoy, A Study on novel 4-heteroarylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones, Indian J Heterocy Ch, 13, 2003, 49-52.
• [24] H. Yüksek, Ş. Bahçeci, Z. Ocak, M. Alkan, B. Ermiş, T. Mutlu, M. Ocak, Synthesis of some 4,5-dihydro-1H-1,2,4-triazol-5-ones, Indian J Heterocy Ch, 13, 2004, 369-372.
• [25] 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.
• [26] M. Alkan, H. Yüksek, Ö. Gürsoy-Kol, M. Calapoğlu, Synthesis, acidic and antioxidant properties of some novel 3,4-disubstituted-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, Molecules, 13, 2008,107-121.
• [27] H. Yüksek, Ö. Gürsoy-Kol, Preparation, characterization and potentiometric titrations of some new di-[3-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethinphenyl] isophtalate /terephtalate derivatives, Turk J Chem, 33, 2008, 773-784.
• [28] Ö. Gürsoy-Kol, H. Yüksek, F. İslamoğlu, In vitro antioxidant and acidic properties of novel 4-(5-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Synthesis and characterization, Revista de Chimie (Bucharest), 63, 2012, 1103-1111.
• [29] 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.
• [30] 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.
• [31] 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.
• [32] 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.
• [33] G. Pekcan, A.H. Aktaş, Spectrophotometric determination of pK(a) values for some benzoic acid compounds in acetonitrile-water mixtures, Asian J Chem, 18, 2006, 2168-2178.
• [34] F. Kardaş, Ö. Gürsoy-Kol, M. Beytur, M., Alkan, H. Yüksek, Synthesis and In vitro antimicrobial properties of some new 4-(2-benzoxy-3-ethoxy)-benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, International Research Journal of Pure & Applied Chemistry, 15(2), 2017, 1-9.
• [35] Ö. Gürsoy-Kol, H. Yüksek, F. İslamoğlu, Synthesis and in vitro antioxidant activities of novel 4-(3-methyl-2-thienylmethylene-amino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives with their acidic properties, J Chem Soc Pak, 35(4), 2013, 1179-1190.
• [36] H. Yüksek, M. Alkan, Z. Ocak, Ş. Bahçeci, M. Ocak, M. Özdemir, Synthesis and acidic properties of some new potential biologically active 4-acylamino-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, Indian J of Chem, 43B, 2004, 1527-1531.
• [37] H. Yüksek, M. Küçük, M. Alkan, Ş. Bahçeci, S. Kolaylı, Z. Ocak, U. Ocak, E. Şahinbaş, M. Ocak, Synthesis and antioxidant activities of some new 4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives with their acidic properties, Asian J Chem, 18, 2006, 539-550.
• [38] H. Yüksek, M. Alkan, I. Çakmak, Z. Ocak, Ş. Bahçeci, M. Calapoğlu, M. Elmastaş, A. Kolomuç, H. Aksu, Preparation, GIAO NMR calculations and acidic properties of some novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives with their antioxidant activities, Int J Mol Sci, 9, 2008, 12-32.
• [39] Ö. Gürsoy Kol, H. Yüksek, Synthesis and In-vitro antioxidant evaluation of some novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, E-Journal of Chem, 7(1), 2010, 123-136.
• [40] Ş. Bahçeci, H. Yüksek, Z. Ocak, C. Köksal, M. Özdemir, Synthesis and non-aqueous medium titrations of some new 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, Acta Chemica Slovenica, 49, 2002, 783-794.