Determination of HNP and pKa Values of Some 3-Alkyl(Aryl)-4-phthalimido-4,5-dihydro-1H-1,2,4-triazol-5-one Compounds by Semi-Neutralization Method

Yıl 2022, Cilt: 9 Sayı: 2, 95 - 104, 31.12.2022

Haydar Yüksek Sevda Manap Gül Özdemir

https://doi.org/10.48138/cjo.1200631

Öz

In this study, the effects of solvents and molecular structure upon acidity, five 3-alkyl(aryl)-4-phthalimido-4,5-dihydro-1H-1,2,4-triazol-5-ones (3-7) were potentiometrically titrated with tetrabutylammonium hydroxide (TBAH) in four different anhydrous solvents (isopropyl alcohol, acetonitrile, tert-butyl alcohol and N,N-dimethylformamide) and HNP and corresponding pKa values were determined by half-neutralization method for all cases.

Anahtar Kelimeler

124-Triazole, HNP, pKa, titration

Teşekkür

The authors thank Dr. Zafer Ocak for their contribution.

Bazı 3-Alkil(Aril)-4-ftalimido-4,5-dihidro-1H-1,2,4-triazol-5-on Bileşiklerinin Yarı-Nötralizasyon Metodu İle HNP ve pKa Değerlerinin Tayini

Öz

Bu çalışmada, asitlik üzerine çözücü ve moleküler yapının etkilerini incelemek için, beş 3-alkil(aril)-4-ftalimido-4,5-dihidro-1H-1,2,4-triazol-5-on (3-7) bileşiğinin dört farklı susuz çözücüde (izopropil alkol, asetonitril, tert-butil alkol ve N,N-dimetilformamid) tetrabutilamonyum hidroksitle (TBAH) potansiyometrik olarak titrasyonları yapılmış ve yarı nötralizasyon yöntemi ile HNP ve karşın olan pKa değerleri her durum için tayin edilmiştir.

Anahtar Kelimeler

124-Triazol, HNP, pKa, titrasyon

Kaynakça

• Aktaş-Yokuş, Ö., Yüksek, H., Manap, S., Aytemiz, F., Alkan, M., Beytur, M., Gürsoy-Kol, Ö. (2017). In-vitro biological activity of some new 1,2,4-triazole derivatives with their potentiometric titrations. Bulgarian Chemical Communications, 49(I), 98-106.
• Aktaş-Yokuş, Ö., Yüksek, H., Gürsoy-Kol, Ö., Alpay-Karaoğlu, S. (2020). Synthesis and biological evaluation of new 1,2,4-triazole derivatives with their potentiometric titrations. Medicinal Chemistry Research, 24, 2813–2824.
• Alkan, M., Yüksek, H., İslamoğlu, F., Bahçeci, Ş., Calapoğlu, M., Elmastaş, M., Akşit, H., Özdemir, M. (2007). A study on 4-acylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones. Molecules, 12, 1805-1816.
• Bahçeci, Ş., Yüksek, H., Ocak, Z., Köksal, C., Özdemir, M. (2002). Synthesis and non-aqueous medium titrations of some new 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Acta Chemica Slovenica, 49, 783-794.
• Demirbaş, A., Kula, I., Erdoğan, Y., Aslan, A., Yaylı, N., Karslıoğlu, S. (1998). Non-aqeous medium titration of some acidic compounds. Energy Education Science and Technology, 1, 13–16.
• Demirbas, N., Ugurluoglu, R., Demirbas, A. (2002). Synthesis of 3-alkyl(aryl)-4-alkylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones and 3-alkyl-4-alkylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones as antitumor agents. Bioorganic & Medicinal Chemistry, 10, 3717–3723.
• Frey, P. A., Kokesh, F. C., Westheimer, F. H. (1971). A reporter group at active site of acetoacetate decarboxylase. I. Ionization constant of the nitrophenol. Journal of the American Chemical Society, 93, 7266–7269.
• Gündüz, T., Gündüz, T. (2002). İnstrümental Analiz. 6. Baskı, Genişletilmiş ve Gözden Geçirilmiş, Gazi Kitabevi, Ankara, 1357s.
• Gürbüz, A., Alkan, M., Manap, S., Özdemir, G., Yüksek, H. (2021). Synthesis and antimicrobial activities of novel 2-methoxy-6-[(3-alkyl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethin]-phenyl benzoates with their nonaqueous medium titrations. World Journal of Pharmacy and Pharmaceutical Sciences, 10(9), 65-80.
• Gursoy-Kol, O., Yuksek, H., Islamoglu, F. (2012). 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, 1103–1111.
• Gürsoy-Kol, Ö., Manap, S., Ozdemir, G., Beytur, M., Agdaş, E., Azap, F., Yuca, S., Alkan, M., Yüksek, H. (2020). Synthesis, antioxidant and antimicrobial activities of novel 4-(2-cinnamoyloxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Heterocyclic letters, 10(4), 575-587.
• Henen, M. A., El Bialy, S. A. A., Goda, F. E., Nasr, M. N. A., Eisa, H. M. (2012). [1,2,4]Triazolo[4,3-a]quinoxaline: synthesis, antiviral, and antimicrobial activities. Medicinal Chemistry Research, 21, 2368–2378.
• Huber, W. (1967). Titrations in nonaqueous solvents. Express Translation Service, Academic Press Inc., New York.
• Ikizler, A. A., Un, R. (1979). Reactions of ester ethoxycarbonylhydrazones with some amine type compounds. Chimica Acta Turcica, 7, 269-290.
• İkizler, A. A., Erdoğan, Y. (1991). Determination of pKa values of some benzylidenamino compounds in non-aqueous media. Doğa-Tr. Journal Chemistry, 15, 337-344.
• İkizler, A. A., Şentürk, H. B., İkizler, A. (1991). pKa Values of some 1,2,4-triazole derivatives in non-aqueous media. Doğa-Tr. Journal Chemistry, 15, 345-354.
• Ikizler, A. A., Yuksek, H. (1993). Acetylation of 4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones. Organic Preparations and Procedures International, 25, 99-105.
• İkizler, A. A., Yüksek, H. (1996). A study on 4,5-dihydro-1H-1,2,4-triazol-5-ones. Revue Roumaine de Chimie, 41, 585-590.
• İslamoğlu, F., Ö. Yüksek, H., Özdemir, M. (2011). Acidic properties of some 1,2,4-triazole derivatives in non-aqueous media. Der Chemica Sinica, 2(3), 117-124.
• Kahveci, B., Ozil, M., Mentese, E., Bekircan, O., Buruk, K. (2008). Microwave-assisted synthesis and antifungal activity of some new 1H-1,2,4-triazole derivatives. Russian Journal of Organic Chemistry. 44, 1816–1820.
• Ocak, Z. (2003). Bazı yeni triazol türevlerinin potansiyometrik özellikleri. Doktora Tezi, KTÜ Fen Bilimleri Enstitüsü, Trabzon.
• Putun, A. E., Bereket, G., Keskin, E. (1995). Potentiometric titrations of some 2-substituted 5-nitrobenzimidazole derivatives in nonaqueous solvent. Journal of Chemical & Engineering Data, 40, 221–224.
• Skoog, D. A. and Leary, J. J. (1992). Principles of Instrumental Analysis. Saunders College Publishing, Orlando.
• Uzgoren-Baran, A., Tel, B.C., Sarigol, D., Ozturk, E.I., Kazkayasi, I. Okay, G., Tozkoporan, M. B. (2012). 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: 398–406.
• Yüksek, H., Gürsoy-Kol, Ö. (2008). 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 Journal of Chemistry, 33, 773-784.
• Yüksek, H., Aktaş-Yokuş, Ö., Gürsoy-Kol, Ö., Alpay-Karaoğlu, Ş. (2017). In vitro biological activity of some new 1,2,4-triazole derivatives with their potentiometric titrations. Indian Joutnal of Chemistry Section B, 56B, 567-577.
• Yüksek, H., Özdemir, G., Gürsoy Kol, Ö., Manap, S., Buluttekin, S., Gökçe, S., Alkan, M. (2020). 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(04), 624-633.