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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
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.

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.,
Year 2022, Volume: 4 Issue: 1, 31 - 36, 29.06.2022
https://doi.org/10.51435/turkjac.1109562

Abstract

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.,
There are 20 citations in total.

Details

Primary Language English
Subjects Analytical Chemistry
Journal Section Research Articles
Authors

Faruk Kardaş 0000-0002-0900-7503

Haydar Yüksek 0000-0003-1289-1800

Zafer Ocak 0000-0002-6604-9814

Project Number 2011-FEF-31
Publication Date June 29, 2022
Submission Date April 26, 2022
Acceptance Date June 6, 2022
Published in Issue Year 2022 Volume: 4 Issue: 1

Cite

APA Kardaş, F., Yüksek, H., & Ocak, Z. (2022). 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. Turkish Journal of Analytical Chemistry, 4(1), 31-36. https://doi.org/10.51435/turkjac.1109562
AMA Kardaş F, Yüksek H, Ocak Z. 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. TurkJAC. June 2022;4(1):31-36. doi:10.51435/turkjac.1109562
Chicago Kardaş, Faruk, Haydar Yüksek, and Zafer Ocak. “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”. Turkish Journal of Analytical Chemistry 4, no. 1 (June 2022): 31-36. https://doi.org/10.51435/turkjac.1109562.
EndNote Kardaş F, Yüksek H, Ocak Z (June 1, 2022) 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. Turkish Journal of Analytical Chemistry 4 1 31–36.
IEEE F. Kardaş, H. Yüksek, and Z. Ocak, “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”, TurkJAC, vol. 4, no. 1, pp. 31–36, 2022, doi: 10.51435/turkjac.1109562.
ISNAD Kardaş, Faruk et al. “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”. Turkish Journal of Analytical Chemistry 4/1 (June 2022), 31-36. https://doi.org/10.51435/turkjac.1109562.
JAMA Kardaş F, Yüksek H, Ocak Z. 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. TurkJAC. 2022;4:31–36.
MLA Kardaş, Faruk et al. “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”. Turkish Journal of Analytical Chemistry, vol. 4, no. 1, 2022, pp. 31-36, doi:10.51435/turkjac.1109562.
Vancouver Kardaş F, Yüksek H, Ocak Z. 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. TurkJAC. 2022;4(1):31-6.