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

ocak, zafer; Kutanis, Osman; MANAP, Sevda; Ozdemir, Gul; yüksek, Haydar

doi:10.51435/turkjac.940812

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

Haydar YÜKSEK, (Kafkas Üniversitesi, Fen-Edebiyat Fakültesi, Kimya Bölümü, Kars, Türkiye)

Osman KUTANİS, (Kafkas Üniversitesi, Fen-Edebiyat Fakültesi, Kimya Bölümü, Kars, Türkiye)

Sevda MANAP, (Kafkas Üniversitesi, Fen-Edebiyat Fakültesi, Kimya Bölümü, Kars, Türkiye)

Gül ÖZDEMİR, (Kafkas Üniversitesi, Fen-Edebiyat Fakültesi, Kimya Bölümü, Kars, Türkiye)

Zafer OCAK (Kafkas Üniversitesi, Eğitim Fakültesi, Matematik ve Fen Bilimleri Eğitimi Bölümü, Kars, Türkiye)

Turkish Journal of Analytical Chemistry (Online)

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Yıl: 2021 Cilt: 3 Sayı: 2 Sayfa Aralığı: 54 - 55 Metin Dili: İngilizce DOI: 10.51435/turkjac.940812 İndeks Tarihi: 12-08-2022

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

Öz:

A series of 3-alkyl(aryl)-4-[3-(2-metylbenzoxy)-4-methoxybenzylideneamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones (1-9) were titrated potentiometrically with tetrabutylammonium hydroxide in four non-aqueous solvents such as isopropyl alcohol, tert-butyl alcohol, acetonitrile and N,N-dimethylformamide (DMF), and graphs were drawn for all cases. The half-neutralization potential values and the corresponding pKa values were determined by half neutralization method. Thus, the effects of solvents and molecular structure upon acidity were discussed.

Anahtar Kelime: 1 2 4-triazol-5-one Schiff base acidity potentiometric titrations pKa

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

[1] Ş. Bahçeci, H. Yüksek, Z. Ocak, İ. Azaklı, M. Alkan, M. Özdemir, Synthesis and potentiometric titrations of some new 4-(benzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives in non-aqueous media, Collect Czech Chem Commun, 2002, 67, 1215-1222.
[2] 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.
[3] 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.
[4] 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.
[5] 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.
[6] 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.
[7] 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.
[8] H. Yüksek, O. Kutanis, G. Özdemir, M. Beytur, S. Kara, Ö. Gürsoy Kol, M. Alkan, Synthesis, In vitro antioxidant and antimicrobial activities of some novel 2-methoxy-4-[(3-substitue-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)azomethine]phenyl 2-methylbenzoate derivatives, Res J Pharm Biol Chem Sci, 9(4), 2018, 501-512.
[9] H. Yüksek, F. İslamoğlu, Ö. Gürsoy Kol, Ş. Bahçeci, M. Bekar, M. Aksoy, In-vitro antioxidant activities of new 4,5-dihydro-1H-1,2,4-triazole-5-ones having thiophene ring with their acidic properties, E-Journal of Chem, 8(4), 2011, 1734-1746.
[10] 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.
[11] 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.
[12] 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.
[13] E. Çiftçi, M. Beytur, M. Calapoğlu, 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(5), 2018,1760-1771.
[14] H. Yüksek, G. Özdemir, S. Manap, Y. Yılmaz, G. Kotan, Ö. Gürsoy-Kol, M. Alkan, Synthesis and investigations of antimicrobial, antioxidant activities of novel di-[2-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethinephenyl] isophtalates and Mannich base derivatives, ACTA Pharmaceutica Sciencia, 58(1), 2020, 49-68 (2020).
[15] 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.
[16] 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.
[17] M. Alkan, H. Yüksek, F. İslamoğlu, Ş. Bahçeci, M. Calapoğlu, M. Elmastaş, H. Akşit, M. Özdemir, A Study on 4-Acylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones, Molecules, 12, 2007, 1805-1816.
[18] 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.
[19] G. Özdemir, H. Yüksek, S. Manap, Ö. Gürsoy Kol, Potentiometric titrations of new 1,3,5-tri-{4-[(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethin]-phenoxycarbonyl} benzenes, The Pharmaceutical and Chemical Journal, 5(4), 2018, 23-28.
[20] H. Yüksek, S. Manap, M. Beytur, Ö. Gürsoy-Kol, Z. Ocak, Susuz ortamda bazı 3-alkil(aril) 4 suksinimido 4,5 dihidro 1H 1,2,4 triazol 5 on bileşiklerinin asidik özellikleri, Kafkas Üniv Fen Bil Enst Derg, 6, 2013, 53-65.
[21] Ö. Gürsoy-Kol, Z. Ocak, H. Yüksek, Bazı 3-Alkil(Aril)-4-(3-asetoksibenzilidenamino)-4,5-dihidro-1H-1,2,4-triazol-5-on bileşiklerinin susuz ortam titrasyonları, Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 20(3), 2016, 518-523.
[22] M. Alkan, A. Gürbüz, H. Yüksek, Ö. Gürsoy-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 Journal of Science, 1, 2014, 138-148.
[23] 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.
[24] 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.
[25] 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.
[26] 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.
[27] T. Gündüz, Susuz Ortam Reaksiyonları, Gazi Büro Kitabevi Tic. Ltd. Şti. Ankara, Turkey, 1998.

APA	yüksek H, Kutanis O, MANAP S, Ozdemir G, ocak z (2021). 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. , 54 - 55. 10.51435/turkjac.940812
Chicago	yüksek Haydar,Kutanis Osman,MANAP Sevda,Ozdemir Gul,ocak zafer 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. (2021): 54 - 55. 10.51435/turkjac.940812
MLA	yüksek Haydar,Kutanis Osman,MANAP Sevda,Ozdemir Gul,ocak zafer 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. , 2021, ss.54 - 55. 10.51435/turkjac.940812
AMA	yüksek H,Kutanis O,MANAP S,Ozdemir G,ocak z 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. . 2021; 54 - 55. 10.51435/turkjac.940812
Vancouver	yüksek H,Kutanis O,MANAP S,Ozdemir G,ocak z 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. . 2021; 54 - 55. 10.51435/turkjac.940812
IEEE	yüksek H,Kutanis O,MANAP S,Ozdemir G,ocak z "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." , ss.54 - 55, 2021. 10.51435/turkjac.940812
ISNAD	yüksek, Haydar vd. "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". (2021), 54-55. https://doi.org/10.51435/turkjac.940812

APA	yüksek H, Kutanis O, MANAP S, Ozdemir G, ocak z (2021). 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. Turkish Journal of Analytical Chemistry (Online), 3(2), 54 - 55. 10.51435/turkjac.940812
Chicago	yüksek Haydar,Kutanis Osman,MANAP Sevda,Ozdemir Gul,ocak zafer 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. Turkish Journal of Analytical Chemistry (Online) 3, no.2 (2021): 54 - 55. 10.51435/turkjac.940812
MLA	yüksek Haydar,Kutanis Osman,MANAP Sevda,Ozdemir Gul,ocak zafer 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. Turkish Journal of Analytical Chemistry (Online), vol.3, no.2, 2021, ss.54 - 55. 10.51435/turkjac.940812
AMA	yüksek H,Kutanis O,MANAP S,Ozdemir G,ocak z 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. Turkish Journal of Analytical Chemistry (Online). 2021; 3(2): 54 - 55. 10.51435/turkjac.940812
Vancouver	yüksek H,Kutanis O,MANAP S,Ozdemir G,ocak z 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. Turkish Journal of Analytical Chemistry (Online). 2021; 3(2): 54 - 55. 10.51435/turkjac.940812
IEEE	yüksek H,Kutanis O,MANAP S,Ozdemir G,ocak z "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." Turkish Journal of Analytical Chemistry (Online), 3, ss.54 - 55, 2021. 10.51435/turkjac.940812
ISNAD	yüksek, Haydar vd. "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". Turkish Journal of Analytical Chemistry (Online) 3/2 (2021), 54-55. https://doi.org/10.51435/turkjac.940812