SYNTHESIS AND NON-AQUEUS MEDIUM TITRATIONS OF SOME NEW 3- ALKYL(ARYL)-4-[2-(4-METHOXYBENZOXY)- 3-METHOXY]- BENZYLİDENAMINO-4,5-DIHYDRO-1H-1,2,4-TRIAZOL-5-ONES

Year 2014, Volume: 1 Issue: 1, 138 - 148, 31.12.2014

Muzaffer Alkan , Abdurrahman Gürbüz Haydar Yüksek Özlem Gürsoy Kol Zafer Ocak

Abstract

In this study, seven new 3-alkyl(aryl)-4-[2-(4-methoxybenzoxy)-3-methoxy]-benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones were synthesized from the reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones with 3-methoxy-2-(4-methoxybenzoxy)-benzaldehyde, which was obtained from the reaction of 2-hydroxy-3-methoxybenzaldehyde with p-methoxybenzoyl chloride by using triethylamine. The new compounds synthesized were characterized by using 1H-NMR, 13CNMR and UV spectral data. In addition, to investigate the effects of solvents and molecular structure upon acidity, the prepared 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones were titrated potentiometrically with tetrabutylammonium hydroxide in four non-aqueous solvents, including acetone, isopropyl alcohol, DMSO and N,N-dimethylformamide. The half-neutralization potential values and the corresponding pKa values were determined for all cases.

Keywords

3-alkyl(aryl)-4-, 2-(4-methoxybenzoxy)-3-methoxy, -benzylidenamino-4.5-dihydro-1H-1.2.4-triazol-5-ones, potentiometric titration

References

• 1.Yüksek, H., Küçük, M., Alkan, M., Bahçeci, Ş., Kolaylı, S., Ocak, Z., Ocak, U., Şahinbaş, E. and Ocak, M., Asian J. Chem. 2006, 18, 539-550.
• 2.Yüksek, H., Kolaylı, S., Küçük, M., Yüksek, M. O., Ocak, U., Şahinbaş, E., Sivrikaya, E. and Ocak, M., Indian J. Chem. 2006, 45B, 715-718.
• 3.Bahçeci, Ş., Yüksek, H., Ocak, Z., Azaklı, A., Alkan, M. and Ozdemir., M. Collect. Czech. Chem. Commun. 2002, 67, 1215-1222.
• 4.Bahçeci, Ş., Yüksek, H., Ocak, Z., Köksal, C. and Ozdemir, M., Acta Chim. Slov. 2002, 49, 783-794.
• 5.Yüksek, H., Üçüncü, O., Alkan, M., Ocak, Z., Bahçeci, Ş. and Özdemir, M., Molecules, 2005, 10, 961-970.
• 6.Yüksek, H., Ocak, Z., Özdemir, M., Ocak, M., Bekar, M. and Aksoy, M., Indian J. Heterocyl. Chem. 2003, 13, 49-52.
• 7.Yüksek, H., Bahçeci, Ş., Ocak, Z., Alkan, M., Ermiş, B., Mutlu, T., Ocak, M. and Özdemir, M., Indian J. Heterocy. Chem., 2004, 13, 369-372.
• 8.Yüksek, H., Bahçeci, Ş., Ocak, Z., Özdemir, M., Ocak, M., Ermiş, B. and Mutlu, T., Asian J. Chem. 2005, 17, 195-201.
• 9.Yüksek, H., Gürsoy, Ö., Çakmak, İ. and Alkan, M., Magn. Reson. Chem. 2005, 43, 585-587
• 10.Yüksek, H., Çakmak, İ., Sadi, S. and Alkan, M., Int. J. Mol. Sci. 2005, 6, 219-229.
• 11.Ikizler, A.A. and Yüksek, H., Org. Prep. Proceed. Int. 1993, 25, 99-105.
• 12.Ikizler, A. A., Şentürk, H. B. and Ikizler, A., Doğa-Tr. J. Chem. 1991, 15, 345-354; [Chem. Abstr. 1992, 116, 173458x].
• 13.Ikizler, A.A., Ikizler, A., Şentürk, H.B. and Serdar, M., Doğa-Tr. Kimya D. 1988, 12, 57-66; [Chem. Abstr. 1988, 109, 238277q].
• 14.Yüksek, H., Alkan, M., Ocak, Z., Bahçeci, Ş., Ocak, M. And Özdemir, M., Indian J. Chem. 2004, 43B, 1527-1531.
• 15.Yüksek, H., Ocak, Z., Alkan, M., Bahçeci, Ş. and Özdemir, M., Molecules 2004, 9, 232-240.
• 16.İkizler, A. A., Şentürk, H. B. and İkizler, A., Doğa-Tr J. Of Chem., 1991, 15, 345.
• 17.Erdoğan, ., Aslan, A., Demirbaş, A. And Yaylı, N., Modelling. Measurement & Control C, AMSE Press, 1994, 46-49.
• 18.Fritz, J. S., Acid-Base Titrations in Nonaqueous Solvents, Allyn and Bacon Inc., Boston, 1973.
• 19.Gündüz, T., Kalitatif Analiz Ders Kitabı, Ankara Üniversitesi, Fen Fakültesi Yayınları, Ankara, 1975.
• 20.Gündüz, T., Susuz Ortam Reaksiyonları, Gazi Büro Kitabevi Tic. Ltd. Şti, Ankara, 1998.