Nedime DÜRÜST, Yaşar DÜRÜST, Emine Özge GÖZLÜKAYA

NH-acidities and Hammett correlation of 3-para substituted phenyl-1,2,4-oxadiazol-5(4H)-ones and 1,2 l43,5-oxathiadiazole 2-oxides in nonaqueous media

NH acidities of some 3-(p-substitutedphenyl)-1,2,4-oxadiazol-5(4H)-ones and 4-(p-substitutedphenyl)-1,2 l43,5-oxathiadiazole 2-oxides were determined in methanol by means of potentiometric titration with sodium methoxide. pKa values of the title compounds calculated from the potentiometric data were interpreted on the basis of structural effects caused by para-substituted groups on the phenyl ring by plotting pKa values versus Hammett sp+ constants, which gave excellent linear correlations.

Anahtar Kelimeler:

Potentiometry, oxadiazol-5(4H)-one, oxathiadiazol 2-oxide, linear Hammett correlation

NH-acidities and Hammett correlation of 3-para substituted phenyl-1,2,4-oxadiazol-5(4H)-ones and 1,2 λ 43,5-oxathiadiazole 2-oxides in nonaqueous media

Keywords:

Potentiometry, oxadiazol-5(4H)-one, oxathiadiazol 2-oxide, linear Hammett correlation,

PDF

___

Wermuth, C. G. In The Practice of Medicinal Chemistry ; 2nd ed.; Wermuth, C. G., Ed., Academic Press: London, UK, 2003.
Kohara, Y.; Kubo, K.; Imamiya, E.; Wada, T.; Inada, Y.; Naka, T. J. Med. Chem. 1996, 39, 5228–5235.
Boschelli, D. H.; Connor, D. T. U.S. Patent 5,114,958, May 19, 1992.
Dong, C. Z.; Ahamada-Himidi, A.; Plocki, S.; Aoun, D.; Touaibia, M.; Meddad-Bel Habich, N.; Huet, J.; Redeuilh, C.; Ombetta, J. E.; Godfrold, J. J.; et al. Bioorg. Med. Chem. 2005, 13, 1989–2007.
Valgeirsson, J.; Nielsen, E.; Peters, D.; Mathiesen, C.; Kristensen, A. S.; Madsen, U. J. Med. Chem. 2004, 47, 6948–6957.
Schroeder, A.; Kotthaus, J.; Schade, D.; Clement, B.; Rehse, K. Archiv Pharm. 2010, 343, 9–16.
Clement, B.; Reeh, C.; Hungeling, H. Ger. Offen. 2009, DE 102008007381 A1 20090813.
Bolton, R. E.; Coote, S. J.; Finch, H.; Lowdon, A.; Pegg, N.; Vinader, M. V. Tetrahedron Lett. 1995, 36, 4471–4474. Nardi, A.; Demnitz, J.; Grunnet, M.; Christophersen, P.; Jones, D. S.; Nielsen, E. O.; Stroebaek, D.; Madsen, L. S. PCT Int. Appl. 2008 WO 2008135591 A1 20081113.
Kohara,Y.; Imamiya, E.; Kubo, K.; Wada, T.; Inada, Y.; Naka, T. Bioorg. Med. Chem. Lett. 1995, 5, 1903–1908. Ellingboe, J. W.; Alessi, T. R.; Dolak, T. M.; Nguyen, T. T.; Tomer, J. D.; Guzzo, F. S.; Bagli, J. F.; McCaleb, M. L. J. Med. Chem. 1992, 35, 1176–1183.
Fritz, J. S. Acid-Base Titrations in Non-Aqueous Solvents; Allyn and Bacon: Boston, USA, 1973.
Dewick, P. M. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry ; John Wiley & Sons: Chichester, West Sussex, UK, 2006.
Rochester, C. H. Acidity Functions, in Organic Chemistry, Ed. Blomquist, A. T. Academic Press, London, UK, 19 G¨ und¨ uz, T.; Kılı¸ c, E.; Atakol, O.; K¨ oseo˘ glu, F. Analyst 1989, 114, 475–477.
Akay, A.; D¨ ur¨ ust, N.; D¨ ur¨ ust, Y.; Kılı¸ c, E. Anal. Chim. Acta 1999, 392, 343–346.
D¨ ur¨ ust, N.; Akay, A.; D¨ ur¨ ust, Y.; Kılı¸ c, E. Anal. Sci. 2000, 16, 825–827.
D¨ ur¨ ust, Y.; D¨ ur¨ ust, N.; Akcan, M. J. Chem. Eng. Data 2007, 52, 718–720.
D¨ ur¨ ust, Y. Phosphorus Sulfur Silicon 2009, 184, 2923–2935.
D¨ ur¨ ust, Y.; Akcan, M.; Martiskainen, O.; Siirola, E.; Pihlaja, K. Polyhedron 2008, 27, 999–1007.
D¨ ur¨ ust, Y.; Yıldırım, M.; Aycan, A. J. Chem. Res. 2008, 4, 235–239.
Nicolaides, D. N.; Varella, E. A. In: The Chemistry of Acid Derivatives Vol. 2. Suppl. B., Patai, S. Ed., Wiley: New York, NY, USA, 1992.
Eloy, F.; Lenaers, R. Chem. Rev. 1962, 62, 155–183.
Deegan, T. L.; Nitz, T. J.; Cebzanov, D.; Pufko, D. E.; Porco, J. A. Jr. Bioorg. Med. Chem. Lett. 1999, 9, 209–212. Kitamura, S.; Fukushi, H.; Miyawaki, T.; Kawamura, M.; Konishi, N.; Terashita, Z. I.; Naka, T. J. Med. Chem. 2001, 44, 2438–2450.
Dias, A. M.; Cabral, I. M.; Vila-Ch˜ a, A. S.; Cunha, D. P.; Senhor˜ aes, N.; Nobre, S. M.; Sousa, C. E.; Proen¸ ca, M. F. Synlett 2010, 2792–2796.
Kohara, Y.; Kubo, K.; Imamiya, E.; Wada, T.; Inada, Y.; Naka, T. J. Med. Chem. 1996, 39, 5228–5235.
Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 2, 165–195.
Fern´ andez, I.; Frenking, G. J. Org. Chem. 2006, 71, 2251–2256.
Yoshida, T.; Hirozumi, K.; Harada, M.; Hitaoka, S.; Chuman, H. J. Org. Chem. 2011, 76, 4564–4570.
Sarmini, K.; Kenndler, E. J. Biochem. Biophys. Methods 1999, 38, 123–137.
K¨ utt, A.; Leito, I.; Kaljurand, I.; Soovali, L.; Vlasov, V. M.; Yagupolskii, L. M.; Koppel, I. A. J. Org. Chem. 2006, 71, 2829–2838.
Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456–463.
Bordwell, F. G; Liu, W. Z. J. Phys. Org. Chem. 1998, 11, 397-406.
Zhao, Y. Y.; Bordwell, F. G.; Cheng, J. P.; Wang, D. F. J. Am. Chem. Soc. 1997, 119, 9125–9129.