BibTex RIS Kaynak Göster

A theoretical study on proton-gain behaviors of some azaindole derivatives

Yıl 2011, Cilt: 1 Sayı: 2, 149 - 167, 21.03.2011

Sevgül Çalış Halil Berber Ülkü Uysal Cemil Öğretir

Öz

The acidities, relative stabilities (RS), nucleophlicities (η) and proton affinities (PA) of eleven azaindole molecules were determined in both gas and liquid phases using semi-empirical AM1, PM3 and PM5 methods. The calculated pKa values were compared with those of experimental pKa values to search a possible correlation. The protonation centres and protonation patterns were elucidated by taking into account of the best fitting results

Anahtar Kelimeler

Proton gain azaindole derivatives semi-empirical calculation

Kaynakça

  • Açikkalp, E., Yildiz, K., Yarligan, S. and Ö#retir, C. (2001). Semiempirical gas phase study on tau- tomerizm of 2-hydroxy amino and mercapto benzimidazoles. Journal of Molecular Structure: THEOCHEM 536(2-3), 155-160.
  • Adler, T.K. and Albert, A. (1963). The biological and physical properties of the azaindoles. Journal of Medicinal Chemistry 6, 480-483.
  • CAChe Ab InitioVersion 6.1.12.33. Fujitsu Limited Life Science & Material Science Division. 9-3. Nakase 1-Chome Mihama-ku. Chiba City Chiba 261-8588 Japan. For Academic Use Only, Cus- tomer Serial #: 1503000423.
  • Chi, S.M., Choi, J-K., Yum, E.K. and Chi, D.Y. (2000). Palladium-catalyzed functionalization of 5- and 7-azaindoles. Tetrahedron Letters 41, 919–922.
  • CS Chemoffice Pro for Microsoft Windows. Cambridge Scientific Computing. Inc. 875 Massachusetts Avenue. Suite 61. Cambridge MA 2139. USA.
  • Elguero, J., Marzin, C., Katritzky, A.R. and Linda, P. (1976). The Tautomerism of Heterocycles. Kat- rizky A R and Boulton A J (Eds), Academic Press, New York.
  • Fang, Y-Q., Yuen, J. and Lautens, M. (2007). A general modular method of azaindole and thieno- pyrrole synthesis via Pd-catalyzed tandem couplings of gem-dichloroolefins. Journal of Organ- ic Chemistry 72, 5152-5160.
  • Güray, T., Açıkkalp, E., Ö#retir, C. and Yarlıgan, S. (2007). Quantum chemical studies on protonation of some substituted thiazole derivatives. Journal of Molecular Graphics and Modelling 26(1), 154-165.
  • Güven, A. and Ö#retir, C. (1998). Investigation of the structure and properties of the potentially tau- tomeric 5,7-dimethyl-6H-pyrrolo[3,4-d]pyridazines in the gas and aqueous phases using the AM1 and PM3/COSMO solvation method. Journal of Molecular Structure: THEOCHEM 430, 85-95.
  • Harris, J.M. (1987). Nucleophilicity, Advances in Chemistry Series, 215, Washington, DC.
  • Huestis, M.P. and Fagnou, K. (2009). Site-selective azaindole arylation at the azine and azole rings via n-oxide activation. Organic Letters 11(6), 1357-1360.
  • Hür, D. and Güven, A. (2002). The acidities of some indoles. Journal of Molecular Structure: THEOCHEM 583, 1-18.
  • Jaramillo, P., Domingo, L.R., Chamorro, E. and Pérez, P. (2008). A further exploration of a nucleo- philicity index based on the gas-phase ionization potentials. Journal of Molecular Structure: THEOCHEM 865, 68–72.
  • Jiang, J.H., Liu, X.F., Zhen, C.H., Zhou, Y.J., Zhu, J., Lv, J.G. and Sheng, C.Q. (2011). Acrosin struc- ture-based design, synthesis and biological activities of 7-azaindole derivatives as new acrosin inhibitor. Chinese Chemical Letters 22(3), 272-275.
  • Kanıskan, N. and Ö#retir, C. (2002). Investigation of acid–base behaviour of some 2- pyridylbenzimidazoles using semi-empirical methods. Journal of Molecular Structure: THEOCHEM 584(1-3), 45-52.
  • Katrizky, A.R. (1984). Comprehensive Heterocyclic Chemistry, Vol. 4, Pergamon Press, p. 497.
  • Katrizky, A.R., Boulton, A.J. and Lagowski, J.M. (1964). Advances in Heterocyclic Chemistry Vol. 3, Academic Press, New York and London.
  • Ö#retir, C., Açíkkalp, E. and Güray, T. (2001). Investigation of the acidity constants and Hammett re- lations of some oxazolo[4,5-b]pyridin derivatives using semiempirical AM1 quantum chemical calculation method. Journal of Molecular Structure: THEOCHEM 538(1-3), 107-116.
  • Ö#retir, C. and Kaypak, N.F. (2002). Quantum chemical calculations on the annular tautomerism of some indazole derivatives. 1. A gas phase study. Journal of Molecular Structure: THEOCHEM 583(1-3), 137-144.
  • Ö#retir, C., Özö#üt, D., Yarligan, S. and Arslan, T. (2006). Quantum chemical studies on acidity– basicity behaviours of some substituted pyridine derivatives. Journal of Molecular Structure: THEOCHEM 759(1-3), 73-78.
  • Ö#retir, C., Tay, N.F. Öztürk, . (2007). A theoretical study on protonation of some halogen substitut- ed pyridine derivatives. Journal of Molecular Graphics and Modelling 26(4), 740-747.
  • Ö#retir, C. and Tokay, N. (2004). Quantum chemical studies on stereoisomerism, annular prototau- tomerism and protonation of bipyrazoles. Journal of Molecular Structure: THEOCHEM 679(1- 2), 1-8.
  • Ö#retir, C., Yarlıgan, S., Demirayak, %. and Arslan, T. (2003). A theoretical approach to acidity– basicity behaviour of some biologically active 6-phenyl-4,5-dihydro-3(2H)-pyridazinone de- rivatives. Journal of Molecular Structure: THEOCHEM 666-667, 609-615.
  • Ohshiro, Y. and Kikuta, H. (2000). Activities of 7-azaindole derivatives as agricultural fungicides. Science and Technology 12, 15-20.
  • Reinecke, M.G., Sebastian, J.F., Johnson, H.W. and Pyun, C. (1971). NMR spectral study of some or- ganometallic derivatives of indoles. Journal of Organic Chemistry 36(21), 3091–3095.
  • Reinecke, M.G., Sebastian, J.F., Johnson, H.W. and Pyun, C. (1972). Effect of solvent and cation on the reaction of organometallic derivatives of indole with methyl iodide. Journal of Organic Chemistry 37(20), 3066–3068.
  • Speranza, M. (1986). The Reactivity of Heteroaromatic Compounds in the Gas Phase. Advanced Het- erocylic Chemistry 40, 25-104.
  • Veber, D.F. and Lwowski, W. (1964). 1-Arylisoindoles. Journal of American Chemical Society 86(19), 4152–4158.
  • Yakhontov, L.N. (1968). The Chemistry of Azaindoles [Pyrrolo[2,3]pyridines]. Uspekhi Khimii 37, 1258-1287; Russian Chemical Reviews (Engl. Transl.) 37, 551-565.
  • Yarlıgan, S., Ö#retir, C., Csizmadia, I.G., Acıkkalp, E., Berber, H. and Arslan, T. (2005). An ab initio study on protonation of some substituted thiazole derivatives. Journal of Molecular Structure: THEOCHEM 715(1-3), 199-203.

BAZI AZAİNDOL TÜREVLERİNİN PROTON ALMA DAVRANIŞLARININ TEORİK OLARAK İNCELENMESİ

Yıl 2011, Cilt: 1 Sayı: 2, 149 - 167, 21.03.2011

Sevgül Çalış Halil Berber Ülkü Uysal Cemil Öğretir

Öz

Yedi adet azaindol molekülünün asitlikleri, bağıl kararlılıkları (RS), nukleofilliği (") ve proton ilgileri (PA) yarı-deneysel AM1, PM3 ve PM5 yöntemleriyle hem gaz hem de sıvı fazlarda belirlenmiştir. Hesaplanan pKa değerleri ile deneysel deneysel pKa değerleri arasındaki olası ilişki araştırılmıştır. Protonlanma merkezleri ve protonlanma mekanizmaları için en uygun sonuç dikkate alınarak aydınlatılmıştır.

Anahtar Kelimeler

Proton gain azaindole derivatives semi-empirical calculation

Kaynakça

  • Açikkalp, E., Yildiz, K., Yarligan, S. and Ö#retir, C. (2001). Semiempirical gas phase study on tau- tomerizm of 2-hydroxy amino and mercapto benzimidazoles. Journal of Molecular Structure: THEOCHEM 536(2-3), 155-160.
  • Adler, T.K. and Albert, A. (1963). The biological and physical properties of the azaindoles. Journal of Medicinal Chemistry 6, 480-483.
  • CAChe Ab InitioVersion 6.1.12.33. Fujitsu Limited Life Science & Material Science Division. 9-3. Nakase 1-Chome Mihama-ku. Chiba City Chiba 261-8588 Japan. For Academic Use Only, Cus- tomer Serial #: 1503000423.
  • Chi, S.M., Choi, J-K., Yum, E.K. and Chi, D.Y. (2000). Palladium-catalyzed functionalization of 5- and 7-azaindoles. Tetrahedron Letters 41, 919–922.
  • CS Chemoffice Pro for Microsoft Windows. Cambridge Scientific Computing. Inc. 875 Massachusetts Avenue. Suite 61. Cambridge MA 2139. USA.
  • Elguero, J., Marzin, C., Katritzky, A.R. and Linda, P. (1976). The Tautomerism of Heterocycles. Kat- rizky A R and Boulton A J (Eds), Academic Press, New York.
  • Fang, Y-Q., Yuen, J. and Lautens, M. (2007). A general modular method of azaindole and thieno- pyrrole synthesis via Pd-catalyzed tandem couplings of gem-dichloroolefins. Journal of Organ- ic Chemistry 72, 5152-5160.
  • Güray, T., Açıkkalp, E., Ö#retir, C. and Yarlıgan, S. (2007). Quantum chemical studies on protonation of some substituted thiazole derivatives. Journal of Molecular Graphics and Modelling 26(1), 154-165.
  • Güven, A. and Ö#retir, C. (1998). Investigation of the structure and properties of the potentially tau- tomeric 5,7-dimethyl-6H-pyrrolo[3,4-d]pyridazines in the gas and aqueous phases using the AM1 and PM3/COSMO solvation method. Journal of Molecular Structure: THEOCHEM 430, 85-95.
  • Harris, J.M. (1987). Nucleophilicity, Advances in Chemistry Series, 215, Washington, DC.
  • Huestis, M.P. and Fagnou, K. (2009). Site-selective azaindole arylation at the azine and azole rings via n-oxide activation. Organic Letters 11(6), 1357-1360.
  • Hür, D. and Güven, A. (2002). The acidities of some indoles. Journal of Molecular Structure: THEOCHEM 583, 1-18.
  • Jaramillo, P., Domingo, L.R., Chamorro, E. and Pérez, P. (2008). A further exploration of a nucleo- philicity index based on the gas-phase ionization potentials. Journal of Molecular Structure: THEOCHEM 865, 68–72.
  • Jiang, J.H., Liu, X.F., Zhen, C.H., Zhou, Y.J., Zhu, J., Lv, J.G. and Sheng, C.Q. (2011). Acrosin struc- ture-based design, synthesis and biological activities of 7-azaindole derivatives as new acrosin inhibitor. Chinese Chemical Letters 22(3), 272-275.
  • Kanıskan, N. and Ö#retir, C. (2002). Investigation of acid–base behaviour of some 2- pyridylbenzimidazoles using semi-empirical methods. Journal of Molecular Structure: THEOCHEM 584(1-3), 45-52.
  • Katrizky, A.R. (1984). Comprehensive Heterocyclic Chemistry, Vol. 4, Pergamon Press, p. 497.
  • Katrizky, A.R., Boulton, A.J. and Lagowski, J.M. (1964). Advances in Heterocyclic Chemistry Vol. 3, Academic Press, New York and London.
  • Ö#retir, C., Açíkkalp, E. and Güray, T. (2001). Investigation of the acidity constants and Hammett re- lations of some oxazolo[4,5-b]pyridin derivatives using semiempirical AM1 quantum chemical calculation method. Journal of Molecular Structure: THEOCHEM 538(1-3), 107-116.
  • Ö#retir, C. and Kaypak, N.F. (2002). Quantum chemical calculations on the annular tautomerism of some indazole derivatives. 1. A gas phase study. Journal of Molecular Structure: THEOCHEM 583(1-3), 137-144.
  • Ö#retir, C., Özö#üt, D., Yarligan, S. and Arslan, T. (2006). Quantum chemical studies on acidity– basicity behaviours of some substituted pyridine derivatives. Journal of Molecular Structure: THEOCHEM 759(1-3), 73-78.
  • Ö#retir, C., Tay, N.F. Öztürk, . (2007). A theoretical study on protonation of some halogen substitut- ed pyridine derivatives. Journal of Molecular Graphics and Modelling 26(4), 740-747.
  • Ö#retir, C. and Tokay, N. (2004). Quantum chemical studies on stereoisomerism, annular prototau- tomerism and protonation of bipyrazoles. Journal of Molecular Structure: THEOCHEM 679(1- 2), 1-8.
  • Ö#retir, C., Yarlıgan, S., Demirayak, %. and Arslan, T. (2003). A theoretical approach to acidity– basicity behaviour of some biologically active 6-phenyl-4,5-dihydro-3(2H)-pyridazinone de- rivatives. Journal of Molecular Structure: THEOCHEM 666-667, 609-615.
  • Ohshiro, Y. and Kikuta, H. (2000). Activities of 7-azaindole derivatives as agricultural fungicides. Science and Technology 12, 15-20.
  • Reinecke, M.G., Sebastian, J.F., Johnson, H.W. and Pyun, C. (1971). NMR spectral study of some or- ganometallic derivatives of indoles. Journal of Organic Chemistry 36(21), 3091–3095.
  • Reinecke, M.G., Sebastian, J.F., Johnson, H.W. and Pyun, C. (1972). Effect of solvent and cation on the reaction of organometallic derivatives of indole with methyl iodide. Journal of Organic Chemistry 37(20), 3066–3068.
  • Speranza, M. (1986). The Reactivity of Heteroaromatic Compounds in the Gas Phase. Advanced Het- erocylic Chemistry 40, 25-104.
  • Veber, D.F. and Lwowski, W. (1964). 1-Arylisoindoles. Journal of American Chemical Society 86(19), 4152–4158.
  • Yakhontov, L.N. (1968). The Chemistry of Azaindoles [Pyrrolo[2,3]pyridines]. Uspekhi Khimii 37, 1258-1287; Russian Chemical Reviews (Engl. Transl.) 37, 551-565.
  • Yarlıgan, S., Ö#retir, C., Csizmadia, I.G., Acıkkalp, E., Berber, H. and Arslan, T. (2005). An ab initio study on protonation of some substituted thiazole derivatives. Journal of Molecular Structure: THEOCHEM 715(1-3), 199-203.
Toplam 30 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Araştırma Makalesi
Yazarlar

Sevgül Çalış

Halil Berber

Ülkü Uysal

Cemil Öğretir Bu kişi benim

Yayımlanma Tarihi 21 Mart 2011
Yayımlandığı Sayı Yıl 2011 Cilt: 1 Sayı: 2

Kaynak Göster

APA Çalış, S., Berber, H., Uysal, Ü., Öğretir, C. (2011). A theoretical study on proton-gain behaviors of some azaindole derivatives. Anadolu University Journal of Science and Technology B - Theoretical Sciences, 1(2), 149-167.
AMA Çalış S, Berber H, Uysal Ü, Öğretir C. A theoretical study on proton-gain behaviors of some azaindole derivatives. AUBTD-B. Ağustos 2011;1(2):149-167.
Chicago Çalış, Sevgül, Halil Berber, Ülkü Uysal, ve Cemil Öğretir. “A Theoretical Study on Proton-Gain Behaviors of Some Azaindole Derivatives”. Anadolu University Journal of Science and Technology B - Theoretical Sciences 1, sy. 2 (Ağustos 2011): 149-67.
EndNote Çalış S, Berber H, Uysal Ü, Öğretir C (01 Ağustos 2011) A theoretical study on proton-gain behaviors of some azaindole derivatives. Anadolu University Journal of Science and Technology B - Theoretical Sciences 1 2 149–167.
IEEE S. Çalış, H. Berber, Ü. Uysal, ve C. Öğretir, “A theoretical study on proton-gain behaviors of some azaindole derivatives”, AUBTD-B, c. 1, sy. 2, ss. 149–167, 2011.
ISNAD Çalış, Sevgül vd. “A Theoretical Study on Proton-Gain Behaviors of Some Azaindole Derivatives”. Anadolu University Journal of Science and Technology B - Theoretical Sciences 1/2 (Ağustos 2011), 149-167.
JAMA Çalış S, Berber H, Uysal Ü, Öğretir C. A theoretical study on proton-gain behaviors of some azaindole derivatives. AUBTD-B. 2011;1:149–167.
MLA Çalış, Sevgül vd. “A Theoretical Study on Proton-Gain Behaviors of Some Azaindole Derivatives”. Anadolu University Journal of Science and Technology B - Theoretical Sciences, c. 1, sy. 2, 2011, ss. 149-67.
Vancouver Çalış S, Berber H, Uysal Ü, Öğretir C. A theoretical study on proton-gain behaviors of some azaindole derivatives. AUBTD-B. 2011;1(2):149-67.
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