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Theorıtıcal Calculatıon Of Pka Of 1,2,4-Trıazole And Its Derıvatıves

Yıl 2011, Cilt: 24 Sayı: 2, 51 - 70, 30.12.2011

Öz

In the present resarch the acidity values pKa of  eight 1,2,4-triazole derivatives were calculated by using physicochemical semi-empirical methods (AM1,PM3,PM5) .CAChe 6.0 experimental pKa  values were compared to theoretical results  calculated with semi-empirical methods. It was found that the calculation methods using thermokinetic parameters and most experimental results werein good agurement.

Kaynakça

  • [1] B. Modzelewska-Banachiewicz, J. Banachiewicz, A. Chodkowska, E. Jagiello-Wojtowicz, L. Mazur. Synthesis and Biological Activity of New Derivatives of 3-(3,4-Diaryl-1,2,4-triazole-5-yl) propenoic Acid, Eur. J. Med. Chem. Vol.39, pp. 873–877, 2004.
  • [2] W. Cheng-Xi, D.Xian-Qing, C.Kyu-Yun, S.Zhi-Gang and Q.Zhe-Shan. Synthesis and Anticonvulsant Activity of 1-Formamide-triazolo[4,3-a]quinoline Derivatives, Arch. Pharm. Res. Vol. 33, No 5, pp.655-662, 2010.
  • [3] X. Jianming, C.Yongbing, Z. Jun, Y. Shichong , Z. Yan, C. Xiaoyun, W. Qiuye, Z. Dazhi, J. Yuanying, S. Qingyan. Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives. European Journal of Medicinal Chemistry, Vol. 46, No.7, pp. 3142-3148, 2011.
  • [4] J. Alessandro K., F.Vitor F., S. Thiago M.L., F. Gabrielle G. de Souza, M. Viviane, A. Juliana L., S. Maria C.B.V. de, C.Anna C. Synthesis and anti-HSV-1 activity of new 1,2,3-triazole derivatives. Bioorganic & Medicinal Chemistry, Vol. 19, No. 6, 15, pp. 1860-1865, 2011.
  • [5] S.Yuan, Z. Cheng-He. Synthesis and evaluation of a class of new coumarin triazole derivatives as potential antimicrobial agents. Bioorganic & Medicinal Chemistry Letters, Vol. 21, No. 3, 1, pp. 956-960 , 2011.
  • [6] C. Xiufang, C. Changshui, L. Wenchang L, K. Shaoyong. Chiral ȕ-arylalkyl-1H-1,2,4-triazoles as demethylase inhibitors: Biological evaluation and its stereoselective interaction with sterol 14Įdemethylase from Penicillium digitatum. Pesticide Biochemistry and Physiology, Vol. 99, No. 2, pp. 189-193 , 2011.
  • [7] H. Sanne A. B., P. Tessa E., B. Evert-Jan van den, V. Leo T.M. van der, P. Aldert H. Chemical class-specific gene expression changes in the zebrafish embryo after exposure to glycol ether alkoxy acids and 1,2,4-triazole antifungals. Reproductive Toxicology, In Press, Corrected Proof, Available online , 2011.
  • [8] J. Yongwei, Z. Jun, C. Yongbing, C. Xiaoyun, Z. Yan, W. Qiuye, Z. Dazhi, J. Yuanying, S. Qingyan. Synthesis, in vitro evaluation and molecular docking studies of new triazole derivatives
  • as antifungal agents. Bioorganic & Medicinal Chemistry Letters, In Press, Accepted Manuscript, Available online, 2011.
  • [9] P. David, F. Prabhavathi. Synthesis and antibacterial activity of novel 4-aryl-[1,2,3]-triazole containing macrolides. Bioorganic & Medicinal Chemistry Letters, Vol. 21, No. 1, pp. 510-513, 1 , 2011.
  • [10] K.D. Thomas, A. Airody Vasudeva, C. Imran H., E. Sumesh, P. Nishith K. New quinolin-4-yl1,2,3-triazoles carrying amides, sulphonamides and amidopiperazines as potential antitubercular agents. European Journal of Medicinal Chemistry, Vol. 46, No. 6, pp. 2503-2512, 2011.
  • [11] R.D. Hunashal, P.M. Ronad, V.S. Maddi, D. Satyanarayana, M.A. Kamadod. Synthesis, antiinflammatory and analgesic activity of 2-[4-(substituted benzylideneamino)-5-(substituted phenoxymethyl)-4H-1,2,4-triazol-3-yl thio] acetic acid derivatives. Arabian Journal of Chemistry, In Press, Corrected Proof, Available online, 2011.
  • [12] K. Ahmed, S. Prabhakar, M. Janaki Ramaiah, P. Venkat Reddy, Ch. Ratna Reddy, A. Mallareddy, S. Nagula, T. Lakshmi Narayan Reddy, S.N.C.V.L. Pushpavalli, P. Manika. Synthesis and anticancer activity of chalcone-pyrrolobenzodiazepine conjugates linked via 1,2,3-triazole ring side-armed with alkane spacers. European Journal of Medicinal Chemistry, In Press, Corrected Proof, Available online, 2011.
  • [13] R. Yi-Bin, M. Stéphane, X. Juan. Highly selective fluorescent and colorimetric sensor for Hg2+ based on triazole-linked NBD. Dyes and Pigments, Vol. 90, No.3, pp. 239-244, 2011.
  • [14] Z. Yin-Jie, H. Xiao-Peng, H. Min, L. Zhen, S. Xiao-Xin, C. Guo-Rong. Highly optically selective and electrochemically active chemosensor for copper (II) based on triazole-linked glucosyl anthraquinone. Dyes and Pigments, Vol. 88, No.3, pp. 391-395, 2011.
  • [15] P. Monika, K. Zbigniew, W. Waldemar, K. Agnieszka A., M. Dariusz. Experimental and theoretical investigations on the keto–enol tautomerism of 4-substituted 3-[1-methylpyrrol-2yl)methyl]-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Journal of Molecular Structure, Vol. 994, No.1-3, pp.313-320, 2011.
  • [16] S. Antonio, V. Carmen, C. Ana María García, G. Fernando, P. Paolo, A. Ibon, E. José. Synthesis of [1,2,4]-triazolo[1,5-a]pyrimidines by Dimroth rearrangement of [1,2,4]-triazolo[4,3a]pyrimidines: A theoretical and NMR study. Journal of Molecular Structure, Vol. 987, No. 1-3, pp. 13-24, 2011.
  • [17] R. Luke, C. David J., E. Paul I.P. Theoretical investigation of the scope of sequential ligand tuning using a bifunctional scorpionate tris(1,2,4-triazolyl)borate-based architecture. Journal of Organometallic Chemistry, Vol. 696, No. 13, pp. 2580-2583, 2011.
  • [18] S. Fidan, "1,2,4-Triazol ve Türevlerinin Kuantum Kimyasal øncelenmesi", Yüksek Lisans Tezi, Eskiúehir Osmangazi Üniversitesi, Fen Bilimleri Enstitüsü, ss. 49–73, 2007.
  • [19] C. Ö÷retir, Y.G. Sõdõr, ø. Sõdõr, E. Taúal, Quantum chemical studies on tautomerism and basicity behavior of 1,2,4-triazole derivatives, Türk. J. Chem., Vol.34 pp. 977-988, 2010.
  • [20] J. Katalan, J.Luis, M.Abboud, J. Elguero, Basicity and Acidity of Azoles, Academic Press, New York, Vol. 41, pp. 259, 1987.
  • [21] L.A. Curtiss and M.S. Gordon, “Computational Materials Chemistry Methods and Applicatõons” Kluwer Academic Publishers New York, Boston, Dordrecht, London, Moscow, 2005.
  • [22] T. Carl and S. Donald, “Electronic Structure Modeling, Connections Between Theory and Software” CRC Press Taylor & Francis Group, Boca Raton London New York, 2008.
  • [23] CAChe Worksystem Pro Version 6.1 Fujitsu Limited, Life Science & Material Science Division 93, Nakase 1-Chome Mihama-ku, Chiba City Chiba 261-8588 Japan, 2000-2003.
  • [24] CS Chemoffice Pro for Microsoft Windows, Cambridge Scientific Computing Inc., 875 Massachusetts Avenue, Suite 61, Cambridge MA 2139, USA.

1,2,4-TRİAZOL VE TÜREVLERİNİN pKa’LARININ TEORİK HESAPLANMASI

Yıl 2011, Cilt: 24 Sayı: 2, 51 - 70, 30.12.2011

Öz

Bu çalışamada sekiz adet 1,2,4-triazol türevi asitlik sabitleri (pKa), molekülleri karakterize eden fizikokimyasal parametreler, yarı deneysel kuantum kimyasal metotlar (AM1, PM3, PM5) kullanılarak CAChe 6.0 programı ile hesaplanmıştır. Teorik olarak bulunan pKa de÷erleriyle, deneysel veriler arasındaki paralellik araştırılmıştır. Yapılan hesaplamalar sonucunda termokinetik parametrelerle yapılan hesaplamaların uygun sonuç verdiği bulunmuştur

Kaynakça

  • [1] B. Modzelewska-Banachiewicz, J. Banachiewicz, A. Chodkowska, E. Jagiello-Wojtowicz, L. Mazur. Synthesis and Biological Activity of New Derivatives of 3-(3,4-Diaryl-1,2,4-triazole-5-yl) propenoic Acid, Eur. J. Med. Chem. Vol.39, pp. 873–877, 2004.
  • [2] W. Cheng-Xi, D.Xian-Qing, C.Kyu-Yun, S.Zhi-Gang and Q.Zhe-Shan. Synthesis and Anticonvulsant Activity of 1-Formamide-triazolo[4,3-a]quinoline Derivatives, Arch. Pharm. Res. Vol. 33, No 5, pp.655-662, 2010.
  • [3] X. Jianming, C.Yongbing, Z. Jun, Y. Shichong , Z. Yan, C. Xiaoyun, W. Qiuye, Z. Dazhi, J. Yuanying, S. Qingyan. Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives. European Journal of Medicinal Chemistry, Vol. 46, No.7, pp. 3142-3148, 2011.
  • [4] J. Alessandro K., F.Vitor F., S. Thiago M.L., F. Gabrielle G. de Souza, M. Viviane, A. Juliana L., S. Maria C.B.V. de, C.Anna C. Synthesis and anti-HSV-1 activity of new 1,2,3-triazole derivatives. Bioorganic & Medicinal Chemistry, Vol. 19, No. 6, 15, pp. 1860-1865, 2011.
  • [5] S.Yuan, Z. Cheng-He. Synthesis and evaluation of a class of new coumarin triazole derivatives as potential antimicrobial agents. Bioorganic & Medicinal Chemistry Letters, Vol. 21, No. 3, 1, pp. 956-960 , 2011.
  • [6] C. Xiufang, C. Changshui, L. Wenchang L, K. Shaoyong. Chiral ȕ-arylalkyl-1H-1,2,4-triazoles as demethylase inhibitors: Biological evaluation and its stereoselective interaction with sterol 14Įdemethylase from Penicillium digitatum. Pesticide Biochemistry and Physiology, Vol. 99, No. 2, pp. 189-193 , 2011.
  • [7] H. Sanne A. B., P. Tessa E., B. Evert-Jan van den, V. Leo T.M. van der, P. Aldert H. Chemical class-specific gene expression changes in the zebrafish embryo after exposure to glycol ether alkoxy acids and 1,2,4-triazole antifungals. Reproductive Toxicology, In Press, Corrected Proof, Available online , 2011.
  • [8] J. Yongwei, Z. Jun, C. Yongbing, C. Xiaoyun, Z. Yan, W. Qiuye, Z. Dazhi, J. Yuanying, S. Qingyan. Synthesis, in vitro evaluation and molecular docking studies of new triazole derivatives
  • as antifungal agents. Bioorganic & Medicinal Chemistry Letters, In Press, Accepted Manuscript, Available online, 2011.
  • [9] P. David, F. Prabhavathi. Synthesis and antibacterial activity of novel 4-aryl-[1,2,3]-triazole containing macrolides. Bioorganic & Medicinal Chemistry Letters, Vol. 21, No. 1, pp. 510-513, 1 , 2011.
  • [10] K.D. Thomas, A. Airody Vasudeva, C. Imran H., E. Sumesh, P. Nishith K. New quinolin-4-yl1,2,3-triazoles carrying amides, sulphonamides and amidopiperazines as potential antitubercular agents. European Journal of Medicinal Chemistry, Vol. 46, No. 6, pp. 2503-2512, 2011.
  • [11] R.D. Hunashal, P.M. Ronad, V.S. Maddi, D. Satyanarayana, M.A. Kamadod. Synthesis, antiinflammatory and analgesic activity of 2-[4-(substituted benzylideneamino)-5-(substituted phenoxymethyl)-4H-1,2,4-triazol-3-yl thio] acetic acid derivatives. Arabian Journal of Chemistry, In Press, Corrected Proof, Available online, 2011.
  • [12] K. Ahmed, S. Prabhakar, M. Janaki Ramaiah, P. Venkat Reddy, Ch. Ratna Reddy, A. Mallareddy, S. Nagula, T. Lakshmi Narayan Reddy, S.N.C.V.L. Pushpavalli, P. Manika. Synthesis and anticancer activity of chalcone-pyrrolobenzodiazepine conjugates linked via 1,2,3-triazole ring side-armed with alkane spacers. European Journal of Medicinal Chemistry, In Press, Corrected Proof, Available online, 2011.
  • [13] R. Yi-Bin, M. Stéphane, X. Juan. Highly selective fluorescent and colorimetric sensor for Hg2+ based on triazole-linked NBD. Dyes and Pigments, Vol. 90, No.3, pp. 239-244, 2011.
  • [14] Z. Yin-Jie, H. Xiao-Peng, H. Min, L. Zhen, S. Xiao-Xin, C. Guo-Rong. Highly optically selective and electrochemically active chemosensor for copper (II) based on triazole-linked glucosyl anthraquinone. Dyes and Pigments, Vol. 88, No.3, pp. 391-395, 2011.
  • [15] P. Monika, K. Zbigniew, W. Waldemar, K. Agnieszka A., M. Dariusz. Experimental and theoretical investigations on the keto–enol tautomerism of 4-substituted 3-[1-methylpyrrol-2yl)methyl]-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives. Journal of Molecular Structure, Vol. 994, No.1-3, pp.313-320, 2011.
  • [16] S. Antonio, V. Carmen, C. Ana María García, G. Fernando, P. Paolo, A. Ibon, E. José. Synthesis of [1,2,4]-triazolo[1,5-a]pyrimidines by Dimroth rearrangement of [1,2,4]-triazolo[4,3a]pyrimidines: A theoretical and NMR study. Journal of Molecular Structure, Vol. 987, No. 1-3, pp. 13-24, 2011.
  • [17] R. Luke, C. David J., E. Paul I.P. Theoretical investigation of the scope of sequential ligand tuning using a bifunctional scorpionate tris(1,2,4-triazolyl)borate-based architecture. Journal of Organometallic Chemistry, Vol. 696, No. 13, pp. 2580-2583, 2011.
  • [18] S. Fidan, "1,2,4-Triazol ve Türevlerinin Kuantum Kimyasal øncelenmesi", Yüksek Lisans Tezi, Eskiúehir Osmangazi Üniversitesi, Fen Bilimleri Enstitüsü, ss. 49–73, 2007.
  • [19] C. Ö÷retir, Y.G. Sõdõr, ø. Sõdõr, E. Taúal, Quantum chemical studies on tautomerism and basicity behavior of 1,2,4-triazole derivatives, Türk. J. Chem., Vol.34 pp. 977-988, 2010.
  • [20] J. Katalan, J.Luis, M.Abboud, J. Elguero, Basicity and Acidity of Azoles, Academic Press, New York, Vol. 41, pp. 259, 1987.
  • [21] L.A. Curtiss and M.S. Gordon, “Computational Materials Chemistry Methods and Applicatõons” Kluwer Academic Publishers New York, Boston, Dordrecht, London, Moscow, 2005.
  • [22] T. Carl and S. Donald, “Electronic Structure Modeling, Connections Between Theory and Software” CRC Press Taylor & Francis Group, Boca Raton London New York, 2008.
  • [23] CAChe Worksystem Pro Version 6.1 Fujitsu Limited, Life Science & Material Science Division 93, Nakase 1-Chome Mihama-ku, Chiba City Chiba 261-8588 Japan, 2000-2003.
  • [24] CS Chemoffice Pro for Microsoft Windows, Cambridge Scientific Computing Inc., 875 Massachusetts Avenue, Suite 61, Cambridge MA 2139, USA.
Toplam 25 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Kimya Mühendisliği
Bölüm Araştırma Makaleleri
Yazarlar

Erol Açıkkalp Bu kişi benim

Devrim Özöğüt Bu kişi benim

Semih Fidan Bu kişi benim

Yayımlanma Tarihi 30 Aralık 2011
Kabul Tarihi 3 Haziran 2011
Yayımlandığı Sayı Yıl 2011 Cilt: 24 Sayı: 2

Kaynak Göster

APA Açıkkalp, E., Özöğüt, D., & Fidan, S. (2011). 1,2,4-TRİAZOL VE TÜREVLERİNİN pKa’LARININ TEORİK HESAPLANMASI. Eskişehir Osmangazi Üniversitesi Mühendislik Ve Mimarlık Fakültesi Dergisi, 24(2), 51-70.
AMA Açıkkalp E, Özöğüt D, Fidan S. 1,2,4-TRİAZOL VE TÜREVLERİNİN pKa’LARININ TEORİK HESAPLANMASI. ESOGÜ Müh Mim Fak Derg. Aralık 2011;24(2):51-70.
Chicago Açıkkalp, Erol, Devrim Özöğüt, ve Semih Fidan. “1,2,4-TRİAZOL VE TÜREVLERİNİN pKa’LARININ TEORİK HESAPLANMASI”. Eskişehir Osmangazi Üniversitesi Mühendislik Ve Mimarlık Fakültesi Dergisi 24, sy. 2 (Aralık 2011): 51-70.
EndNote Açıkkalp E, Özöğüt D, Fidan S (01 Aralık 2011) 1,2,4-TRİAZOL VE TÜREVLERİNİN pKa’LARININ TEORİK HESAPLANMASI. Eskişehir Osmangazi Üniversitesi Mühendislik ve Mimarlık Fakültesi Dergisi 24 2 51–70.
IEEE E. Açıkkalp, D. Özöğüt, ve S. Fidan, “1,2,4-TRİAZOL VE TÜREVLERİNİN pKa’LARININ TEORİK HESAPLANMASI”, ESOGÜ Müh Mim Fak Derg, c. 24, sy. 2, ss. 51–70, 2011.
ISNAD Açıkkalp, Erol vd. “1,2,4-TRİAZOL VE TÜREVLERİNİN pKa’LARININ TEORİK HESAPLANMASI”. Eskişehir Osmangazi Üniversitesi Mühendislik ve Mimarlık Fakültesi Dergisi 24/2 (Aralık 2011), 51-70.
JAMA Açıkkalp E, Özöğüt D, Fidan S. 1,2,4-TRİAZOL VE TÜREVLERİNİN pKa’LARININ TEORİK HESAPLANMASI. ESOGÜ Müh Mim Fak Derg. 2011;24:51–70.
MLA Açıkkalp, Erol vd. “1,2,4-TRİAZOL VE TÜREVLERİNİN pKa’LARININ TEORİK HESAPLANMASI”. Eskişehir Osmangazi Üniversitesi Mühendislik Ve Mimarlık Fakültesi Dergisi, c. 24, sy. 2, 2011, ss. 51-70.
Vancouver Açıkkalp E, Özöğüt D, Fidan S. 1,2,4-TRİAZOL VE TÜREVLERİNİN pKa’LARININ TEORİK HESAPLANMASI. ESOGÜ Müh Mim Fak Derg. 2011;24(2):51-70.

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