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SPECTROSCOPIC PROPERTIES OF 3-PHENYL-4-(3- CINNAMOYLOXYBENZYLIDENAMINO)-4,5-DIHYDRO-1H-1,2,4-TRIAZOL-5- ONE MOLECULE

Year 2018, Volume: 5 Issue: 2, 65 - 80, 31.12.2018

Abstract

In this paper, synthesized new 3-phenyl-4-(3-cinnamoyloxybenzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one has been optimized using B3LYP/6-31G(d) and HF/6-31G(d) basis set. Starting from this optimized structure with 1H-NMR and 13C-NMR spectral data values according to GIAO method was calculated using the method of Gaussian G09W program package in gas phase and DMSO solvent. Theoretically and experimentally values were plotted according to δ exp=a. δ calc.+ b, Eq. a and b constants regression coefficients with a standard error values were found using the SigmaPlot program. According to obtained conclusions, theoritical and experimental values were seen to be compatible. In the theoretical part of study also, Theoretically calculated IR datas of synthesized new compound was calculated in gas phase by using of 6-31G(d) basis sets of B3LYP and HF methods and are multiplied with appropriate adjustment factors and the data obtained according to B3LYP and HF methods are formed using theoretical infrared spectrum. The identification of calculated IR data was used in veda4f program. Experimentally and theoretically UV-VIS values in ethanol were calculated and compared. Additionally, Titled compounds were found bond angles, bond lengths, dipole moments, the HOMO-LUMO energy and total energy of the molecule with mulliken charges from both methods. 

References

  • Akyıldırım O, Yüksek H, Gökçe H, Bahçeli S, 2012. “The molecular structure, spectroscopic properties and quantum chemical calculations of 1-acetyl-3-methyl-4-[3-methoxy-4-(4-methylbenzoxy)benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones molecule, 2nd International Conference on Computation for Science and Technology, 9-11 temmuz, Niğde.
  • Alkan, M., Yuksek, H., Islamoglu, F., Bahceci, S., Calapoglu, M., Elmastas, M., Aksit, H., Ozdemir, M. (2007). A study on 4-acylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones, Molecules, 12 (8): 1805-1816.
  • Apaydın, F. (1991). Magnetik Rezonans, Hacettepe Üniversitesi, 3, 6-8.
  • Bahçeci Ş, Yüksek H, Ocak Z, Köksal C, Özdemir M, (2002). Synthesis and non-aqueous medium titrations of some new 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives”, Acta Chimica Slovenica, 49; 783-794.
  • Balcı, M., (2011). Nükleer manyetik rezonans spektroskopisi, Üçüncü Basım, ODTÜ Yayıncılık, Ankara.
  • Bartolotti, L. J., Flurchick, K. (1996). An Introduction to Density Functional Theory. Rev. Comp. Chem., 7, 187-216,
  • Bayrak, H., Demirbas, A., Demirbas, N., Karaoglu, S. A. (2010). Cyclization of some carbothioamide derivatives containing antipyrine and triazole moietieses and investigation of their antimicrobial activities, Eur. J. Med. Chem., 45 (11): 4726-4732.
  • Becke, A. D. (1993). Density-functional thermochemistry. III. The role of exact Exchange, The Journal of Chemical Physics. 98, 5648.
  • Beytur M, (2014). Bazı yeni beş üyeli heterosiklik bileşiklerin sentezi ve bazı özelliklerinin incelenmesi, Kafkas Üniversitesi Fen Bilimleri Enstitüsü, Doktora Tezi, 709s.
  • Cheeseman, J. R., Trucks, G. W., Keith, T. A., Frisch, M. J. (1996). A Comparison of Models for Calculating Nuclear Magnetic Resonance Shielding Tensors, The Journal of Chemical Physics. 104. 5497-5509.
  • Eydemir, H. (2010). Biyolojik aktif bazı maddelerin teorik olarak İncelenmesi, Tüksek Lisans Tezi, Osmangazi Üniversitesi Fen Bilimleri Enstitüsü, Eskişehir
  • Fessenden R J, Fessenden JS, (1986). “Organic Chemistry”, Third Edition, Brooks, Cole Publishing Company, California.
  • Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J. A., Vreven, T.Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, N., Staroverov, V. N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M., Knox, J. E., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C. J., Ochterski, W., Martin, L. R., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J., Dapprich, S., Daniels, A. D., Farkas, O., Foresman, J. B., Ortiz, J. V., Cioslowski, J., and Fox, D. J., 2009. Gaussian Inc. (Wallingford, CT).
  • Gans P, (1971). Vibrating Molecules. Chapman and Hall, 18-59 .
  • Gökçe H, Akyıldırım O, Bahçeli S, Yüksek H, Gürsoy Kol O, (2014). The 1-acetyl-3-methyl-4-[3-methoxy-4-(4-methylbenzoxy)benzylidenamino]–4,5–dihydro–1H–1,2,4–triazol–5–one Molecule Investigated by a Joint Spectroscopic and Quantum Chemical Calculations Journal of Molecular Structure, 1056-1057; 273–284.
  • Guzeldemirci, N. U, Kucukbasmaci, O. (2010). Synthesis and antimicrobial activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole moiety, Eur. J. Med. Chem., 45 (1): 63-68
  • Haken, H., Wolf, H. C. (2000). Atom ve Kuantum Fiziği, çeviri: Okur, İ., Değişim yayınları, 345-350.
  • Hohenberg, P., Kohn, W. (1964). Inhomogeneous Electron Gas, Phys. Rev. B, 136, 864.
  • İkizler AA, (1996). Organik Kimyaya Giriş, Dördüncü Baskı, KTÜ Basımevi, Trabzon, Türkiye, 398s.
  • Ikizler, A. A., Ikizler, A. Yüksek, H., Serdar, M. (1998). Antitumor activities of some 4,5-dihydro-1H-1,2,4-triazol-5-ones, Modelling, Masurement & Control C, AMSE press, 57: 25-33.
  • Jamroz, M. H. (2004). Vibrational Energy Distribution Analysis VEDA4 (Warsaw).
  • Jamroz, M. H., Dobrowolski, J. C. (2001). Potential energy distribution (PED) analysis of DFT calculated IR spectra of the most stable Li, Na, and Cu(I) diformate molecules, Journal of Molecular Structure. 475, 565-566.
  • Keith, T., Millam, J. (2009). GaussView, Version 5, R Dennington, Semichem Inc, Shawnee Mission, KS.
  • Kucukguzel, S. G., Rollas, S., Erdeniz, H., Kiraz, M., Ekinci, A. C., Vidin, A. (2000). Synthesis, characterization and pharmacological properties of some 4-arylhydrazono-2-pyrazoline-5-one derivatives obtained from heterocyclic amines, Eur. J. Med. Chem., 35 (7-8): 761-771.
  • Lee, C., Yang, W., Parr, R. G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Physical Review B .37, 785.
  • Merrick JP, Moran D, Radom L, (2007). An Evaluation of Harmonic Vibrational Frequency Scale Factors. Journal of Physical Chemistry A, 111 (45); 11683-11700.
  • Mulliken RS, (1955). Electronic Population Analysis on LCAO–MO Molecular Wave Functions. Journal of Chemical Physics, 23; 1833–1840.
  • Naito, Y., Akahoshi, F., Takeda, S., Okada, T., Kajii, M., Nishimura, H., Sugiura, M., Fukaya, C., Kagitani, Y. (1996). Synthesis and pharmacological activity of triazole derivatives inhibiting eosinophilia, J. Med. Chem., 39 (15): 3019-3029.
  • Parr R., G., Yang W. (1989). Density Functional Theory, Oxford University Press.
  • Rani, A.U.; Sundaraganesan, N.; Kurt, M.; Çınar, M.; Karabacak, M., (2010), Spectrochim. Acta Part A, 75, 1523–1529.
  • Reed, A. E., Curtiss, L. A., Weinhold, F. (1988). Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chemical Reviews. 899.
  • Rostom, S. A. F., Shalaby, M. A., El-Demellawy, M. A. (2003). Polysubstituted pyrazoles, part 5. synthesis of new 1-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylic acid hydrazide analogs and some derived ring systems. a novel class of potential antitumor and anti-hcv agents, Eur. J. Med. Chem., 38 (11-12): 959-974.
  • Sancak, K., Unver, Y., Kazak, C., Dugdu, E., Arslan, B. (2010). Synthesis and characterisations of some new 2,4-dihydro-[1,2,4]-triazol-3-one derivatives and X-ray crystal structures of 4-(3-phenylallylideneamino)-5-thiophen-2-yl-methyl-2,4-dihydro-[1,2,4]triazol-3-one, Turk. J. Chem., 34 (5): 771-780.
  • Silverstein, R. M., Bassler, G. C., Morrill, T. C. (1991). Spectrometric Identification of Organic Compounds (Chichester: John Wiley)
  • Subramanian, N.; Sundaraganesan, N.; Jayabharathi, J., (2010). Spectrochim Acta Part A, 76, 259–269.
  • Takaoka, M., Manabe, S., Yamoto, T., Teranishi, M., Matsunuma, N., Masuda, H., Goto, N. (1994). Comparative-study of goitrogenic actions of 3-substituted 1,2,4-triazoles in rats”, J. Vet. Med. Sci., 56 (2): 341-346.
  • Tao, Y., Han, L., Han, Y., Liu, Z. (2015). Experimental and theoretical studies on the vibrational spectra of trans-3-phenylacryloyl chloride, Spectrochimica Acta Part A. 137, 892-898.
  • Tozkoparan, B., Kupeli, E., Yesilada, E., Ertan, M. (2007). Preparation of 5-aryl-3-alkylthio-1,2,4-triazoles and corresponding sulfones with anti-inflammatory-analgesic activity, Bioorgan. Med. Chem., 15 (4): 1808-1814.
  • Turan-Zitouni, G., Kaplancikli, Z. A., Yildiz, M. T., Chevallet, P., Kaya, D. (2005). Synthesis and antimicrobial activity of 4-phenyl/cyclohexcyl-5-(1-phenoxyethyl)-3-[n-(2-thiazolyl)acetamido]thio-4H-1,2,4-triazole derivatives, Eur. J. Med. Chem., 40 (6): 607-613.
  • Turhan Irak Z, Gümüş S, (2017). Heterotricyclic compounds via click reaction: A computational study. Noble International Journal of Scientific Research, 1(7), 80-89.
  • Wade, Jr. L.G. (2006). Organic Chemistry, 6nd ed.; Pearson Prentice Hall: New Jersey,
  • Wolinski, K., Hilton, J. F. Pulay, P. (1990). Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations, Journal of the American Chemical Society. 112. 8251-8260.
  • Yüksek H, (1992). 3-Alkil(aril)-4-amino-4,5-dihidro-1,2,4-triazol-5-on’ların bazı reaksiyonlarının incelenmesi, KTÜ Fen Bilimleri Enstitüsü, Doktora Tezi.
  • Yüksek H, Demirbaş A, Ikizler A, Johansson CB, Çelik C, Ikizler AA, (1997). “Synthesis and antibacterial activities of some 4,5-dihydro-1H-1,2,4-triazol-5-ones”, Arzneim.-Forsch/Drug Res., 47 (4): 405-409.
  • Yüksek H, Gürsoy Ö, Çakmak İ, Alkan M, 2005a. Synthesis and GIAO NMR Calculation for Some New 4,5-Dihydro-1H-1,2,4-triazol-5-one Derivatives: Comparison of Theoretical and Experimental 1H and 13C Chemical Shifts. Magnetic Resonance in Chemistry, 43; 585-587.
  • Zahid, H. C., Sajjad, H. S., Moulay, H. Y., Taibi, B. H. (2010). Metal based biologically active compounds: Design, synthesis, and antibacterial/antifungal/cytotoxic properties of triazole-derived schiff bases and their oxovanadium(IV) complexes, Eur. J. Med. Chem., 45: 2739-2747.

3-FENİL-4-(3-SİNNAMOİLOKSİBENZİLİDENAMİNO)-4,5-DİHİDRO-1H-1,2,4- TRİAZOL-5-ON MOLEKÜLÜNÜN SPEKTROSKOPİK ÖZELLİKLERİ

Year 2018, Volume: 5 Issue: 2, 65 - 80, 31.12.2018

Abstract

Bu çalışmada, sentezlenmiş yeni 3-fenil-4-(3-sinnamoiloksibenzilidenamino)-4,5- dihidro-1H-1,2,4-triazol-5-on B3LYP/6-31G(d) ve HF/6-31G(d) temel setleri kullanılarak optimize edilmiştir. Bu optimize yapıdan yola çıkılarak 1H-NMR ve 13C-NMR değerleri GIAO metoduna göre Gaussian G09W paket programı kullanılarak gaz fazında ve çözücüsünde hesaplanmıştır. Deneysel ve teorik olarak bulunan değerler δ exp=a. δ calc.+ b eşitliğine göre grafiğe geçirilmiş ve Sigmaplot programı kullanılarak a ve b sabitleri regresyon katsayısı ile standart hata değerleri bulunmuştur. Elde edilen sonuçlara göre teorik verilerin deneysel verilerle uyumlu oldukları görülmüştür. Çalışmanın teorik kısmında ayrıca, sentezlenmiş yeni bileşiğin IR frekans değerleri B3LYP ve HF metodlarının 6-31G(d) temel seti kullanılarak gaz fazında hesaplanmış, elde edilen değerler uygun uyum faktörleri ile çarpılmıştır. Hesaplanan IR verilerinin tanımlanmasında veda4f programından yararlanılmıştır. Deneysel ve teorik olarak UV-VİS değerleri etanollü ortamda hesaplanmış ve mukayese edilmiştir. İlaveten, ilgili bileşiğin bağ açıları, bağ uzunlukları, mulliken yükleri, HOMO-LUMO enerjileri, dipol momentleri ve enerjileri aynı metodlar ve aynı set kullanılarak hesaplanmıştır.

References

  • Akyıldırım O, Yüksek H, Gökçe H, Bahçeli S, 2012. “The molecular structure, spectroscopic properties and quantum chemical calculations of 1-acetyl-3-methyl-4-[3-methoxy-4-(4-methylbenzoxy)benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones molecule, 2nd International Conference on Computation for Science and Technology, 9-11 temmuz, Niğde.
  • Alkan, M., Yuksek, H., Islamoglu, F., Bahceci, S., Calapoglu, M., Elmastas, M., Aksit, H., Ozdemir, M. (2007). A study on 4-acylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones, Molecules, 12 (8): 1805-1816.
  • Apaydın, F. (1991). Magnetik Rezonans, Hacettepe Üniversitesi, 3, 6-8.
  • Bahçeci Ş, Yüksek H, Ocak Z, Köksal C, Özdemir M, (2002). Synthesis and non-aqueous medium titrations of some new 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives”, Acta Chimica Slovenica, 49; 783-794.
  • Balcı, M., (2011). Nükleer manyetik rezonans spektroskopisi, Üçüncü Basım, ODTÜ Yayıncılık, Ankara.
  • Bartolotti, L. J., Flurchick, K. (1996). An Introduction to Density Functional Theory. Rev. Comp. Chem., 7, 187-216,
  • Bayrak, H., Demirbas, A., Demirbas, N., Karaoglu, S. A. (2010). Cyclization of some carbothioamide derivatives containing antipyrine and triazole moietieses and investigation of their antimicrobial activities, Eur. J. Med. Chem., 45 (11): 4726-4732.
  • Becke, A. D. (1993). Density-functional thermochemistry. III. The role of exact Exchange, The Journal of Chemical Physics. 98, 5648.
  • Beytur M, (2014). Bazı yeni beş üyeli heterosiklik bileşiklerin sentezi ve bazı özelliklerinin incelenmesi, Kafkas Üniversitesi Fen Bilimleri Enstitüsü, Doktora Tezi, 709s.
  • Cheeseman, J. R., Trucks, G. W., Keith, T. A., Frisch, M. J. (1996). A Comparison of Models for Calculating Nuclear Magnetic Resonance Shielding Tensors, The Journal of Chemical Physics. 104. 5497-5509.
  • Eydemir, H. (2010). Biyolojik aktif bazı maddelerin teorik olarak İncelenmesi, Tüksek Lisans Tezi, Osmangazi Üniversitesi Fen Bilimleri Enstitüsü, Eskişehir
  • Fessenden R J, Fessenden JS, (1986). “Organic Chemistry”, Third Edition, Brooks, Cole Publishing Company, California.
  • Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J. A., Vreven, T.Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, N., Staroverov, V. N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M., Knox, J. E., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C. J., Ochterski, W., Martin, L. R., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J., Dapprich, S., Daniels, A. D., Farkas, O., Foresman, J. B., Ortiz, J. V., Cioslowski, J., and Fox, D. J., 2009. Gaussian Inc. (Wallingford, CT).
  • Gans P, (1971). Vibrating Molecules. Chapman and Hall, 18-59 .
  • Gökçe H, Akyıldırım O, Bahçeli S, Yüksek H, Gürsoy Kol O, (2014). The 1-acetyl-3-methyl-4-[3-methoxy-4-(4-methylbenzoxy)benzylidenamino]–4,5–dihydro–1H–1,2,4–triazol–5–one Molecule Investigated by a Joint Spectroscopic and Quantum Chemical Calculations Journal of Molecular Structure, 1056-1057; 273–284.
  • Guzeldemirci, N. U, Kucukbasmaci, O. (2010). Synthesis and antimicrobial activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole moiety, Eur. J. Med. Chem., 45 (1): 63-68
  • Haken, H., Wolf, H. C. (2000). Atom ve Kuantum Fiziği, çeviri: Okur, İ., Değişim yayınları, 345-350.
  • Hohenberg, P., Kohn, W. (1964). Inhomogeneous Electron Gas, Phys. Rev. B, 136, 864.
  • İkizler AA, (1996). Organik Kimyaya Giriş, Dördüncü Baskı, KTÜ Basımevi, Trabzon, Türkiye, 398s.
  • Ikizler, A. A., Ikizler, A. Yüksek, H., Serdar, M. (1998). Antitumor activities of some 4,5-dihydro-1H-1,2,4-triazol-5-ones, Modelling, Masurement & Control C, AMSE press, 57: 25-33.
  • Jamroz, M. H. (2004). Vibrational Energy Distribution Analysis VEDA4 (Warsaw).
  • Jamroz, M. H., Dobrowolski, J. C. (2001). Potential energy distribution (PED) analysis of DFT calculated IR spectra of the most stable Li, Na, and Cu(I) diformate molecules, Journal of Molecular Structure. 475, 565-566.
  • Keith, T., Millam, J. (2009). GaussView, Version 5, R Dennington, Semichem Inc, Shawnee Mission, KS.
  • Kucukguzel, S. G., Rollas, S., Erdeniz, H., Kiraz, M., Ekinci, A. C., Vidin, A. (2000). Synthesis, characterization and pharmacological properties of some 4-arylhydrazono-2-pyrazoline-5-one derivatives obtained from heterocyclic amines, Eur. J. Med. Chem., 35 (7-8): 761-771.
  • Lee, C., Yang, W., Parr, R. G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Physical Review B .37, 785.
  • Merrick JP, Moran D, Radom L, (2007). An Evaluation of Harmonic Vibrational Frequency Scale Factors. Journal of Physical Chemistry A, 111 (45); 11683-11700.
  • Mulliken RS, (1955). Electronic Population Analysis on LCAO–MO Molecular Wave Functions. Journal of Chemical Physics, 23; 1833–1840.
  • Naito, Y., Akahoshi, F., Takeda, S., Okada, T., Kajii, M., Nishimura, H., Sugiura, M., Fukaya, C., Kagitani, Y. (1996). Synthesis and pharmacological activity of triazole derivatives inhibiting eosinophilia, J. Med. Chem., 39 (15): 3019-3029.
  • Parr R., G., Yang W. (1989). Density Functional Theory, Oxford University Press.
  • Rani, A.U.; Sundaraganesan, N.; Kurt, M.; Çınar, M.; Karabacak, M., (2010), Spectrochim. Acta Part A, 75, 1523–1529.
  • Reed, A. E., Curtiss, L. A., Weinhold, F. (1988). Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chemical Reviews. 899.
  • Rostom, S. A. F., Shalaby, M. A., El-Demellawy, M. A. (2003). Polysubstituted pyrazoles, part 5. synthesis of new 1-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylic acid hydrazide analogs and some derived ring systems. a novel class of potential antitumor and anti-hcv agents, Eur. J. Med. Chem., 38 (11-12): 959-974.
  • Sancak, K., Unver, Y., Kazak, C., Dugdu, E., Arslan, B. (2010). Synthesis and characterisations of some new 2,4-dihydro-[1,2,4]-triazol-3-one derivatives and X-ray crystal structures of 4-(3-phenylallylideneamino)-5-thiophen-2-yl-methyl-2,4-dihydro-[1,2,4]triazol-3-one, Turk. J. Chem., 34 (5): 771-780.
  • Silverstein, R. M., Bassler, G. C., Morrill, T. C. (1991). Spectrometric Identification of Organic Compounds (Chichester: John Wiley)
  • Subramanian, N.; Sundaraganesan, N.; Jayabharathi, J., (2010). Spectrochim Acta Part A, 76, 259–269.
  • Takaoka, M., Manabe, S., Yamoto, T., Teranishi, M., Matsunuma, N., Masuda, H., Goto, N. (1994). Comparative-study of goitrogenic actions of 3-substituted 1,2,4-triazoles in rats”, J. Vet. Med. Sci., 56 (2): 341-346.
  • Tao, Y., Han, L., Han, Y., Liu, Z. (2015). Experimental and theoretical studies on the vibrational spectra of trans-3-phenylacryloyl chloride, Spectrochimica Acta Part A. 137, 892-898.
  • Tozkoparan, B., Kupeli, E., Yesilada, E., Ertan, M. (2007). Preparation of 5-aryl-3-alkylthio-1,2,4-triazoles and corresponding sulfones with anti-inflammatory-analgesic activity, Bioorgan. Med. Chem., 15 (4): 1808-1814.
  • Turan-Zitouni, G., Kaplancikli, Z. A., Yildiz, M. T., Chevallet, P., Kaya, D. (2005). Synthesis and antimicrobial activity of 4-phenyl/cyclohexcyl-5-(1-phenoxyethyl)-3-[n-(2-thiazolyl)acetamido]thio-4H-1,2,4-triazole derivatives, Eur. J. Med. Chem., 40 (6): 607-613.
  • Turhan Irak Z, Gümüş S, (2017). Heterotricyclic compounds via click reaction: A computational study. Noble International Journal of Scientific Research, 1(7), 80-89.
  • Wade, Jr. L.G. (2006). Organic Chemistry, 6nd ed.; Pearson Prentice Hall: New Jersey,
  • Wolinski, K., Hilton, J. F. Pulay, P. (1990). Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations, Journal of the American Chemical Society. 112. 8251-8260.
  • Yüksek H, (1992). 3-Alkil(aril)-4-amino-4,5-dihidro-1,2,4-triazol-5-on’ların bazı reaksiyonlarının incelenmesi, KTÜ Fen Bilimleri Enstitüsü, Doktora Tezi.
  • Yüksek H, Demirbaş A, Ikizler A, Johansson CB, Çelik C, Ikizler AA, (1997). “Synthesis and antibacterial activities of some 4,5-dihydro-1H-1,2,4-triazol-5-ones”, Arzneim.-Forsch/Drug Res., 47 (4): 405-409.
  • Yüksek H, Gürsoy Ö, Çakmak İ, Alkan M, 2005a. Synthesis and GIAO NMR Calculation for Some New 4,5-Dihydro-1H-1,2,4-triazol-5-one Derivatives: Comparison of Theoretical and Experimental 1H and 13C Chemical Shifts. Magnetic Resonance in Chemistry, 43; 585-587.
  • Zahid, H. C., Sajjad, H. S., Moulay, H. Y., Taibi, B. H. (2010). Metal based biologically active compounds: Design, synthesis, and antibacterial/antifungal/cytotoxic properties of triazole-derived schiff bases and their oxovanadium(IV) complexes, Eur. J. Med. Chem., 45: 2739-2747.
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Details

Primary Language Turkish
Journal Section Articles
Authors

Murat Beytur

Haydar Yüksek This is me 0000-0003-1289-1800

Publication Date December 31, 2018
Submission Date December 30, 2018
Acceptance Date December 31, 2018
Published in Issue Year 2018 Volume: 5 Issue: 2

Cite

APA Beytur, M., & Yüksek, H. (2018). 3-FENİL-4-(3-SİNNAMOİLOKSİBENZİLİDENAMİNO)-4,5-DİHİDRO-1H-1,2,4- TRİAZOL-5-ON MOLEKÜLÜNÜN SPEKTROSKOPİK ÖZELLİKLERİ. Caucasian Journal of Science, 5(2), 65-80.

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