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Yıl 2019, Cilt: 6 Sayı: 2, 200 - 215, 27.12.2019

Öz

Destekleyen Kurum

Bu Tez Çalışması Kafkas Üniversitesi Araştırma Fonu Tarafından Desteklenmiştir

Proje Numarası

2014-FEF-24

Kaynakça

  • 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.
  • Anderson, R. J., Bendell, D. J., Groundwater, P. W. (2004). Organic Spectroscopic Analysis, The Royal Society of Chemistry: Sanderland, UK.
  • Avcı, D., Atalay, Y. (2008). Theoretical analysis of vibrational spectra and scaling‐factor of 2‐aryl‐1,3,4‐oxadiazole derivatives, International Journal of Quantum Chemistry, 109, 328-341.
  • Bahçeci, Ş., Yüksek, H., Ocak, Z., Köksal, C., Ozdemir, 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.
  • 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, European Journal of Medicinal Chemistry, 45 (11), 4726-4732.
  • Becke, A. D. (1993). Density functional thermochemistry. III. The role of exact Exchange, The Journal of Chemical Physics, 98, 5648-5652.
  • Beytur, M., Turhan Irak, Z., Manap, S., and Yüksek, H. (2019). Synthesis, Characterization and Theoretical Determination of Corrosion Inhibitor Activities of Some New 4,5-Dihydro-1H-1,2,4-Triazol-5-one Derivatives, Heliyon, 5 (6), e01809, 1-8.
  • Çiftçi, E., Beytur, M., Calapoğlu, M., Gürsoy Kol, Ö., Alkan, M., Toğay, V. A., Manap, S., & Yüksek, H. (2018). Synthesis, Characterization, Antioxidant and Antimicrobial Activities and DNA Damage of Some Novel 2-[3-alkyl (aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-phenoxyacetic acids in Human Lymphocytes, Research Journal of Pharmaceutical, Biological and Chemical Sciences, 9 (5), 1760-1771.
  • Dennington, R., Keith, T., Millam, J. (2009). GaussView, Version 5, Semichem Inc., Shawnee Mission KS.
  • Frisch, M. J., Trucks, G., 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., Jr. Vreven, T., 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., Ochterski, J. 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. & Fox, D. J. (2009). Gaussian Inc., Wallingford, CT.
  • Fukui, K. (1982). Role of Frontier Orbitals in Chemical Reactions. Science, 218, 747-754.
  • Gürsoy Kol, Ö., Yüksek, H. (2010). Synthesis and invitro antioxidant evaluation of some novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, E-Journal of Chemistry, 7 (1), 123-136.
  • 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, European Journal of Medicinal Chemistry, 45 (1), 63-68.
  • Hashem, A. I., Youssef, A. S. A., Kandeel, K. A., Abou-Elmalgd, W. S. I. (2007). Conversion of some 2(3H)-furanones bearing a pyrazolyl group into other heterocyclic systems with a study of their antiviral activity, European Journal of Medicinal Chemistry, 42 (7), 934-939.
  • Ikizler, A. A., Un, R. (1979). Reactions of ester ethoxycarbonylhydrazones with some amine type compounds. Chim. Acta Turc. 7, 269–290. [Chem. Abstr.1991, 94, 15645d].
  • İkizler, A. A., Yüksek, H. (1993). Acetylation of 4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones, Organic Preparations and Procedures International, 25, 99-105.
  • Lee, S. Y. (1998). Molecular Structure and Vibrational Spectra of Biphenyl in the Ground and the lowest Triplet States. Density Functional Theory Study, Bulletin of the Korean Chemical Society, 19 (1), 93-98.
  • Mulliken, R. S. (1955). Electronic Population Analysis on LCAO-MO Molecular Wave Functions. I, American Institute of Physics, 23, 1833-1840.
  • Pir, H., Günay, N., Tamer, Ö., Avcı, D., Atalay, Y. (2013). Theoretical investigation of 5-(2-Acetoxyethyl)-6-methylpyrimidin-2, 4-dione: Conformational study, NBO and NLO analysis, molecular structure and NMR spectra, Spectrochimica Acta. Part A, 112, 331-342.
  • Rani, A. U., Sundaraganesan, N., Kurt, M., Çınar, M., Karabacak, M. (2010). FT-IR, FT-Raman, NMR spectra and DFT calculations on 4-chloro-N-methylaniline, Spectrochimica Acta. Part A, 75, 1523-1529.
  • 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, Turkish Journal of Chemistry, 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). Molecular structure, spectroscopic (FT-IR, FT-Raman, NMR, UV) studies and first-order molecular hyperpolarizabilities of 1,2-bis(3-methoxy-4-hydroxybenzylidene)hydrazine by density functional method, Spectrochim Acta Part A, 76, 259-269.
  • Tereci, H., Askeroğlu, İ., Akdemir, N., Uçar, İ., Büyükgüngör, O. (2012). Combined experimental and theoretical approaches to the molecular structure of 4-(1-formylnaphthalen-2-yloxy)phthalonitrile, Spectrochimica Acta. Part A, 96, 569-577.
  • 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, Bioorganic & Medicinal Chemistry, 15 (4), 1808-1814.
  • Turhan Irak, Z. & Beytur, M. (2019). 4-Benzilidenamino-4,5-dihidro-1H-1,2,4-triazol-5-on Türevlerinin Antioksidan Aktivitelerinin Teorik Olarak İncelenmesi, Iğdır University Journal of the Institute of Science and Technology, 9 (1), 512-521.
  • Turhan, Irak Z., Gümüş, S. (2017). Heterotricyclic compounds via click reaction: A computational study. Noble International Journal of Scientific Research, 1(7), 80-89.
  • Vasavado, J. A., Parekh, H. H. (2003). Synthesis and antimicrobial screening of cyclohexenones and oxazines, Journal of the Indian chemical society, 80, 55-56.
  • Vosko, S. H., Wilk, L., Nusair, M. (1980). Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis, Canadian Journal of Physics. 58, 1200.
  • Yüksek, H. (1992). 3-Alkil(aril)-4-amino-4,5-dihidro-1,2,4-triazol-5-on’ların bazı reaksiyonlarının incelenmesi, Doktora Tezi, KTÜ Fen Bilimleri Enstitüsü, Trabzon.
  • Yüksek, H., Üçüncü, O., Alkan, M., Ocak, Z., Bahçeci, Ş., Özdemir, M. (2005a). Synthesis and Determination of pKa Values of Some New 3,4-Disubstituted-4,5-Dihydro-1H-1,2,4-triazol-5-one Derivatives in Non-aqueous Solvents, Molecules 10, 961-970.
  • Yüksek, H., Gursoy, O., Cakmak, I., Alkan, M. (2005c). 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 (7), 585-587.
  • Yüksek, H., Kolaylı, S., Küçük, M., Yüksek, M. Ö., Ocak, U., Şahinbaş, E., Sivrikaya, E., Ocak, M. (2006). Synthesis and Antioxidant Activities of Some 4-Benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives, Indian Journal of Chemistry - Section B, 45B, 715-718.
  • Wade, L.G. (2006). Organic Chemistry, 6nd ed. Pearson Prentice Hall: New Jersey.

The Investigation of Molecular and Spectroscopic Properties of 3-Ethyl-4-(4- cinnamoyloxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one Compound Using B3LYP and HF Basis Sets

Yıl 2019, Cilt: 6 Sayı: 2, 200 - 215, 27.12.2019

Öz

In this study, we reported a combined experimental and theoretical study on 3-ethyl-4-(4-cinnamoyloxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one compound. The title compound was prepared and characterized by 1H and 13C NMR and FT-IR spectra. The molecular geometry, gauge including atomic orbital (GIAO), Experimental and theoretical values were inserted into the graphic according to equitation of δexp=a+b. δ calc. The standard error values were found via Sigma Plot program with regression coefficient of a and b constants. Also, the calculated IR data of compound were calculated in gas phase by using of 6-31G(d) basis set of B3LYP method and are multiplied with appropriate adjustment factors. Theoretical infrared spectrums are formed from the data obtained according to B3LYP method. In the identification of calculated IR data was used the veda4f program. 1H and 13C NMR chemical shift values, vibrational frequencies and HOMO-LUMO analyses properties, Mulliken’s atomic charges, dipole moment and total energy of the title compound in the ground state were investigated by using Hartree-Fock (HF) and density functional theory (DFT/B3LYP) methods with 6-31G(d) basic set. Obtained results indicate that there is a good agreement between the experimental and theoretical data.

Proje Numarası

2014-FEF-24

Kaynakça

  • 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.
  • Anderson, R. J., Bendell, D. J., Groundwater, P. W. (2004). Organic Spectroscopic Analysis, The Royal Society of Chemistry: Sanderland, UK.
  • Avcı, D., Atalay, Y. (2008). Theoretical analysis of vibrational spectra and scaling‐factor of 2‐aryl‐1,3,4‐oxadiazole derivatives, International Journal of Quantum Chemistry, 109, 328-341.
  • Bahçeci, Ş., Yüksek, H., Ocak, Z., Köksal, C., Ozdemir, 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.
  • 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, European Journal of Medicinal Chemistry, 45 (11), 4726-4732.
  • Becke, A. D. (1993). Density functional thermochemistry. III. The role of exact Exchange, The Journal of Chemical Physics, 98, 5648-5652.
  • Beytur, M., Turhan Irak, Z., Manap, S., and Yüksek, H. (2019). Synthesis, Characterization and Theoretical Determination of Corrosion Inhibitor Activities of Some New 4,5-Dihydro-1H-1,2,4-Triazol-5-one Derivatives, Heliyon, 5 (6), e01809, 1-8.
  • Çiftçi, E., Beytur, M., Calapoğlu, M., Gürsoy Kol, Ö., Alkan, M., Toğay, V. A., Manap, S., & Yüksek, H. (2018). Synthesis, Characterization, Antioxidant and Antimicrobial Activities and DNA Damage of Some Novel 2-[3-alkyl (aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-phenoxyacetic acids in Human Lymphocytes, Research Journal of Pharmaceutical, Biological and Chemical Sciences, 9 (5), 1760-1771.
  • Dennington, R., Keith, T., Millam, J. (2009). GaussView, Version 5, Semichem Inc., Shawnee Mission KS.
  • Frisch, M. J., Trucks, G., 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., Jr. Vreven, T., 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., Ochterski, J. 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. & Fox, D. J. (2009). Gaussian Inc., Wallingford, CT.
  • Fukui, K. (1982). Role of Frontier Orbitals in Chemical Reactions. Science, 218, 747-754.
  • Gürsoy Kol, Ö., Yüksek, H. (2010). Synthesis and invitro antioxidant evaluation of some novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, E-Journal of Chemistry, 7 (1), 123-136.
  • 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, European Journal of Medicinal Chemistry, 45 (1), 63-68.
  • Hashem, A. I., Youssef, A. S. A., Kandeel, K. A., Abou-Elmalgd, W. S. I. (2007). Conversion of some 2(3H)-furanones bearing a pyrazolyl group into other heterocyclic systems with a study of their antiviral activity, European Journal of Medicinal Chemistry, 42 (7), 934-939.
  • Ikizler, A. A., Un, R. (1979). Reactions of ester ethoxycarbonylhydrazones with some amine type compounds. Chim. Acta Turc. 7, 269–290. [Chem. Abstr.1991, 94, 15645d].
  • İkizler, A. A., Yüksek, H. (1993). Acetylation of 4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones, Organic Preparations and Procedures International, 25, 99-105.
  • Lee, S. Y. (1998). Molecular Structure and Vibrational Spectra of Biphenyl in the Ground and the lowest Triplet States. Density Functional Theory Study, Bulletin of the Korean Chemical Society, 19 (1), 93-98.
  • Mulliken, R. S. (1955). Electronic Population Analysis on LCAO-MO Molecular Wave Functions. I, American Institute of Physics, 23, 1833-1840.
  • Pir, H., Günay, N., Tamer, Ö., Avcı, D., Atalay, Y. (2013). Theoretical investigation of 5-(2-Acetoxyethyl)-6-methylpyrimidin-2, 4-dione: Conformational study, NBO and NLO analysis, molecular structure and NMR spectra, Spectrochimica Acta. Part A, 112, 331-342.
  • Rani, A. U., Sundaraganesan, N., Kurt, M., Çınar, M., Karabacak, M. (2010). FT-IR, FT-Raman, NMR spectra and DFT calculations on 4-chloro-N-methylaniline, Spectrochimica Acta. Part A, 75, 1523-1529.
  • 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, Turkish Journal of Chemistry, 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). Molecular structure, spectroscopic (FT-IR, FT-Raman, NMR, UV) studies and first-order molecular hyperpolarizabilities of 1,2-bis(3-methoxy-4-hydroxybenzylidene)hydrazine by density functional method, Spectrochim Acta Part A, 76, 259-269.
  • Tereci, H., Askeroğlu, İ., Akdemir, N., Uçar, İ., Büyükgüngör, O. (2012). Combined experimental and theoretical approaches to the molecular structure of 4-(1-formylnaphthalen-2-yloxy)phthalonitrile, Spectrochimica Acta. Part A, 96, 569-577.
  • 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, Bioorganic & Medicinal Chemistry, 15 (4), 1808-1814.
  • Turhan Irak, Z. & Beytur, M. (2019). 4-Benzilidenamino-4,5-dihidro-1H-1,2,4-triazol-5-on Türevlerinin Antioksidan Aktivitelerinin Teorik Olarak İncelenmesi, Iğdır University Journal of the Institute of Science and Technology, 9 (1), 512-521.
  • Turhan, Irak Z., Gümüş, S. (2017). Heterotricyclic compounds via click reaction: A computational study. Noble International Journal of Scientific Research, 1(7), 80-89.
  • Vasavado, J. A., Parekh, H. H. (2003). Synthesis and antimicrobial screening of cyclohexenones and oxazines, Journal of the Indian chemical society, 80, 55-56.
  • Vosko, S. H., Wilk, L., Nusair, M. (1980). Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis, Canadian Journal of Physics. 58, 1200.
  • Yüksek, H. (1992). 3-Alkil(aril)-4-amino-4,5-dihidro-1,2,4-triazol-5-on’ların bazı reaksiyonlarının incelenmesi, Doktora Tezi, KTÜ Fen Bilimleri Enstitüsü, Trabzon.
  • Yüksek, H., Üçüncü, O., Alkan, M., Ocak, Z., Bahçeci, Ş., Özdemir, M. (2005a). Synthesis and Determination of pKa Values of Some New 3,4-Disubstituted-4,5-Dihydro-1H-1,2,4-triazol-5-one Derivatives in Non-aqueous Solvents, Molecules 10, 961-970.
  • Yüksek, H., Gursoy, O., Cakmak, I., Alkan, M. (2005c). 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 (7), 585-587.
  • Yüksek, H., Kolaylı, S., Küçük, M., Yüksek, M. Ö., Ocak, U., Şahinbaş, E., Sivrikaya, E., Ocak, M. (2006). Synthesis and Antioxidant Activities of Some 4-Benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives, Indian Journal of Chemistry - Section B, 45B, 715-718.
  • Wade, L.G. (2006). Organic Chemistry, 6nd ed. Pearson Prentice Hall: New Jersey.
Toplam 35 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Çevre Bilimleri
Bölüm Makaleler
Yazarlar

Murat Beytur 0000-0002-7098-5592

Haydar Yüksek 0000-0003-1289-1800

Proje Numarası 2014-FEF-24
Yayımlanma Tarihi 27 Aralık 2019
Gönderilme Tarihi 15 Aralık 2019
Kabul Tarihi 27 Aralık 2019
Yayımlandığı Sayı Yıl 2019 Cilt: 6 Sayı: 2

Kaynak Göster

APA Beytur, M., & Yüksek, H. (2019). The Investigation of Molecular and Spectroscopic Properties of 3-Ethyl-4-(4- cinnamoyloxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one Compound Using B3LYP and HF Basis Sets. Caucasian Journal of Science, 6(2), 200-215.

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