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The Investigation of Spectroscopic and Electronic Properties of 3-Ethyl-4-(4-cinnamoyloxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one Compound Using Density Functional Theory and Hartree-Fock Basis Sets

Year 2021, Volume: 15 , 79 - 87, 31.12.2021

Murat Beytur Haydar Yuksek

https://doi.org/10.55549/epstem.1055607

Abstract

In this study, we reported a combined experimental and theoretical study on 3-n-propyl-4-(3-cinnamoyloxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one compound. The title compound was prepared and characterized by Uv-Vis, FT-IR spectra, 1H and 13C NMR. UV-visible absorption spectra and the stimulation contributions in UV-visible transitions were obtained with TD-DFT/B3LYP and TD-FF methods and 6-311G(d) polarizer set based on optimized structure. Calculated absorption wavelengths (λ), oscillator power (f) and excitation energies were compared with experimental values. The calculated IR data of compound were calculated in gas phase by using of 6-31G(d) basis set of B3LYP and HF methods and are multiplied with appropriate scala 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. 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 SigmaPlot program with regression coefficient of a and b constants. Obtained results indicate that there is a good agreement between the experimental and theoretical data. Also, 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.

Keywords

1 2 4-Triazol-5-one DFT Hartree-Fock HOMO-LUMO Gaussian G09

References

  • Aktaş-Yokuş, Ö., Yüksek, H., Manap, S., Aytemiz, F., Alkan, M., Beytur, M., & Gürsoy-Kol, Ö. (2017). In-vitro biological activity of some new 1, 2, 4-triazole derivatives with their potentiometric titrations. Bulgarian Chemical Communications, 49(1), 98-106.
  • Alkan, M., Yüksek, H., İslamoğlu, F., Bahçeci, S., Calapoğlu, M., Elmastaş, M., ... & Özdemir, M. (2007). A Study on 4-Acylamino-4, 5-dihydro-1H-1, 2, 4-triazol-5-ones. Molecules, 12(8), 1805-1816.
  • Avcı, D., & Atalay, Y. (2009). Theoretical analysis of vibrational spectra and scaling‐factor of 2‐aryl‐1, 3, 4‐oxadiazole derivatives. International Journal of Quantum Chemistry, 109(2), 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.
  • Bahçeci, Ş. Yıldırım, N. Alkan, M. Gürsoy-Kol Ö., Manap, S., Beytur, M. & Yüksek, H. (2017). Investigation of Antioxidant, Biological and Acidic Properties of New 3-Alkyl(Aryl)-4-(3-acetoxy-4-methoxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones, The Pharmaceutical and Chemical Journal, 4(4), 91-101.
  • Bahçeci, Ş., Yıldırım, N., Gürsoy-Kol, Ö., Manap, S., Beytur, M., & Yüksek, H. (2016). Synthesis, characterization and antioxidant properties of new 3-alkyl (aryl)-4-(3-hydroxy-4-methoxybenzylidenamino)-4, 5-dihydro-1H-1, 2, 4-triazol-5-ones. Rasayan Journal of Chemistry, 9(3), 494-501.
  • Bayrak, H., Demirbas, A., Demirbas, N., & Karaoglu, S. A. (2010). Cyclization of some carbothioamide derivatives containing antipyrine and triazole moieties and investigation of their antimicrobial Beytur, M. (2020).
  • Fabrication of platinum nanoparticle/boron nitride quantum dots/6-methyl-2-(3-hydroxy-4-methoxybenzylidenamino)-benzothiazole (ils) nanocomposite for electrocatalytic oxidation of methanol. Journal of the Chilean Chemical Society, 65(3), 4929-4933.
  • Beytur, M., & Avinca, I. (2021). Molecular, Electronic, Nonlinear Optical and Spectroscopic Analysis of Heterocyclic 3-Substituted-4-(3-methyl-2-thienylmethyleneamino)-4, 5-dihydro-1H-1, 2, 4-triazol-5-ones: Experiment and DFT Calculations. Heterocyclic Communications, 27(1), 1-16.
  • Beytur, M., Irak, Z. T., Manap, S., & 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.
  • Boy, S. Türkan, F. Beytur, M. Aras, A. Akyıldırım O., Sedef Karaman, H., & Yüksek, H. (2021). Synthesis, design, and assessment of novel morpholine-derived Mannich bases as multifunctional agents for the potential enzyme inhibitory properties including docking study, Bioorganic Chemistry. 107, 104524.
  • 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. Shawnee Mission.
  • Fukui, K. (1982). Role of frontier orbitals in chemical reactions. science, 218(4574), 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.
  • Güzeldemirci 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.
  • Koç, E., Yüksek, H., Beytur, M., Akyıldırım, O., Akçay, M., & Beytur, C. (2020). Heterosiklik 4, 5-dihidro-1H-1, 2, 4-triazol-5-on türevinin antioksidan özelliğinin erkek ratlarda (wistar albino) in vivo olarak belirlenmesi. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, 9(2), 542-548.
  • 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. The Journal of Chemical Physics, 23(10), 1833-1840.
  • Rani, A. U., Sundaraganesan, N., Kurt, M., Cinar, M., & Karabacak, M. (2010). FT-IR, FT-Raman, NMR spectra and DFT calculations on 4-chloro-N-methylaniline. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 75(5), 1523-1529.
  • Silverstein, R. M., & Bassler, G. C. (1962). Spectrometric identification of organic compounds. Journal of Chemical Education, 39(11), 546.
  • 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. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 76(2), 259-269.
  • 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 incelenmesi. 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.
  • Uğurlu, G., & Beytur, M. (2020). Theoretical studies on the structural, vibrational, conformational analysis and nonlinear optic (NLO) property of 4-(Methoxycarbonyl) phenylboronic acid. Indian Journal of Chemistry-Section A, 59(10), 1504-1512.
  • Vasavada, J. A., & Parekh, H. H. (2003). Synthesis and antimicrobial screening of cyclohexenones and oxazines. ChemInform, 34(39), 55-56.
  • Wade, L.G. (2006). Organic chemistry (6nd ed). Pearson Prentice Hall.
  • 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, 45(3), 715-718.
  • Yüksek, H., Üçüncü, O., Alkan, M., Ocak, Z., & Bahceci, S. (2005). Synthesis and non-aqueous medium titrations of some new 4-benzylidenamino-4, 5-dihydro-1H-1, 2, 4-triazol-5-one derivatives. Molecules, 10(8), 961-970.

Year 2021, Volume: 15 , 79 - 87, 31.12.2021

Murat Beytur Haydar Yuksek

https://doi.org/10.55549/epstem.1055607

Abstract

References

  • Aktaş-Yokuş, Ö., Yüksek, H., Manap, S., Aytemiz, F., Alkan, M., Beytur, M., & Gürsoy-Kol, Ö. (2017). In-vitro biological activity of some new 1, 2, 4-triazole derivatives with their potentiometric titrations. Bulgarian Chemical Communications, 49(1), 98-106.
  • Alkan, M., Yüksek, H., İslamoğlu, F., Bahçeci, S., Calapoğlu, M., Elmastaş, M., ... & Özdemir, M. (2007). A Study on 4-Acylamino-4, 5-dihydro-1H-1, 2, 4-triazol-5-ones. Molecules, 12(8), 1805-1816.
  • Avcı, D., & Atalay, Y. (2009). Theoretical analysis of vibrational spectra and scaling‐factor of 2‐aryl‐1, 3, 4‐oxadiazole derivatives. International Journal of Quantum Chemistry, 109(2), 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.
  • Bahçeci, Ş. Yıldırım, N. Alkan, M. Gürsoy-Kol Ö., Manap, S., Beytur, M. & Yüksek, H. (2017). Investigation of Antioxidant, Biological and Acidic Properties of New 3-Alkyl(Aryl)-4-(3-acetoxy-4-methoxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones, The Pharmaceutical and Chemical Journal, 4(4), 91-101.
  • Bahçeci, Ş., Yıldırım, N., Gürsoy-Kol, Ö., Manap, S., Beytur, M., & Yüksek, H. (2016). Synthesis, characterization and antioxidant properties of new 3-alkyl (aryl)-4-(3-hydroxy-4-methoxybenzylidenamino)-4, 5-dihydro-1H-1, 2, 4-triazol-5-ones. Rasayan Journal of Chemistry, 9(3), 494-501.
  • Bayrak, H., Demirbas, A., Demirbas, N., & Karaoglu, S. A. (2010). Cyclization of some carbothioamide derivatives containing antipyrine and triazole moieties and investigation of their antimicrobial Beytur, M. (2020).
  • Fabrication of platinum nanoparticle/boron nitride quantum dots/6-methyl-2-(3-hydroxy-4-methoxybenzylidenamino)-benzothiazole (ils) nanocomposite for electrocatalytic oxidation of methanol. Journal of the Chilean Chemical Society, 65(3), 4929-4933.
  • Beytur, M., & Avinca, I. (2021). Molecular, Electronic, Nonlinear Optical and Spectroscopic Analysis of Heterocyclic 3-Substituted-4-(3-methyl-2-thienylmethyleneamino)-4, 5-dihydro-1H-1, 2, 4-triazol-5-ones: Experiment and DFT Calculations. Heterocyclic Communications, 27(1), 1-16.
  • Beytur, M., Irak, Z. T., Manap, S., & 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.
  • Boy, S. Türkan, F. Beytur, M. Aras, A. Akyıldırım O., Sedef Karaman, H., & Yüksek, H. (2021). Synthesis, design, and assessment of novel morpholine-derived Mannich bases as multifunctional agents for the potential enzyme inhibitory properties including docking study, Bioorganic Chemistry. 107, 104524.
  • 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. Shawnee Mission.
  • Fukui, K. (1982). Role of frontier orbitals in chemical reactions. science, 218(4574), 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.
  • Güzeldemirci 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.
  • Koç, E., Yüksek, H., Beytur, M., Akyıldırım, O., Akçay, M., & Beytur, C. (2020). Heterosiklik 4, 5-dihidro-1H-1, 2, 4-triazol-5-on türevinin antioksidan özelliğinin erkek ratlarda (wistar albino) in vivo olarak belirlenmesi. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, 9(2), 542-548.
  • 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. The Journal of Chemical Physics, 23(10), 1833-1840.
  • Rani, A. U., Sundaraganesan, N., Kurt, M., Cinar, M., & Karabacak, M. (2010). FT-IR, FT-Raman, NMR spectra and DFT calculations on 4-chloro-N-methylaniline. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 75(5), 1523-1529.
  • Silverstein, R. M., & Bassler, G. C. (1962). Spectrometric identification of organic compounds. Journal of Chemical Education, 39(11), 546.
  • 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. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 76(2), 259-269.
  • 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 incelenmesi. 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.
  • Uğurlu, G., & Beytur, M. (2020). Theoretical studies on the structural, vibrational, conformational analysis and nonlinear optic (NLO) property of 4-(Methoxycarbonyl) phenylboronic acid. Indian Journal of Chemistry-Section A, 59(10), 1504-1512.
  • Vasavada, J. A., & Parekh, H. H. (2003). Synthesis and antimicrobial screening of cyclohexenones and oxazines. ChemInform, 34(39), 55-56.
  • Wade, L.G. (2006). Organic chemistry (6nd ed). Pearson Prentice Hall.
  • 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, 45(3), 715-718.
  • Yüksek, H., Üçüncü, O., Alkan, M., Ocak, Z., & Bahceci, S. (2005). Synthesis and non-aqueous medium titrations of some new 4-benzylidenamino-4, 5-dihydro-1H-1, 2, 4-triazol-5-one derivatives. Molecules, 10(8), 961-970.
There are 31 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Murat Beytur

Haydar Yuksek

Early Pub Date January 1, 2022
Publication Date December 31, 2021
Published in Issue Year 2021 Volume: 15

Cite

APA Beytur, M., & Yuksek, H. (2021). The Investigation of Spectroscopic and Electronic Properties of 3-Ethyl-4-(4-cinnamoyloxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one Compound Using Density Functional Theory and Hartree-Fock Basis Sets. The Eurasia Proceedings of Science Technology Engineering and Mathematics, 15, 79-87. https://doi.org/10.55549/epstem.1055607
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