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In Silico Calculations of 2-Methoxy-6-[(3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)-iminomethyl] Phenyl Benzoate

Year 2021, Volume: 15 , 54 - 62, 31.12.2021

Murat Beytur Haydar Yuksek

https://doi.org/10.55549/epstem.1055598

Abstract

Schiff's bases are significant compound for organic chemistry. In the last year, computational properties of Schiff bases were examined on a computer. In this study, we investigated theoretical features of 2-methoxy-6-[(3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)-iminomethyl] phenyl benzoate with B3LYP/6-311G(d) basis set. All quantum chemical calculations were carried out using the Gaussian09W program package and the Gauss View molecular visualization program. The IR vibrational frequency values of the titled compound were calculated using B3LYP/6-311G(d) basis set. The vibrational spectral analysis was carried out using infrared spectroscopy in the range 4000-400 cm-1 for titled compound. The IR vibrational frequency values were defined using the veda4f software. The 1H-NMR and 13C-NMR spectral values of the titled compound were calculated utilizing the B3LYP/6-311G(d) basis set. To determine the 1H-NMR and 13C-NMR isotropic shift values, the gauge independent atomic orbital (GIAO) methodology was used. The UV-vis spectral calculations in the ethanol solvent of the titled compound were performed via the same basis set. TD-DFT computations in ethanol solvent were used to identify the UV-Vis spectral analyses. In addition, dipole moments, LUMO-HOMO, total energy, and electronic properties; ELUMO-EHOMO energy gap (ΔEg), electronegativity (χ), electron affinity (A), global hardness (η), softness (σ), ionization potential (I), thermodynamics properties; (thermal energies (E), thermal capacity (CV), entropy (S) were calculated.

Keywords

Schiff base Gaussian09W GIAO UV-vis HOMO-LUMO

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., 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 (Vol. 22). Royal Society of Chemistry.
  • 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.
  • Aytac, S. P., Tozkoparan, B., Kaynak, F. B., Aktay, G., Goktas, O., & Unuvar, S. (2009). Synthesis of 3,6-disubstituted 7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines as novel analgesic/anti-inflammatory compounds, European Journal of Medicinal Chemistry, 44(11), 4528-4538.
  • 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.
  • Becke, A. D. (1993). Density functional thermochemistry. III. The role of exact Exchange, The Journal of Chemical Physics, 98, 5648-5652.
  • 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. (2017). 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.
  • Frisch, A., Nielson, A. B., & Holder, A. J. (2003). Gaussvıew User Manual. Inc. Wallingford.
  • Gürbüz, A., Alkan, M., Manap, S., Özdemir, G.,Yüksek, H. (2021). Synthesis and antimicrobial activities of novel 2-methoxy-6-[(3-alkyl-4,5-dihydro-1h-1,2,4-triazol-5-one-4- yl)-azomethin]-phenyl benzoates with their nonaqueous medium titrations. World Journal of Pharmacy and Pharmaceutical Sciences. 10(9), 65-80
  • Gürsoy-Kol, O., & Yuksek, H. (2010). Synthesis and in vitro antioxidant evaluation of some novel 4, 5-dihydro-1H, 2, 4-triazol-5-one derivatives. E-Journal of Chemistry, 7(1), 123-136.
  • Jamróz, M. H. (2004). Vibrational Energy Distribution Analysis: VEDA 4 program.
  • 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. Bulletin of the Korean Chemical Society, 19(1), 93-98.
  • 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.
  • Turhan-Irak Z., & Gümüş, S. (2017). Heterotricyclic compounds via click reaction: A computational study. Noble International Journal of Scientific Research, 1(7), 80-89.
  • 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.
  • 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(8), 1200-1211.
  • Wade, Jr. L.G. (2006). Organic Chemistry (6nd ed.). Pearson Prentice Hall.
  • Wolinski, K., Hinton, 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(23), 8251-8260.
  • 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).
  • Yüksek, H., Bahceci, S., Ocak, Z., Alkan, M., Ermis, B., Mutlu, T., Ocak, M., & Ozdemir, M. (2004). Synthesis of some 4,5-dihydro-1H-1,2,4-triazol-5-ones, Indian journal of heterocyclic chemistry, 13(4), 369-372.
  • Yüksek, H., Kucuk, M., ALKAN, M., BAHCECI, Ş., Kolayli, S., Ocak, Z., ... & Ocak, M. (2006). Synthesis and antioxidant activities of some new 4-(4-hydroxybenzylidenamino)-4, 5-dihydro-1H-1, 2, 4-triazol-5-one derivatives with their acidic properties. Asian Journal of Chemistry, 18(1).
  • 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 , 54 - 62, 31.12.2021

Murat Beytur Haydar Yuksek

https://doi.org/10.55549/epstem.1055598

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., 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 (Vol. 22). Royal Society of Chemistry.
  • 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.
  • Aytac, S. P., Tozkoparan, B., Kaynak, F. B., Aktay, G., Goktas, O., & Unuvar, S. (2009). Synthesis of 3,6-disubstituted 7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines as novel analgesic/anti-inflammatory compounds, European Journal of Medicinal Chemistry, 44(11), 4528-4538.
  • 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.
  • Becke, A. D. (1993). Density functional thermochemistry. III. The role of exact Exchange, The Journal of Chemical Physics, 98, 5648-5652.
  • 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. (2017). 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.
  • Frisch, A., Nielson, A. B., & Holder, A. J. (2003). Gaussvıew User Manual. Inc. Wallingford.
  • Gürbüz, A., Alkan, M., Manap, S., Özdemir, G.,Yüksek, H. (2021). Synthesis and antimicrobial activities of novel 2-methoxy-6-[(3-alkyl-4,5-dihydro-1h-1,2,4-triazol-5-one-4- yl)-azomethin]-phenyl benzoates with their nonaqueous medium titrations. World Journal of Pharmacy and Pharmaceutical Sciences. 10(9), 65-80
  • Gürsoy-Kol, O., & Yuksek, H. (2010). Synthesis and in vitro antioxidant evaluation of some novel 4, 5-dihydro-1H, 2, 4-triazol-5-one derivatives. E-Journal of Chemistry, 7(1), 123-136.
  • Jamróz, M. H. (2004). Vibrational Energy Distribution Analysis: VEDA 4 program.
  • 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. Bulletin of the Korean Chemical Society, 19(1), 93-98.
  • 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.
  • Turhan-Irak Z., & Gümüş, S. (2017). Heterotricyclic compounds via click reaction: A computational study. Noble International Journal of Scientific Research, 1(7), 80-89.
  • 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.
  • 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(8), 1200-1211.
  • Wade, Jr. L.G. (2006). Organic Chemistry (6nd ed.). Pearson Prentice Hall.
  • Wolinski, K., Hinton, 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(23), 8251-8260.
  • 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).
  • Yüksek, H., Bahceci, S., Ocak, Z., Alkan, M., Ermis, B., Mutlu, T., Ocak, M., & Ozdemir, M. (2004). Synthesis of some 4,5-dihydro-1H-1,2,4-triazol-5-ones, Indian journal of heterocyclic chemistry, 13(4), 369-372.
  • Yüksek, H., Kucuk, M., ALKAN, M., BAHCECI, Ş., Kolayli, S., Ocak, Z., ... & Ocak, M. (2006). Synthesis and antioxidant activities of some new 4-(4-hydroxybenzylidenamino)-4, 5-dihydro-1H-1, 2, 4-triazol-5-one derivatives with their acidic properties. Asian Journal of Chemistry, 18(1).
  • 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 34 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 2021Volume: 15

Cite

APA Beytur, M., & Yuksek, H. (2021). In Silico Calculations of 2-Methoxy-6-[(3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)-iminomethyl] Phenyl Benzoate. The Eurasia Proceedings of Science Technology Engineering and Mathematics, 15, 54-62. https://doi.org/10.55549/epstem.1055598
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