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Experimental (FT-IR, 13C/1H-NMR) and DFT (B3LYP, B3PW91) Studies of 3-n-Propyl-4-[2-(4-Methoxybenzoxy)-3-Methoxy] Benzylidenamino-4,5-Dihydro-1h-1,2,4-Triazol-5-Ones Molecule

Year 2021, Volume: 15 , 69 - 78, 31.12.2021

Gul Kotan Muzaffer Alkan Haydar Yuksek

https://doi.org/10.55549/epstem.1055604

Abstract

All theoretical calculations of 3-n-propyl-4-[2-(4-methoxybenzoxy)-3-methoxy] benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones has been performed with B3LYP/B3PW91 functions of DFT method using the 6-311G(d,p) basis set (Frisch et al., 2009; Wolinski et. al., 1990). Firstly, optimized to achieve the most stable form of the molecule. Then, the veda4f program was used in defining Infrared (IR) data (Jamróz, 2004). The standard error values were found via the Sigma plot with regression coefficient of a and b constants. The vibrational frequency values of this molecule have been calculated by using 6-311G(d,p) basis set with DFT (B3LYP/ B3PW91) methods. Then, these values are scaled with appropriate scala factors (Merrick et al., 2007). 1H-NMR and 13C-NMR spectral values according to GIAO method (Wolinski et al., 1990) was calculated using Gaussian G09W program package in DMSO solvent and in gas phase. Theoretical spectral values of molecule were compared with experimental values. Experimental data obtained from the literature (Alkan et al., 2014). In addition, electronic properties (electronegativity (χ), global hardness (η), electron affinity (A), ionization potential (I), softness (σ), thermodynamics properties (heat capacity CV0, entropy S0 and enthalpy H0), HOMO-LUMO energy, ELUMO-EHOMO energy gap (ΔEg), geometric properties (bond angles, bond lengths), dipole moments, Mulliken atomic charges, total energy of the molecule were calculated. Finally, the molecular surfaces such as the electron density, molecular electrostatic potential (MEP), contour and the total density maps were designated.

Keywords

B3LYP B3PW91 DFT HOMO-LUMO MEP.

References

  • Alkan, M., Gürbüz, A., Yüksek, H., Kol, Ö. G., & Zafer, O. (2014). Synthesis and non-aqueus medium titrations of some new 3-alkyl(aryl)-4-[2-(4-methoxybenzoxy)-3-methoxy]-benzylidenamino-4,5-dihydro-1H-1, 2, 4-trıazol-5-ones. Caucasian Journal Of Science, 1(1), 138-148.
  • Amim, R. S., Pessoa, C., CS Lourenco, M., VN de Souza, M., & A Lessa, J. (2017). Synthesis, Antitubercular and Anticancer Activities of p-nitrophenylethylenediamine-derived Schiff Bases. Medicinal Chemistry, 13(4), 391-397.
  • 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.
  • Demirbaş, N., Ug̵urluog̵lu, R., & Demirbaş, A. (2002). Synthesis of 3-alkyl (Aryl)-4-alkylidenamino-4, 5-dihydro-1H-1, 2, 4-triazol-5-ones and 3-alkyl-4-alkylamino-4, 5-dihydro-1H-1, 2, 4-triazol-5-ones as antitumor agents. Bioorganic & Medicinal Chemistry, 10(12), 3717-3723.
  • Dharmaraj, N., Viswanathamurthi, P., & Natarajan, K. (2001). Ruthenium (II) complexes containing bidentate Schiff bases and their antifungal activity. Transition Metal Chemistry, 26(1), 105-109.
  • Fukui, K. (1982). Role of frontier orbitals in chemical reactions. Science, 218(4574), 747-754.
  • Jamróz, M. H. (2004). Vibrational energy distribution analysis. VEDA 4 Program.
  • Kotan, G., & Yüksek, H. (2021). 2-(3-Fenil-4, 5-dihidro-1H-1, 2, 4-triazol-5-on-4-il)-azometin benzoik asid Molekülünün Deneysel ve Kuantum Kimyasal Hesaplamaları. Avrupa Bilim ve Teknoloji Dergisi, (21), 649-659.
  • Kotan, G., (2021). novel mannich base derivatives: synthesis, characterization, antimicrobial and antioxidant activities. Letters in Organic Chemistry, 18(10), 830-841.
  • Kotan, G., Gökce, H., Akyıldırım, O., Yüksek, H., Beytur, M., Manap, S., & Medetalibeyoğlu, H. (2020). Synthesis, Spectroscopic and Computational Analysis of 2-[(2-Sulfanyl-1 H-benzo [d] imidazol-5-yl) iminomethyl] phenyl Naphthalene-2-sulfonate. Russian Journal of Organic Chemistry, 56(11), 1982-1994.
  • Manap, S., Gürsoy-Kol, Ö., Alkan, M., & Yüksek, H. (2020). Synthesis, in vitro antioxidant and antimicrobial activities of some novel 3-substitued-4-(3-methoxy-4-isobutyryloxybenzylideneamino)-4, 5-dihydro-1H-1, 2, 4-triazol-5-one derivatives. Indian Journal of Chemistry, 59(2), 271-282.
  • Merrick, J. P., Moran, D., Radom, L. (2007). An evaluation of harmonic vibrational frequency scale factors. Journal of Physical Chemistry, 111(45), 11683-11700.
  • Mulliken, R. S. (1955). Electronic population analysis on LCAO–MO molecular wave functions. I. The Journal of Chemical Physics, 23(10), 1833-1840.
  • Rana, K., Pandurangan, A., Singh, N., & Tiwari, A. (2012). A systemic review of schiff bases as an analgesic, anti-inflammatory. International Journal of Current. Pharmaceutical Research, 4(2), 5-11.
  • Shukla, P. K., Soni, N., Verma, A., & Jha, A. K. (2014). Synthesis, characterization and in vitro biological evaluation of a series of 1, 2, 4-triazoles derivatives & triazole based schiff bases. Der Pharma Chemica, 6(3), 153-160.
  • Sudha, N., Abinaya, B., Arun Kumar, R., & Mathammal, R. (2018). Synthesis, structural, spectral, optical and mechanical study of benzimidazolium phthalate crystals for NLO applications. Journal of Lasers Optics & Photonics, 5(2), 1-6.
  • Uddin, N., Rashid, F., Ali, S., Tirmizi, S. A., Ahmad, I., Zaib, S., ... & Haider, A. (2020). Synthesis, characterization, and anticancer activity of Schiff bases. Journal of Biomolecular Structure and Dynamics, 38(11), 3246-3259.
  • 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., Gursoy-Kol, O., Kemer, G., Ocak, Z., & Anil, B. (2011). Synthesis and in-vitro antioxidant evaluation of some novel 4-(4-substituted) benzylidenamino-4, 5-dihydro-1H-1, 2, 4-triazol-5-ones.
  • Yüksek, H., Kotan, G., Medetalibeyoğlu, H., Gürbüz, A., & Alkan, M. (2017). B3LYP ve HF Temel Setleri Kullanılarak Bazı 3-Alkil-4-(2-asetoksi-3-metoksibenzilidenamino)-4, 5-dihidro-1H-1, 2, 4-triazol-5-on Bileşiklerinin Deneysel ve Teorik Özelliklerinin İncelenmesi/The Investigation of Experimental and Theoretical Properties of Some 3-Alkyl-4-(2-acetoxy-3-methoxybenzylidenamino)-4, 5-dihydro-1H-1, 2, 4-triazol-5-one Using B3LYP and HF Basis Sets. Celal Bayar University Journal of Science, 13(1), 193-204.

Year 2021, Volume: 15 , 69 - 78, 31.12.2021

Gul Kotan Muzaffer Alkan Haydar Yuksek

https://doi.org/10.55549/epstem.1055604

Abstract

References

  • Alkan, M., Gürbüz, A., Yüksek, H., Kol, Ö. G., & Zafer, O. (2014). Synthesis and non-aqueus medium titrations of some new 3-alkyl(aryl)-4-[2-(4-methoxybenzoxy)-3-methoxy]-benzylidenamino-4,5-dihydro-1H-1, 2, 4-trıazol-5-ones. Caucasian Journal Of Science, 1(1), 138-148.
  • Amim, R. S., Pessoa, C., CS Lourenco, M., VN de Souza, M., & A Lessa, J. (2017). Synthesis, Antitubercular and Anticancer Activities of p-nitrophenylethylenediamine-derived Schiff Bases. Medicinal Chemistry, 13(4), 391-397.
  • 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.
  • Demirbaş, N., Ug̵urluog̵lu, R., & Demirbaş, A. (2002). Synthesis of 3-alkyl (Aryl)-4-alkylidenamino-4, 5-dihydro-1H-1, 2, 4-triazol-5-ones and 3-alkyl-4-alkylamino-4, 5-dihydro-1H-1, 2, 4-triazol-5-ones as antitumor agents. Bioorganic & Medicinal Chemistry, 10(12), 3717-3723.
  • Dharmaraj, N., Viswanathamurthi, P., & Natarajan, K. (2001). Ruthenium (II) complexes containing bidentate Schiff bases and their antifungal activity. Transition Metal Chemistry, 26(1), 105-109.
  • Fukui, K. (1982). Role of frontier orbitals in chemical reactions. Science, 218(4574), 747-754.
  • Jamróz, M. H. (2004). Vibrational energy distribution analysis. VEDA 4 Program.
  • Kotan, G., & Yüksek, H. (2021). 2-(3-Fenil-4, 5-dihidro-1H-1, 2, 4-triazol-5-on-4-il)-azometin benzoik asid Molekülünün Deneysel ve Kuantum Kimyasal Hesaplamaları. Avrupa Bilim ve Teknoloji Dergisi, (21), 649-659.
  • Kotan, G., (2021). novel mannich base derivatives: synthesis, characterization, antimicrobial and antioxidant activities. Letters in Organic Chemistry, 18(10), 830-841.
  • Kotan, G., Gökce, H., Akyıldırım, O., Yüksek, H., Beytur, M., Manap, S., & Medetalibeyoğlu, H. (2020). Synthesis, Spectroscopic and Computational Analysis of 2-[(2-Sulfanyl-1 H-benzo [d] imidazol-5-yl) iminomethyl] phenyl Naphthalene-2-sulfonate. Russian Journal of Organic Chemistry, 56(11), 1982-1994.
  • Manap, S., Gürsoy-Kol, Ö., Alkan, M., & Yüksek, H. (2020). Synthesis, in vitro antioxidant and antimicrobial activities of some novel 3-substitued-4-(3-methoxy-4-isobutyryloxybenzylideneamino)-4, 5-dihydro-1H-1, 2, 4-triazol-5-one derivatives. Indian Journal of Chemistry, 59(2), 271-282.
  • Merrick, J. P., Moran, D., Radom, L. (2007). An evaluation of harmonic vibrational frequency scale factors. Journal of Physical Chemistry, 111(45), 11683-11700.
  • Mulliken, R. S. (1955). Electronic population analysis on LCAO–MO molecular wave functions. I. The Journal of Chemical Physics, 23(10), 1833-1840.
  • Rana, K., Pandurangan, A., Singh, N., & Tiwari, A. (2012). A systemic review of schiff bases as an analgesic, anti-inflammatory. International Journal of Current. Pharmaceutical Research, 4(2), 5-11.
  • Shukla, P. K., Soni, N., Verma, A., & Jha, A. K. (2014). Synthesis, characterization and in vitro biological evaluation of a series of 1, 2, 4-triazoles derivatives & triazole based schiff bases. Der Pharma Chemica, 6(3), 153-160.
  • Sudha, N., Abinaya, B., Arun Kumar, R., & Mathammal, R. (2018). Synthesis, structural, spectral, optical and mechanical study of benzimidazolium phthalate crystals for NLO applications. Journal of Lasers Optics & Photonics, 5(2), 1-6.
  • Uddin, N., Rashid, F., Ali, S., Tirmizi, S. A., Ahmad, I., Zaib, S., ... & Haider, A. (2020). Synthesis, characterization, and anticancer activity of Schiff bases. Journal of Biomolecular Structure and Dynamics, 38(11), 3246-3259.
  • 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., Gursoy-Kol, O., Kemer, G., Ocak, Z., & Anil, B. (2011). Synthesis and in-vitro antioxidant evaluation of some novel 4-(4-substituted) benzylidenamino-4, 5-dihydro-1H-1, 2, 4-triazol-5-ones.
  • Yüksek, H., Kotan, G., Medetalibeyoğlu, H., Gürbüz, A., & Alkan, M. (2017). B3LYP ve HF Temel Setleri Kullanılarak Bazı 3-Alkil-4-(2-asetoksi-3-metoksibenzilidenamino)-4, 5-dihidro-1H-1, 2, 4-triazol-5-on Bileşiklerinin Deneysel ve Teorik Özelliklerinin İncelenmesi/The Investigation of Experimental and Theoretical Properties of Some 3-Alkyl-4-(2-acetoxy-3-methoxybenzylidenamino)-4, 5-dihydro-1H-1, 2, 4-triazol-5-one Using B3LYP and HF Basis Sets. Celal Bayar University Journal of Science, 13(1), 193-204.
There are 20 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Gul Kotan

Muzaffer Alkan

Haydar Yuksek

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

Cite

APA Kotan, G., Alkan, M., & Yuksek, H. (2021). Experimental (FT-IR, 13C/1H-NMR) and DFT (B3LYP, B3PW91) Studies of 3-n-Propyl-4-[2-(4-Methoxybenzoxy)-3-Methoxy] Benzylidenamino-4,5-Dihydro-1h-1,2,4-Triazol-5-Ones Molecule. The Eurasia Proceedings of Science Technology Engineering and Mathematics, 15, 69-78. https://doi.org/10.55549/epstem.1055604
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