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Theoretical (6-311G(d,p)/ 3-21G) and Spectroscopic (13C/ 1H-NMR, FT-IR) Analyses pf 3-Propyl-4-[3-(2-Methylbenzoxy)-Benzylidenamino]-4,5-Dihydro-1h-1,2,4-Triazol-5-One Molecule

Year 2021, Volume: 15 , 42 - 53, 31.12.2021

Songul Ulufer-bulut Gul Kotan Haydar Yuksek

https://doi.org/10.55549/epstem.1055594

Abstract

The molecule was studied with the method Density Functional Theory (DFT) using two different the basis sets (6-311G(d,p)/ 3-21G) in the Gaussian 09W program. First, the most stable three-dimensional shape of the molecule was determined with the GaussView5.0 program (Dennington et al., 2009). Based on the structure of this optimized molecule,"spectroscopic properties"(FT-IR, 13C/ 1H-NMR), the electronic properties (electron affinity (A), ionization potential (I), electronegativity (χ), chemical hardness and softness, electrophilic and nucleophilic index), HOMO-LUMO energies and ΔEg energy, the geometric properties (bond length and angle) ve the thermodynamic properties (thermal energy (E), thermal capacity (CV), entropy (S)) were calculated with DFT/ 6-311G(d,p) and 3-21G. In addition, the total energy of the molecule, mulliken atomic charge values, dipole moment, molecular electron potential (MEP), total density and contour surface maps were determined. The electrophilic and nucleophilic regions of the structure were confirmed. Theoretical calculations of 13C/ 1H-NMR isotropic shift values were performed in gas phase and solvent (DMSO) acording to GIAO method and regression analyzes were by compare with experimental values of computational data. R2 values were calculated and regression graphs were created. FT-IR (Infrared) vibration frequency values were calculated from the Veda4f program. The theoretical vibration frequency values were compared with the experimental IR values. Experimental data obtained from the literature.

Keywords

1 2 4-Triazole-5-one Giao Mep Homo-Lumo.

References

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  • 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.
  • Becke, A.D. (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Review A: General physics, 38(6), 3098-3100.
  • 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.
  • Fukui, K. (1982). Role of frontier orbitals in chemical reactions. science, 218(4574), 747-754. 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.
  • Gürsoy-Kol, Ö., Yüksek, H., Manap, S., Tokalı, F.S., (2016). Synthesis, Characterization, and antioxidant activities of novel 1-(Morpholine-4-yl-methyl)-3-alkyl(aryl)-4-[4-(dimethylamino)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones. Journal of the Turkish Chemical Society Section A: Chemistry, 3(3), 105-120.
  • 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. Europen. Journal of Medicinal Chemistry, 42(7), 934-939.
  • 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, 57(1): 25-33
  • Jamróz, M. H. (2004). Vibrational energy distribution analysis: VEDA 4 program
  • Klimeová, V., Zahajská, L., Waisser, K., Kaustová, J., Möllmann, U., (2004). Synthesis and antimycobacterial activity of 1,2,4-triazole 3-benzylsulfanyl derivatives. Il Farmaco, 59(4), 279-288
  • Kohn, W., Becke, A. D., & Parr, R. G. (1996). Density functional theory of electronic structure. The Journal of Physical Chemistry, 100(31), 12974-12980.
  • Kotan, G., & Yüksek, H. (2016). Theoretical and Spectroscopic Studies of (E)-3-Benzyl-4-((4-Isopropylbenzylidene)-Amino)-1-(Morpholinomethyl)-1H-1.2.4-triazol-5(4H)-one molecule. Journal of the Turkish Chemical Society Section A: Chemistry, 3(3), 381-392.
  • Küçükgüzel, Ş. 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. European journal of medicinal chemistry, 35(7), 761-771.
  • 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. The Journal of Chemical Physics, 23(10), 1833-1840.
  • 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.
  • 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.
  • Turan-Zitouni, G., Kaplancıklı, Z. A., Yıldız, M. T., Chevallet, P., & Kaya, D. (2005). Synthesis and antimicrobial activity of 4-phenyl/cyclohexyl-5-(1-phenoxyethyl)-3-[N-(2-thiazolyl) acetamido] thio-4H-1, 2, 4-triazole derivatives. European Journal of Medicinal Chemistry, 40(6), 607-613.
  • Ulufer, S., Gürsoy Kol, Ö., Yüksek, H., Bazı yeni 4-[3-(2-metilbenzoksi)-benzilidenamino]-4,5-dihidro-1H-1,2,4-triazol-5-on bileşiklerinin sentezi ve antioksidan özelliklerinin incelenmesi (Bildiri Özeti), 2. Ulusal Organik Kimya Kongresi, Ankara.
  • 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., Gürsoy, O., Cakmak, I., & Alkan, M. (2005). Synthesis and GIAO NMR calculations 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.
  • Chohan, Z. H., Sumrra, S. H., Youssoufi, M. H., & Hadda, T. B. (2010). Metal based biologically active compounds: Design, synthesis, and antibacterial/antifungal/cytotoxic properties of triazole-derived Schiff bases and their oxovanadium (IV) complexes. European Journal of Medicinal Chemistry, 45(7), 2739-2747.

Year 2021, Volume: 15 , 42 - 53, 31.12.2021

Songul Ulufer-bulut Gul Kotan Haydar Yuksek

https://doi.org/10.55549/epstem.1055594

Abstract

References

  • 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.
  • 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.
  • Becke, A.D. (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Review A: General physics, 38(6), 3098-3100.
  • 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.
  • Fukui, K. (1982). Role of frontier orbitals in chemical reactions. science, 218(4574), 747-754. 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.
  • Gürsoy-Kol, Ö., Yüksek, H., Manap, S., Tokalı, F.S., (2016). Synthesis, Characterization, and antioxidant activities of novel 1-(Morpholine-4-yl-methyl)-3-alkyl(aryl)-4-[4-(dimethylamino)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones. Journal of the Turkish Chemical Society Section A: Chemistry, 3(3), 105-120.
  • 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. Europen. Journal of Medicinal Chemistry, 42(7), 934-939.
  • 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, 57(1): 25-33
  • Jamróz, M. H. (2004). Vibrational energy distribution analysis: VEDA 4 program
  • Klimeová, V., Zahajská, L., Waisser, K., Kaustová, J., Möllmann, U., (2004). Synthesis and antimycobacterial activity of 1,2,4-triazole 3-benzylsulfanyl derivatives. Il Farmaco, 59(4), 279-288
  • Kohn, W., Becke, A. D., & Parr, R. G. (1996). Density functional theory of electronic structure. The Journal of Physical Chemistry, 100(31), 12974-12980.
  • Kotan, G., & Yüksek, H. (2016). Theoretical and Spectroscopic Studies of (E)-3-Benzyl-4-((4-Isopropylbenzylidene)-Amino)-1-(Morpholinomethyl)-1H-1.2.4-triazol-5(4H)-one molecule. Journal of the Turkish Chemical Society Section A: Chemistry, 3(3), 381-392.
  • Küçükgüzel, Ş. 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. European journal of medicinal chemistry, 35(7), 761-771.
  • 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. The Journal of Chemical Physics, 23(10), 1833-1840.
  • 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.
  • 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.
  • Turan-Zitouni, G., Kaplancıklı, Z. A., Yıldız, M. T., Chevallet, P., & Kaya, D. (2005). Synthesis and antimicrobial activity of 4-phenyl/cyclohexyl-5-(1-phenoxyethyl)-3-[N-(2-thiazolyl) acetamido] thio-4H-1, 2, 4-triazole derivatives. European Journal of Medicinal Chemistry, 40(6), 607-613.
  • Ulufer, S., Gürsoy Kol, Ö., Yüksek, H., Bazı yeni 4-[3-(2-metilbenzoksi)-benzilidenamino]-4,5-dihidro-1H-1,2,4-triazol-5-on bileşiklerinin sentezi ve antioksidan özelliklerinin incelenmesi (Bildiri Özeti), 2. Ulusal Organik Kimya Kongresi, Ankara.
  • 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., Gürsoy, O., Cakmak, I., & Alkan, M. (2005). Synthesis and GIAO NMR calculations 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.
  • Chohan, Z. H., Sumrra, S. H., Youssoufi, M. H., & Hadda, T. B. (2010). Metal based biologically active compounds: Design, synthesis, and antibacterial/antifungal/cytotoxic properties of triazole-derived Schiff bases and their oxovanadium (IV) complexes. European Journal of Medicinal Chemistry, 45(7), 2739-2747.
There are 22 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Songul Ulufer-bulut

Gul Kotan

Haydar Yuksek

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

Cite

APA Ulufer-bulut, S., Kotan, G., & Yuksek, H. (2021). Theoretical (6-311G(d,p)/ 3-21G) and Spectroscopic (13C/ 1H-NMR, FT-IR) Analyses pf 3-Propyl-4-[3-(2-Methylbenzoxy)-Benzylidenamino]-4,5-Dihydro-1h-1,2,4-Triazol-5-One Molecule. The Eurasia Proceedings of Science Technology Engineering and Mathematics, 15, 42-53. https://doi.org/10.55549/epstem.1055594
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