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Investigation of Theoretical and Experimentical Properties of 2-[3-(n-Propyl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-Phenoxyacetic Acide

Year 2021, Volume: 15 , 1 - 9, 31.12.2021

Murat Beytur Haydar Yuksek

https://doi.org/10.55549/epstem.1052141

Abstract

In the present study, 2-[3-(n-propyl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-phenoxyacetic acide was optimized by using B3LYP/6-311+G(d,p) basis set. Firstly, IR data of the compound were calculated in gas phase by using of 6-311+G(d,p) 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. Then, 1H-NMR and 13C-NMR spectral data values were calculated according to the method of GIAO using the program package Gaussian G09W Software. Experimental data were obtained from the literature. 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. Furthermore, molecular structure, HOMO and LUMO energy analysis, electronic transitions, total static dipol moment (μ), the mean polarizability (<α>), the anisotropy of the polarizability (Δα), the mean first-order hyperpolarizability (<β>), electronegativity (), hardness (), molecular electrostatic potential maps (MEP), and Mulliken charges of 2-[3-(n-propyl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-phenoxyacetic acide have been investigated by using B3LYP level with the 6-311+G(d,p) basis set.

Keywords

Phenoxyacetic acide Hyperpolarizability Theoretical.

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.
  • Azam, F., Singh, S., Khokhra, S. L., & Prakash, O. (2007). Synthesis of Schiff bases of naphtha [1, 2-d] thiazol-2-amine and metal complexes of 2-(2′-hydroxy) benzylideneaminonaphthothiazole as potential antimicrobial agents. Journal of Zhejiang University Science B, 8(6), 446-452.
  • 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. (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.
  • Frisch, A., Nielson, A.B., & Holder, A.J. (2003). Gaussvıew User Manual. In Gaussian, Inc., Wallingford.
  • Govindarajan, M., Periandy, S., & Carthigayen, K. (2012). FT-IR and FT-Raman spectra, thermo dynamical behavior, HOMO and LUMO, UV, NLO properties, computed frequency estimation analysis and electronic structure calculations on α-bromotoluene. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 97, 411-422.
  • 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.
  • Jamróz, M. H. (2004). Vibrational Energy Distribution Analysis. VEDA 4 Program.
  • Kido, J., Kimura, M., & Nagai, K. (1995). Multilayer white light-emitting organic electroluminescent device. Science, 267(5202), 1332-1334.
  • 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) İn 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.
  • Mecca, C. Z., Fonseca, F. L., & Bagatin, I. A. (2016). Fluorescence in complexes based on quinolines-derivatives: a search for better fluorescent probes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 168, 104-110.
  • Mulliken, R. S. (1955). Electronic population analysis on LCAO–MO molecular wave functions. I. The Journal of Chemical Physics, 23(10), 1833-1840.
  • Qin, J.C., Yang, Z.Y., Fan, L. & Wang, B.D. (2015). Fluorescent sensor for selective detection of Al(3+) based on quinoline-coumarin conjugate, Spectrochimica Acta Part A, 140, 21-26.
  • 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.
  • 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.
  • Sun, Y., Giebink, N. C., Kanno, H., Ma, B., Thompson, M. E., & Forrest, S. R. (2006). Management of singlet and triplet excitons for efficient white organic light-emitting devices. Nature, 440(7086), 908-912.
  • Sztanke, K., Maziarka, A., Osinka, A. & Sztanke, M. (2003). Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4'-chlorophenyl) thiazol-2-yl] thiosemicarbazide. European Journal of Pharmaceutical Sciences. 21(13), 3648-3666.
  • Turhan-Irak Z., Beytur, M. (2019). 4-Benzilidenamino-4,5-dihidro-1H-1,2,4-triazol-5-on Türevlerinin Antioksidan Aktivitelerinin Teorik Olarak İncelenmesi, 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, 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.
  • Yang, D., Duan, Y., Yang, Y., Hu, N., Wang, X., Sun, F., & Duan, Y. (2015). Application of exciplex in the fabrication of white organic light emitting devices with mixed fluorescent and phosphorescent layers. Journal of Luminescence, 166, 77-81.
  • 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.
  • Zhao, J., Wang, Z., Wang, R., Chi, Z., & Yu, J. (2017). Hybrid white organic light-emitting devices consisting of a non-doped thermally activated delayed fluorescent emitter and an ultrathin phosphorescent emitter. Journal of Luminescence, 184, 287-292.

Year 2021, Volume: 15 , 1 - 9, 31.12.2021

Murat Beytur Haydar Yuksek

https://doi.org/10.55549/epstem.1052141

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.
  • Azam, F., Singh, S., Khokhra, S. L., & Prakash, O. (2007). Synthesis of Schiff bases of naphtha [1, 2-d] thiazol-2-amine and metal complexes of 2-(2′-hydroxy) benzylideneaminonaphthothiazole as potential antimicrobial agents. Journal of Zhejiang University Science B, 8(6), 446-452.
  • 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. (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.
  • Frisch, A., Nielson, A.B., & Holder, A.J. (2003). Gaussvıew User Manual. In Gaussian, Inc., Wallingford.
  • Govindarajan, M., Periandy, S., & Carthigayen, K. (2012). FT-IR and FT-Raman spectra, thermo dynamical behavior, HOMO and LUMO, UV, NLO properties, computed frequency estimation analysis and electronic structure calculations on α-bromotoluene. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 97, 411-422.
  • 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.
  • Jamróz, M. H. (2004). Vibrational Energy Distribution Analysis. VEDA 4 Program.
  • Kido, J., Kimura, M., & Nagai, K. (1995). Multilayer white light-emitting organic electroluminescent device. Science, 267(5202), 1332-1334.
  • 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) İn 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.
  • Mecca, C. Z., Fonseca, F. L., & Bagatin, I. A. (2016). Fluorescence in complexes based on quinolines-derivatives: a search for better fluorescent probes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 168, 104-110.
  • Mulliken, R. S. (1955). Electronic population analysis on LCAO–MO molecular wave functions. I. The Journal of Chemical Physics, 23(10), 1833-1840.
  • Qin, J.C., Yang, Z.Y., Fan, L. & Wang, B.D. (2015). Fluorescent sensor for selective detection of Al(3+) based on quinoline-coumarin conjugate, Spectrochimica Acta Part A, 140, 21-26.
  • 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.
  • 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.
  • Sun, Y., Giebink, N. C., Kanno, H., Ma, B., Thompson, M. E., & Forrest, S. R. (2006). Management of singlet and triplet excitons for efficient white organic light-emitting devices. Nature, 440(7086), 908-912.
  • Sztanke, K., Maziarka, A., Osinka, A. & Sztanke, M. (2003). Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4'-chlorophenyl) thiazol-2-yl] thiosemicarbazide. European Journal of Pharmaceutical Sciences. 21(13), 3648-3666.
  • Turhan-Irak Z., Beytur, M. (2019). 4-Benzilidenamino-4,5-dihidro-1H-1,2,4-triazol-5-on Türevlerinin Antioksidan Aktivitelerinin Teorik Olarak İncelenmesi, 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, 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.
  • Yang, D., Duan, Y., Yang, Y., Hu, N., Wang, X., Sun, F., & Duan, Y. (2015). Application of exciplex in the fabrication of white organic light emitting devices with mixed fluorescent and phosphorescent layers. Journal of Luminescence, 166, 77-81.
  • 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.
  • Zhao, J., Wang, Z., Wang, R., Chi, Z., & Yu, J. (2017). Hybrid white organic light-emitting devices consisting of a non-doped thermally activated delayed fluorescent emitter and an ultrathin phosphorescent emitter. Journal of Luminescence, 184, 287-292.
There are 36 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). Investigation of Theoretical and Experimentical Properties of 2-[3-(n-Propyl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-Phenoxyacetic Acide. The Eurasia Proceedings of Science Technology Engineering and Mathematics, 15, 1-9. https://doi.org/10.55549/epstem.1052141
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