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Year 2019, Volume: 7 , 363 - 370, 24.11.2019

Abstract

References

  • Abramov, Yu. A., Volkov, A. V. & Coppens, P. (1999). On the evaluation of molecular dipole moments from multipole refinement of X-ray diffraction data. Chemical Physics Letters, 311 (1-2), 81-86. Aktaş Yokuş, A. (2012). Bazı Yeni 1,2,4-Triazol Türevlerinin Sentezi ve Biyolojik Aktivitelerinin İncelenmesi. Doktora Tezi, Kafkas Üniversitesi Fen Bilimleri Enstitüsü, Kars. Becke A. D. (1993). Density functional thermochemistry. III. The role of exact Exchange, The Journal of Chemical Physics, 98, 5648-5652. Beytur, M., Turhan Irak, Z., Manap, S., and 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, 1-8. Cheeseman, J. R., Trucks, G. W., Keith, T. A. & Frisch. M. J. (1996). A comparison of models for calculating nuclear magnetic resonance shielding tensors. The Journal of Chemical Physics, 104 (14), 5497. 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. Ditchfield, R. (1974). Self-consistent perturbation theory of diamagnetism. Molecular Physics, 27 (4), 789-807. Frisch, M. J., Trucks, G., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J. A., Jr. Vreven, T., Peralta, J. E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, N., Staroverov, V. N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M., Knox, J. E., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Martin, L. R., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J., Dapprich, S., Daniels, A. D., Farkas, O., Foresman, J. B., Ortiz, J. V., Cioslowski, J. & Fox, D. J. (2009). Gaussian Inc., Wallingford, CT. Friesner, R. A., Murphy, R. B., Beachy, M. D., Ringnalda, M. N., Pollard, W. T., Dunietz, B.D. & Cao, Y. (1999). Correlated ab Initio Electronic Structure Calculations for Large Molecules, The Journal of Physical Chemistry A, 103 (13), 1913-1928. Forsyth, D. A. & Sebag. A. B. (1997). Computed 13C NMR Chemical Shifts via Empirically Scaled GIAO Shieldings and Molecular Mechanics Geometries. Conformation and Configuration from 13C Shifts, Journal of the American Chemical Society, 119 (40), 9483-9494. Gürsoy Kol, Ö., and 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. Handy, N. C., Maslen, P. E., Amons, R. D., Audrows, J. S., Murroy, C. W. & Lawing, G. (1992). The harmonic frequencies of benzene. Chemical Physics Letters, 197 (4-5), 506-515. Holla, B.S., Poojary, K.N., Rao, B.S. & Shivananda, M. K.. (2002). New bis-aminomercaptotriazoles and bis-triazolothiadiazoles as possible anticancer agents. European Journal of Medicinal Chemistry, 37 (6), 511-517. Jamróz, M. H. (2004). Vibrational Energy Distribution Analysis: VEDA 4 program, Warsaw. 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. Li, W., Wu, Q., Ye, Y., Luo, M., Hu, L., Gu, Y. & Niu. F. (2004). Density functional theory and ab initio studies of geometry, electronicstructure and vibrational spectra of novel benzothiazoleand benzotriazole herbicides. Spectrochimica Acta Part A, 60, 2343-2353. Keith, T. A., Bader, R. F. W., (2002). Calculation of magnetic response properties using a continuous set of gauge transformations. Chemical Physics Letters, 210 (1-3), 223-231. Kritsanida, M., Mouroutsou, A., Marakos, P., Pouli, N. & Papakonstantinou-Garoufalias. C. (2002). Synthesis and antiviral activity evaluation of some new 6-substituted-3-(1-adamantyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles. Farmaco, 57, 253-257. Pir, H., Günay, N., Tamer, Ö., Avcı, D. & Atalay, Y. (2013). Theoretical investigation of 5-(2-Acetoxyethyl)-6-methylpyrimidin-2, 4-dione: Conformational study, NBO and NLO analysis, molecular structure and NMR spectra, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 112, 331-342. Rani, A. U., Sundaraganesan, N., Kurt, M., Çınar, 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, 1523-1529. Rohling, C. M., Allen, L. C., & Ditchfield, R. (1984). Proton and C-13 chemical-shifts-comparison between theory and experiment. Chemical Physics, 87, 9-15. Sancak, K., Unver, Y., Kazak, C., Dugdu, E., and Arslan, B. (2010). Synthesis and characterizations 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. Sebag, A. B., Forsyth, D.A. & Plante, M. A. (2001). Conformation and configuration of tertiary amines via GIAO-derived (13)C NMR chemical shifts and a multiple independent variable regression analysis. The Journal of Organic Chemistry, 66 (24), 7967-7973. 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, 8251-8260. 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 İncelenmesi, Iğdır University Journal of the Institute of Science and Technology, 9 (1), 512-521. 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, 8251-8260.

Evaluation of Theoretical and Experimental Spectroscopic Properties of 3- Methyl-4-[4-methoxy-3-(p-toluenesulfonyloxy)-benzylidenamino]-4,5- dihydro-1H-1,2,4-triazol-5-one

Year 2019, Volume: 7 , 363 - 370, 24.11.2019

Abstract

In this study, 3-methyl-4-[4-methoxy-3-(p-toluenesulfonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-one was synthesized according to literature. Experimental data were obtained from the literature. The synthesized title compound was optimized by using B3LYP/6-311G(d,p) basis set. 1H-NMR and 13C-NMR spectral data values were calculated according to the method of gauge including atomic orbital (GIAO) and continuous set of gauge transformations (CSGT) methods using the program package Gaussian G09W Software. 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. Also, the calculated IR data of compound were calculated in gas phase by using of 6-311G(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. The calculated and experimental results were exhibited a very good agreement.

References

  • Abramov, Yu. A., Volkov, A. V. & Coppens, P. (1999). On the evaluation of molecular dipole moments from multipole refinement of X-ray diffraction data. Chemical Physics Letters, 311 (1-2), 81-86. Aktaş Yokuş, A. (2012). Bazı Yeni 1,2,4-Triazol Türevlerinin Sentezi ve Biyolojik Aktivitelerinin İncelenmesi. Doktora Tezi, Kafkas Üniversitesi Fen Bilimleri Enstitüsü, Kars. Becke A. D. (1993). Density functional thermochemistry. III. The role of exact Exchange, The Journal of Chemical Physics, 98, 5648-5652. Beytur, M., Turhan Irak, Z., Manap, S., and 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, 1-8. Cheeseman, J. R., Trucks, G. W., Keith, T. A. & Frisch. M. J. (1996). A comparison of models for calculating nuclear magnetic resonance shielding tensors. The Journal of Chemical Physics, 104 (14), 5497. 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. Ditchfield, R. (1974). Self-consistent perturbation theory of diamagnetism. Molecular Physics, 27 (4), 789-807. Frisch, M. J., Trucks, G., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J. A., Jr. Vreven, T., Peralta, J. E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, N., Staroverov, V. N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M., Knox, J. E., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Martin, L. R., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J., Dapprich, S., Daniels, A. D., Farkas, O., Foresman, J. B., Ortiz, J. V., Cioslowski, J. & Fox, D. J. (2009). Gaussian Inc., Wallingford, CT. Friesner, R. A., Murphy, R. B., Beachy, M. D., Ringnalda, M. N., Pollard, W. T., Dunietz, B.D. & Cao, Y. (1999). Correlated ab Initio Electronic Structure Calculations for Large Molecules, The Journal of Physical Chemistry A, 103 (13), 1913-1928. Forsyth, D. A. & Sebag. A. B. (1997). Computed 13C NMR Chemical Shifts via Empirically Scaled GIAO Shieldings and Molecular Mechanics Geometries. Conformation and Configuration from 13C Shifts, Journal of the American Chemical Society, 119 (40), 9483-9494. Gürsoy Kol, Ö., and 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. Handy, N. C., Maslen, P. E., Amons, R. D., Audrows, J. S., Murroy, C. W. & Lawing, G. (1992). The harmonic frequencies of benzene. Chemical Physics Letters, 197 (4-5), 506-515. Holla, B.S., Poojary, K.N., Rao, B.S. & Shivananda, M. K.. (2002). New bis-aminomercaptotriazoles and bis-triazolothiadiazoles as possible anticancer agents. European Journal of Medicinal Chemistry, 37 (6), 511-517. Jamróz, M. H. (2004). Vibrational Energy Distribution Analysis: VEDA 4 program, Warsaw. 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. Li, W., Wu, Q., Ye, Y., Luo, M., Hu, L., Gu, Y. & Niu. F. (2004). Density functional theory and ab initio studies of geometry, electronicstructure and vibrational spectra of novel benzothiazoleand benzotriazole herbicides. Spectrochimica Acta Part A, 60, 2343-2353. Keith, T. A., Bader, R. F. W., (2002). Calculation of magnetic response properties using a continuous set of gauge transformations. Chemical Physics Letters, 210 (1-3), 223-231. Kritsanida, M., Mouroutsou, A., Marakos, P., Pouli, N. & Papakonstantinou-Garoufalias. C. (2002). Synthesis and antiviral activity evaluation of some new 6-substituted-3-(1-adamantyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles. Farmaco, 57, 253-257. Pir, H., Günay, N., Tamer, Ö., Avcı, D. & Atalay, Y. (2013). Theoretical investigation of 5-(2-Acetoxyethyl)-6-methylpyrimidin-2, 4-dione: Conformational study, NBO and NLO analysis, molecular structure and NMR spectra, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 112, 331-342. Rani, A. U., Sundaraganesan, N., Kurt, M., Çınar, 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, 1523-1529. Rohling, C. M., Allen, L. C., & Ditchfield, R. (1984). Proton and C-13 chemical-shifts-comparison between theory and experiment. Chemical Physics, 87, 9-15. Sancak, K., Unver, Y., Kazak, C., Dugdu, E., and Arslan, B. (2010). Synthesis and characterizations 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. Sebag, A. B., Forsyth, D.A. & Plante, M. A. (2001). Conformation and configuration of tertiary amines via GIAO-derived (13)C NMR chemical shifts and a multiple independent variable regression analysis. The Journal of Organic Chemistry, 66 (24), 7967-7973. 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, 8251-8260. 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 İncelenmesi, Iğdır University Journal of the Institute of Science and Technology, 9 (1), 512-521. 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, 8251-8260.
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Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Murat Beytur

Haydar Yuksek

Publication Date November 24, 2019
Published in Issue Year 2019Volume: 7

Cite

APA Beytur, M., & Yuksek, H. (2019). Evaluation of Theoretical and Experimental Spectroscopic Properties of 3- Methyl-4-[4-methoxy-3-(p-toluenesulfonyloxy)-benzylidenamino]-4,5- dihydro-1H-1,2,4-triazol-5-one. The Eurasia Proceedings of Science Technology Engineering and Mathematics, 7, 363-370.