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3-Metil-4-(3-metil-2-tiyenilmetilenamino)-4,5-dihidro-1H-1,2,4- triazol-5-one molekülünün elektronik, geometrik ve spektroskopik özelliklerinin incelenmesi

Year 2018, Issue: 3, 20 - 26, 31.12.2018

Abstract

3-Metil-4-(3-metil-2-tiyenilmetilenamino)-4,5-dihidro-1H-1,2,4-triazol-5-on molekülü HF/ B3LYP6-311G(d,p) temel setleri kullanılarak optimize edilmiştir. Sonra, Gaussian 09W paket programı kullanılarak GIAO metoduna göre 1 H- ve 13C-NMR isotropik kayma değerleri hesaplanmıştır. Teorik ve deneysel değerler δ exp=a+b. δ calc. eşitliğine göre grafiğe geçirilmiştir. Standart hata değerleri a, b sabitlerinin regresyon katsayısı ile Sigmaplot programı kullanılarak bulunmuştur. Ayrıca, Veda 4f programı teorik olarak IR verilerini belirlemede kullanılmıştır. DFT ve HF metodları ile elde edilen veriler teorik infrared spectrumu çizilmesinde kullanılmıştır. Ek olarak, geometrik özellikler (bağ uzunlukları ve açıları, mulliken atomik yükleri), elektronik özellikler (ELUMO-EHOMO kapasitesi (ΔEg), elektronegatiflik (χ), elektron yoğunluğu (A), global sertlik (η), yumuşaklık (σ), iyonizasyon potansiyeli (I), molekülün toplam enerjisi, dipol moment), termodinamik özellikleri, HOMO ve LUMO, Gaussian 09W paket programı kullanılarak hesaplanmıştır.

References

  • Puchtler, Meloan S. On schiff's bases and aldehyde-Fuchsin: a review from H. Schiff to RD Lillie, Histochem. Cell Biol., 1981, 72 (3) 321-332.
  • Gao, W.T., Zheng, Z. Synthetic studies on optically active Schiff-base ligands derived from condensation of 2-hydroxyacetophenone and chiral diamines, Molecules, 2002, 7 (7) 511-516.
  • Shakir, M., Azam, M., Azim, Y., Parveen, S., Khan, A.U. Synthesis and physico-chemical studies on complexes of 1, 2-diaminophenyl-N, N-bis-(2-pyr-idinecarboxaldimine),(L): a spectroscopic approach on binding studies of DNA with the copper complex, Polyhedron, 2007, 26 (18) 5513-5518.
  • Aydogan, F., Ocal, N., Turgut, Z., Yolacan, C. Transformations of aldimines derived from pyrrole-2-Synthesis of thiazolidino-fused compounds, Bull. Korean Chem. Soc., 2001, 22 (5) 476-480.
  • Azam, F., Singh, S., Khokhra, S.L., Prakash, O. Synthesis of Schiff bases of naphtha[1, 2 d] thiazol-2-amine and metal complexes of 2-(2-hydroxy) benzylide-neaminonaphthothiazole as potential antimicrobial agents, J. Zhejiang Univ.Sci. 2007, B 8 (6) 446-452.
  • Young, D.W. Heterocyclic Chemistry, first ed., Longman group Ltd., London, 1975.
  • Kumar, K.S., Ganguly, S., Veerasamy, R., De Clercq, E. Synthesis, antiviral activity and cytotoxicity evaluation of Schiff bases of some 2-phenyl quinazoline-4(3)H-ones, Eur. J. Med. Chem., 2010, 45 (11) 5474-5479.
  • Günor, O., Gürkan, P. Synthesis and characterization of higher amino acid Schiff bases, as monosodium salts and neutral forms. Investigation of the intramolecular hydrogen bonding in all Schiff bases, antibacterial and anti-fungal activities of neutral forms, J. Mol. Struct., 2014, 1074 62-70.
  • Shanty, A.A., Philip, J.E., Sneha, E.J., Kurup, M.R.P., Balachandran, S., Mohanan, P.V. Synthesis, characterization and biological studies of Schiff bases derived from heterocyclic moiety, Bioorg. Chem., 2017, 70 67-73.
  • Pontiki, E., Hadjipavlou-Litina, D., Chaviara, A. Evaluation of anti-inflammatory and antioxidant activities of copper (II) Schiff mono-base and copper (II) Schiff base coordination compounds of dien with heterocyclic aldehydes and 2-amino-5 methylthiazole, J. Enzym. Inhib. Med. Chem., 2008, 23 (6) 1011-1017.
  • Amer, S., El-Wakiel, N., El-Ghamry, H. Synthesis, spectral, antitumor and antimicrobial studies on Cu (II) complexes of purine and triazole Schiff base derivatives, J. Mol. Struct., 2013, 1049 326-335.
  • El-wakiel, N., El-keiy, M., Gaber, M. Synthesis, spectral, antitumor, antioxidant and antimicrobial studies on Cu (II), Ni (II) and Co (II) complexes of 4-[(1HBenzoimidazol 2-ylimino)-methyl]-benzene-1, 3-diol, Spectrochim. Acta Mol. Biomol. Spectrosc., 2015, 147 117-123.
  • Bensaber, S.M., Allafe, H., Ermeli, N.B., Mohamed, S.B., Zetrini, A.A., Alsabri, S.G., Erhuma, M., Hermann, A., Jaeda, M.I., Gbaj, A.M. Chemical synthesis, molecular modelling, and evaluation of anticancer activity of some pyrazol-3-one Schiff base derivatives, Med. Chem. Res., 2014, 23 (12) 5120-5134.
  • Sinha, A., Banerjee, K., Banerjee, A., Das, S., Choudhuri, S.K. Synthesis, charac-terization and biological evaluation of a novel vanadium complex as a possible anticancer agent, J. Organomet. Chem., 2014, 772 34-41.
  • Pramanik H.A., Das, D., Paul, P.C., Mondal, P., Bhattacharjee, C.R. Newer mixed ligand Schiff base complexes from aquo-N-(2-hydroxy acetophenone) glyci-natocopper (II) as synthon: DFT, antimicrobial activity and molecular docking study, J. Mol. Struct., 2014, 1059 309-319.
  • Da Silva, C.M., Da Silva, D.L., Modolo, L.V., Alves, R.B., De Resende M.A., Martins, C.V., De Fatima, A. Schiff bases: a short review of their antimicrobial activities, J. Adv. Res., 2011, 2 (1) 1-8.
  • Chinnasamy, R.P., Sundararajan, R., Govindaraj, S. Synthesis, haracterization, and analgesic activity of novel schiff base of isatin derivatives, J. Adv. Pharm. Technol. Res. (JAPTR), 2010, 1 (3) 342.
  • Yüksek, H., Gürsoy, Ö., Çakmak, İ. and Alkan, M. Synthesis and GIAO NMR Calculation for Some New 4,5-Dihydro-1H-1,2,4-triazol-5-one Derivatives: Comparison of Theoretical and Experimental 1H and 13C Chemical Shifts Magn. Reson. Chem., 2005, 43 585-587.
  • Yüksek, H., Çakmak, İ., Sadi, S., Alkan, M. and Baykara, H. Synthesis and GIAO NMR Calculations for Some Novel 4-Heteroarylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives: Comparison of Theoretical and Experimental 1H and 13C Chemical Shifts Int. J. Mol. Sci., 2005, 6 219-229.
  • Yüksek, H., Alkan, M., Bahçeci, Ş., Çakmak, İ., Ocak, Z., Baykara, H., Aktaş, Ö. And Ağyel, E. Synthesis, Determination of pKa Values and GIAO NMR Calculations of Some New 3-Alkyl-4-(p-methoxybenzoylamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones J. Mol. Struc., 2008, 873 142-148.
  • Yüksek, H., Alkan, M., Çakmak, İ., Ocak, Z., Bahçeci, Ş., Calapoğlu, M., Elmastaş, M., Kolomuç A. and Aksu H. Preparation, GIAO NMR calculations and acidic properties of some novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives with their antioxidant activities Int. J. Mol. Sci., 2008, 9 12-32.
  • Gökçe, H., Bahçeli, S., Akyıldırım, O., Yüksek, H. and Gürsoy-Kol, Ö. The Syntheses, Molecular Structures, Spectroscopic Properties (IR, Micro-Raman, NMR and UV–vis) and DFT Calculations of Antioxidant 3-alkyl-4-[3-methoxy-4-(4-methylbenzoxy)benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-one Molecules Letters in Organic Chemistry, 2013, 10 (6): 395-441.
  • Gökçe, H., Akyıldırım, O., Bahçeli, S., Yüksek, H. and Gürsoy-Kol, Ö. The 1-acetyl-3-methyl-4-[3-methoxy-4-(4-methylbenzoxy)benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-one Molecule Investigated by a Joint Spectroscopic and Quantum Chemical Calculations Journal of Molecular: http://dx.doi.org/10.1016/j.molstruc. (2013).10.044, 1056-1057: 273-284.
  • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., et al. Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford, CT., 2009.
  • Wolinski, K., Hilton, J.F. and Pulay, P.J. Am. Chem. Soc. 1990, 112, 512.
  • Jamróz, M.H. Vibrational Energy Distribution Analysis: VEDA 4 program, Warsaw, 2004.
  • Gürsoy-Kol, Ö., Yüksek, H., İslamoğlu, F., Journal of the Chemical Society of Pakistan, 2013, 35(4), 1179-1190.
  • Merrick, J.P, Moran, D., Radom, L. An Evaluation of Harmonic Vibrational Frequency Scale Factors.Journal of Physical Chemistry, 2007, 111 (45), 11683-11700.

Investigation of Electronic, Geometric and Spectroscopic Properties of 3-Methyl-4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one Molecule

Year 2018, Issue: 3, 20 - 26, 31.12.2018

Abstract

3-Methyl-4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one molecule was optimized by using the DFT/6311G
(d,p) and HF/6311G (d,p) basis sets. Afterwards,
1H-NMR and 13C-NMR
isotropic shift values were calculated by the method of GIAO using the program
package Gaussian G09W. Theoretical and experimental values were inserted into
the graphic according to equitation of δ exp=a+b. δ calc. The standard error
values were found via SigmaPlot program with regression coefficient of a and b
constants. Furthermore, the veda4f program was used in defining of IR data
theoretically. The data obtained  with
using HF and DFT method are formed using theoretical infrared spectrum.
In addition, geometric properties (bond lengths and angles),
electronic properties (
ELUMO-EHOMO (ΔEg),
ionization potential (I), electronegativity (χ), global hardness (η), electron
affinity (A), softness (σ),
dipole
moment,
mulliken atomic charges, total
energy of the molecule
),
thermodynamics properties, HOMO and LUMO, have been calculated by using Gaussian
09W program.

References

  • Puchtler, Meloan S. On schiff's bases and aldehyde-Fuchsin: a review from H. Schiff to RD Lillie, Histochem. Cell Biol., 1981, 72 (3) 321-332.
  • Gao, W.T., Zheng, Z. Synthetic studies on optically active Schiff-base ligands derived from condensation of 2-hydroxyacetophenone and chiral diamines, Molecules, 2002, 7 (7) 511-516.
  • Shakir, M., Azam, M., Azim, Y., Parveen, S., Khan, A.U. Synthesis and physico-chemical studies on complexes of 1, 2-diaminophenyl-N, N-bis-(2-pyr-idinecarboxaldimine),(L): a spectroscopic approach on binding studies of DNA with the copper complex, Polyhedron, 2007, 26 (18) 5513-5518.
  • Aydogan, F., Ocal, N., Turgut, Z., Yolacan, C. Transformations of aldimines derived from pyrrole-2-Synthesis of thiazolidino-fused compounds, Bull. Korean Chem. Soc., 2001, 22 (5) 476-480.
  • Azam, F., Singh, S., Khokhra, S.L., Prakash, O. Synthesis of Schiff bases of naphtha[1, 2 d] thiazol-2-amine and metal complexes of 2-(2-hydroxy) benzylide-neaminonaphthothiazole as potential antimicrobial agents, J. Zhejiang Univ.Sci. 2007, B 8 (6) 446-452.
  • Young, D.W. Heterocyclic Chemistry, first ed., Longman group Ltd., London, 1975.
  • Kumar, K.S., Ganguly, S., Veerasamy, R., De Clercq, E. Synthesis, antiviral activity and cytotoxicity evaluation of Schiff bases of some 2-phenyl quinazoline-4(3)H-ones, Eur. J. Med. Chem., 2010, 45 (11) 5474-5479.
  • Günor, O., Gürkan, P. Synthesis and characterization of higher amino acid Schiff bases, as monosodium salts and neutral forms. Investigation of the intramolecular hydrogen bonding in all Schiff bases, antibacterial and anti-fungal activities of neutral forms, J. Mol. Struct., 2014, 1074 62-70.
  • Shanty, A.A., Philip, J.E., Sneha, E.J., Kurup, M.R.P., Balachandran, S., Mohanan, P.V. Synthesis, characterization and biological studies of Schiff bases derived from heterocyclic moiety, Bioorg. Chem., 2017, 70 67-73.
  • Pontiki, E., Hadjipavlou-Litina, D., Chaviara, A. Evaluation of anti-inflammatory and antioxidant activities of copper (II) Schiff mono-base and copper (II) Schiff base coordination compounds of dien with heterocyclic aldehydes and 2-amino-5 methylthiazole, J. Enzym. Inhib. Med. Chem., 2008, 23 (6) 1011-1017.
  • Amer, S., El-Wakiel, N., El-Ghamry, H. Synthesis, spectral, antitumor and antimicrobial studies on Cu (II) complexes of purine and triazole Schiff base derivatives, J. Mol. Struct., 2013, 1049 326-335.
  • El-wakiel, N., El-keiy, M., Gaber, M. Synthesis, spectral, antitumor, antioxidant and antimicrobial studies on Cu (II), Ni (II) and Co (II) complexes of 4-[(1HBenzoimidazol 2-ylimino)-methyl]-benzene-1, 3-diol, Spectrochim. Acta Mol. Biomol. Spectrosc., 2015, 147 117-123.
  • Bensaber, S.M., Allafe, H., Ermeli, N.B., Mohamed, S.B., Zetrini, A.A., Alsabri, S.G., Erhuma, M., Hermann, A., Jaeda, M.I., Gbaj, A.M. Chemical synthesis, molecular modelling, and evaluation of anticancer activity of some pyrazol-3-one Schiff base derivatives, Med. Chem. Res., 2014, 23 (12) 5120-5134.
  • Sinha, A., Banerjee, K., Banerjee, A., Das, S., Choudhuri, S.K. Synthesis, charac-terization and biological evaluation of a novel vanadium complex as a possible anticancer agent, J. Organomet. Chem., 2014, 772 34-41.
  • Pramanik H.A., Das, D., Paul, P.C., Mondal, P., Bhattacharjee, C.R. Newer mixed ligand Schiff base complexes from aquo-N-(2-hydroxy acetophenone) glyci-natocopper (II) as synthon: DFT, antimicrobial activity and molecular docking study, J. Mol. Struct., 2014, 1059 309-319.
  • Da Silva, C.M., Da Silva, D.L., Modolo, L.V., Alves, R.B., De Resende M.A., Martins, C.V., De Fatima, A. Schiff bases: a short review of their antimicrobial activities, J. Adv. Res., 2011, 2 (1) 1-8.
  • Chinnasamy, R.P., Sundararajan, R., Govindaraj, S. Synthesis, haracterization, and analgesic activity of novel schiff base of isatin derivatives, J. Adv. Pharm. Technol. Res. (JAPTR), 2010, 1 (3) 342.
  • Yüksek, H., Gürsoy, Ö., Çakmak, İ. and Alkan, M. Synthesis and GIAO NMR Calculation for Some New 4,5-Dihydro-1H-1,2,4-triazol-5-one Derivatives: Comparison of Theoretical and Experimental 1H and 13C Chemical Shifts Magn. Reson. Chem., 2005, 43 585-587.
  • Yüksek, H., Çakmak, İ., Sadi, S., Alkan, M. and Baykara, H. Synthesis and GIAO NMR Calculations for Some Novel 4-Heteroarylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives: Comparison of Theoretical and Experimental 1H and 13C Chemical Shifts Int. J. Mol. Sci., 2005, 6 219-229.
  • Yüksek, H., Alkan, M., Bahçeci, Ş., Çakmak, İ., Ocak, Z., Baykara, H., Aktaş, Ö. And Ağyel, E. Synthesis, Determination of pKa Values and GIAO NMR Calculations of Some New 3-Alkyl-4-(p-methoxybenzoylamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones J. Mol. Struc., 2008, 873 142-148.
  • Yüksek, H., Alkan, M., Çakmak, İ., Ocak, Z., Bahçeci, Ş., Calapoğlu, M., Elmastaş, M., Kolomuç A. and Aksu H. Preparation, GIAO NMR calculations and acidic properties of some novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives with their antioxidant activities Int. J. Mol. Sci., 2008, 9 12-32.
  • Gökçe, H., Bahçeli, S., Akyıldırım, O., Yüksek, H. and Gürsoy-Kol, Ö. The Syntheses, Molecular Structures, Spectroscopic Properties (IR, Micro-Raman, NMR and UV–vis) and DFT Calculations of Antioxidant 3-alkyl-4-[3-methoxy-4-(4-methylbenzoxy)benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-one Molecules Letters in Organic Chemistry, 2013, 10 (6): 395-441.
  • Gökçe, H., Akyıldırım, O., Bahçeli, S., Yüksek, H. and Gürsoy-Kol, Ö. The 1-acetyl-3-methyl-4-[3-methoxy-4-(4-methylbenzoxy)benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-one Molecule Investigated by a Joint Spectroscopic and Quantum Chemical Calculations Journal of Molecular: http://dx.doi.org/10.1016/j.molstruc. (2013).10.044, 1056-1057: 273-284.
  • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., et al. Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford, CT., 2009.
  • Wolinski, K., Hilton, J.F. and Pulay, P.J. Am. Chem. Soc. 1990, 112, 512.
  • Jamróz, M.H. Vibrational Energy Distribution Analysis: VEDA 4 program, Warsaw, 2004.
  • Gürsoy-Kol, Ö., Yüksek, H., İslamoğlu, F., Journal of the Chemical Society of Pakistan, 2013, 35(4), 1179-1190.
  • Merrick, J.P, Moran, D., Radom, L. An Evaluation of Harmonic Vibrational Frequency Scale Factors.Journal of Physical Chemistry, 2007, 111 (45), 11683-11700.
There are 28 citations in total.

Details

Primary Language English
Subjects Electrochemistry
Journal Section Research Article
Authors

Gül Kotan 0000-0002-4507-9029

Önder Albayrak This is me 0000-0002-6573-6137

Haydar Yüksek This is me 0000-0003-1289-1800

Publication Date December 31, 2018
Published in Issue Year 2018 Issue: 3

Cite

APA Kotan, G., Albayrak, Ö., & Yüksek, H. (2018). Investigation of Electronic, Geometric and Spectroscopic Properties of 3-Methyl-4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one Molecule. Karadeniz Chemical Science and Technology(3), 20-26.
AMA Kotan G, Albayrak Ö, Yüksek H. Investigation of Electronic, Geometric and Spectroscopic Properties of 3-Methyl-4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one Molecule. Karadeniz Chem. Sci. Tech. December 2018;(3):20-26.
Chicago Kotan, Gül, Önder Albayrak, and Haydar Yüksek. “Investigation of Electronic, Geometric and Spectroscopic Properties of 3-Methyl-4-(3-Methyl-2-Thienylmethyleneamino)-4,5-Dihydro-1H-1,2,4-Triazol-5-One Molecule”. Karadeniz Chemical Science and Technology, no. 3 (December 2018): 20-26.
EndNote Kotan G, Albayrak Ö, Yüksek H (December 1, 2018) Investigation of Electronic, Geometric and Spectroscopic Properties of 3-Methyl-4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one Molecule. Karadeniz Chemical Science and Technology 3 20–26.
IEEE G. Kotan, Ö. Albayrak, and H. Yüksek, “Investigation of Electronic, Geometric and Spectroscopic Properties of 3-Methyl-4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one Molecule”, Karadeniz Chem. Sci. Tech., no. 3, pp. 20–26, December 2018.
ISNAD Kotan, Gül et al. “Investigation of Electronic, Geometric and Spectroscopic Properties of 3-Methyl-4-(3-Methyl-2-Thienylmethyleneamino)-4,5-Dihydro-1H-1,2,4-Triazol-5-One Molecule”. Karadeniz Chemical Science and Technology 3 (December 2018), 20-26.
JAMA Kotan G, Albayrak Ö, Yüksek H. Investigation of Electronic, Geometric and Spectroscopic Properties of 3-Methyl-4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one Molecule. Karadeniz Chem. Sci. Tech. 2018;:20–26.
MLA Kotan, Gül et al. “Investigation of Electronic, Geometric and Spectroscopic Properties of 3-Methyl-4-(3-Methyl-2-Thienylmethyleneamino)-4,5-Dihydro-1H-1,2,4-Triazol-5-One Molecule”. Karadeniz Chemical Science and Technology, no. 3, 2018, pp. 20-26.
Vancouver Kotan G, Albayrak Ö, Yüksek H. Investigation of Electronic, Geometric and Spectroscopic Properties of 3-Methyl-4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one Molecule. Karadeniz Chem. Sci. Tech. 2018(3):20-6.