Araştırma Makalesi
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Yıl 2019, Cilt: 6 Sayı: 2, 76 - 98, 27.12.2019

Öz

Kaynakça

  • Akın Ş., Demir E.A., Colak A., Kolcuoglu Y., Yildirim N., Bekircan O. (2019). Synthesis, biological activities and molecular docking studies of some novel 2,4,5-trisubstituted-1,2,4-triazole-3-one derivatives as potent tyrosinase inhibitors. Journal of Molecular Structure, 1175, 280-286.
  • Akyıldırım O., Gökce H., Bahçeli S., Yüksek H. (2016). Theoretical and spectroscopic (FT-IR, NMR and UV–Vis.) characterizations of 3-p chlorobenzyl-4-(4-carboxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one molecule. Journal of Molecular Structure, 1127, 114-123.
  • Beytur M., Manap S., Özdemir, G., Gürsoy Kol, Ö., Aytemiz, F., Alkan, M., Yüksek, H., Preparation of Some New Bis-[4-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl)-azomethinphenyl] Phtalate Derivatives with Their Antioxidant and Antimicrobial Activities. Research Journal of Pharmaceutical Biological and Chemical Sciences, 10 (1), 426-436.
  • Boursas, F., Berrah, F., Kanagathara, N., Anbalagan, G. & Bouacida, S. (2019). XRD, FT-IR, FT-Raman spectra and ab initio HF vibrational analysis of bis (5-amino-3-carboxy-1H-1,2,4-triazol-4-ium) selenate dihydrate. Journal of Molecular Structure, 1180, 532-541.
  • Cui D., Li Z., Song G., Qian X. (2002). Synthesis and biological activities of N-(1,2,4-triazole-4-yl)-N′-(fluorine-containing-phenyl)carbamimidothioates. Journal of Fluorine Chemistry, 115(1), 79-82.
  • Du H., Fan Z., Yang L., Bao X. (2018). Synthesis and Antimicrobial Activities of Novel 1, 2, 4-Triazole-acyl-hydrazone Derivatives Containing the Quinazolin-4-one Moiety. Chinese Journal of Organic Chemistry, 8(2), 531-538.
  • Fukui K., Yonezawa T., Shingu H.J. (1952). A molecular orbital theory of reactivity in aromatic hydrocarbons, The Journal of Chemical Physics. 20, 722-725.
  • Frisch M.J., Trucks G.W., 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., Peralta J.E., Ogliaro F., Bearpark M., Heyd J.J., Brothers E., Kudin K.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 R.L., Morokuma K., Zakrzewski V.G., Voth G.A., Salvador P., Dannenberg J.J., Dapprich S., Daniels A.D., Foresman Farkas J.B., Ortiz J.V., Cioslowski J. Fox D.J. (2010). Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford CT,
  • Gao F., Wang T., Xiao J., Huang G. (2019). Antibacterial activity study of 1,2,4-triazole derivatives. European Journal of Medicinal Chemistry, 173, 274-281.
  • Irak Z.T., Beytur M. (2019). 4-Benzilidenamino-4,5-dihidro-1H-1,2,4-triazol-5-on Türevlerinin Antioksidan Aktivitelerinin Teorik Olarak İncelenmesi. Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 9(1), 512-521.
  • Jiao S., Wang, Z., Zhao Q., n Yu, W., Chang J. (2018). Synthesis of fused 3-amino-1,2,4-triazoles via sequential addition of aryl hydrazines to isothiocyanates and I2-mediated cyclodesulfurization. Tetrahedron, 74(24), 3069-3073.
  • Ocak N., Çoruh U., Kahveci B., Şaşmaz S., Vazquez-Lopez E.M., Erdönmez A. (2003). 1- Acetyl-3-(p-chlorobenzyl)-4-(p-chlorobenzylidenamino)-4,5-dihydro-1H-1,2,4- triazol-5-one. Acta Crystallographica Section E. 59(6), 750-752.
  • Özdemir G., Kotan G., Yüksek H., (2018). Theoretical Investigation of Spectroscopic, Electronic and Thermodynamic Properties of [2-Methoxy-4-(3-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethinphenyl] Acetate Molecule. Asian Journal of Chemical Sciences, 4, 1-12.
  • Özil M., Balaydın H.T. Şentürk M. (2019). Synthesis of 5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one’s aryl Schiff base derivatives and investigation of carbonic anhydrase and cholinesterase (AChE, BuChE) inhibitory properties. Bioorganic Chemistry, 86, 705–713.
  • Kotan G., Yüksek H., (2018). Investigation of Theoretical Properties of Novel 1-(Morpholine-4-yl-Methyl)-3-Methyl-4-(4-Ethoxybenzylidenamino)-4, 5-Dihydro-1H-1, 2, 4-Triazol-5-One Molecule. International Journal of Pharmaceutical, Chemical & Biological Sciences, 8(1). 147-156.
  • Kukuljan L. and Kranjc K. (2019). 3-(5-Amino-1,2,4-triazole)-1,2,4-oxadiazole: A new biheterocyclic scaffold for the synthesis of energetic materials. Tetrahedron Letters, 60, 207–209.
  • Madeira C.L., Field A. J., Simonich T.M., Tanguay R. L., Chorover J., Sierra-Alvarez R. (2018). Ecotoxicity of the insensitive munitions compound 3-nitro-1,2,4-triazol-5-one (NTO) and its reduced metabolite 3-amino-1,2,4-triazol-5-one (ATO). Journal of Hazardous Materials, 343, 340-346.
  • Mohameda N.G., Shehaa M.M., Hassana H.Y., Abdel-Hafezb L.J.M., Omarc F.A. (2018). Synthesis, antimicrobial activity and molecular modeling study of 3-(5-amino-(2H)-1,2,4-triazol-3-yl]-naphthyridinones as potential DNA-gyrase inhibitors. Bioorganic Chemistry, 81, 599–611.
  • Medetalibeyoğlu, H., (2015). Bazı yeni 4-[3-(3-metoksibenzoksi)-benzilidenamino]-4,5dihidro-1H-1,2,4-triazol-5-on türevlerinin sentezi, deneysel ve teorik özelliklerinin incelenmesi. Doktora Tezi, Kafkas Üniversitesi Fen Bilimleri Enstitüsü, Kimya Anabilim Dalı, Kars.
  • Merrick J.P., Moran D., Radom L. (2007). An Evaluation of Harmonic Vibrational Frequency Scale Factors. Journal of Physical Chemistry, 111(45), 11683-11700.
  • Raouf H., Beyramabadi, S.A., Allameh, S., Morsali, A. (2019). Synthesis, experimental and theoretical characterizations of a 1,2,4-triazole Schiff base and its nickel(II) complex. Journal of Molecular Structure, 1179, 779-786.
  • Saadaoui I., Krichen F., Salah B.B., Mansour R.B., Miled N., Bougatef A., Kossentini M. (2019). Design, synthesis and biological evaluation of Schiff bases of 4-amino-1,2,4-triazole derivatives as potent angiotensin converting enzyme inhibitors and antioxidant activities. Journal of Molecular Structure, 1180, 2019, 344-354.
  • Ustabas R., Çoruh U., Sancak K., Ünver Y., Vazquez-Lopez EM. (2007). 1-(benzoylmethyl)-4-[(2,4-dichlorobenzylidene)amino]-3-(2-thienylmethyl)4,5-dihydro-1H-1,2,4-triazol-5-one. Acta Crystallographica Section E. 63, 2982- 3051.
  • 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.
  • Yüksek H., Akyıldırım, O., Yola M.L., Gürsoy‐Kol Ö., Çelebier M., Kart, D. (2013). Synthesis, In Vitro Antimicrobial and Antioxidant Activities of Some New 4,5‐Dihydro‐1H‐1,2,4‐triazol‐5‐one Derivatives. Archiv der Pharmazie, 346 (6), 470-480.

Spectroscopic Aspects (Experimental/Theoretical (FT-IR, NMR)) and Electronic Properties of 3-p-Chlorobenzyl-4-[3-(3-methoxybenzoxy)- benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-one

Yıl 2019, Cilt: 6 Sayı: 2, 76 - 98, 27.12.2019

Öz








3-p-Chlorobenzyl-4-[3-(3-methoxybenzoxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-one were optimized
using DFT(B3LYP)/HF methods and 6-311G(d) and 3-21G levels. The
13C-NMR and 1H-NMR (in gas
phase/DMSO solvent with GIAO method), FT-IR and UV-vis spectral values were
performed using Gaussian09W program package. Theoretical spectral values of
the molecule were calculated and compared with experimental data.   The FT-IR spectrums were drawn the same
methods and levels. Furthermore,  the molecular potential surfaces such as
the molecular electrostatic potential (MEP),  electron density, electron spin potential (ESP), total density and contour maps of titled molecule have been drawn. The
electron affinity (A), electronegativity (χ), global hardness (η)/softness
(σ), ionization potential (I), E
LUMO-EHOMO energies,
energy gap (ΔE), thermal capacity (CV), mulliken atomic charges, entropy (S),
total energy,
 thermal energies (E),  bond angles, dipole
moments and bond lengths of the molecule were performed with Gaussian09W
program.








Kaynakça

  • Akın Ş., Demir E.A., Colak A., Kolcuoglu Y., Yildirim N., Bekircan O. (2019). Synthesis, biological activities and molecular docking studies of some novel 2,4,5-trisubstituted-1,2,4-triazole-3-one derivatives as potent tyrosinase inhibitors. Journal of Molecular Structure, 1175, 280-286.
  • Akyıldırım O., Gökce H., Bahçeli S., Yüksek H. (2016). Theoretical and spectroscopic (FT-IR, NMR and UV–Vis.) characterizations of 3-p chlorobenzyl-4-(4-carboxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one molecule. Journal of Molecular Structure, 1127, 114-123.
  • Beytur M., Manap S., Özdemir, G., Gürsoy Kol, Ö., Aytemiz, F., Alkan, M., Yüksek, H., Preparation of Some New Bis-[4-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl)-azomethinphenyl] Phtalate Derivatives with Their Antioxidant and Antimicrobial Activities. Research Journal of Pharmaceutical Biological and Chemical Sciences, 10 (1), 426-436.
  • Boursas, F., Berrah, F., Kanagathara, N., Anbalagan, G. & Bouacida, S. (2019). XRD, FT-IR, FT-Raman spectra and ab initio HF vibrational analysis of bis (5-amino-3-carboxy-1H-1,2,4-triazol-4-ium) selenate dihydrate. Journal of Molecular Structure, 1180, 532-541.
  • Cui D., Li Z., Song G., Qian X. (2002). Synthesis and biological activities of N-(1,2,4-triazole-4-yl)-N′-(fluorine-containing-phenyl)carbamimidothioates. Journal of Fluorine Chemistry, 115(1), 79-82.
  • Du H., Fan Z., Yang L., Bao X. (2018). Synthesis and Antimicrobial Activities of Novel 1, 2, 4-Triazole-acyl-hydrazone Derivatives Containing the Quinazolin-4-one Moiety. Chinese Journal of Organic Chemistry, 8(2), 531-538.
  • Fukui K., Yonezawa T., Shingu H.J. (1952). A molecular orbital theory of reactivity in aromatic hydrocarbons, The Journal of Chemical Physics. 20, 722-725.
  • Frisch M.J., Trucks G.W., 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., Peralta J.E., Ogliaro F., Bearpark M., Heyd J.J., Brothers E., Kudin K.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 R.L., Morokuma K., Zakrzewski V.G., Voth G.A., Salvador P., Dannenberg J.J., Dapprich S., Daniels A.D., Foresman Farkas J.B., Ortiz J.V., Cioslowski J. Fox D.J. (2010). Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford CT,
  • Gao F., Wang T., Xiao J., Huang G. (2019). Antibacterial activity study of 1,2,4-triazole derivatives. European Journal of Medicinal Chemistry, 173, 274-281.
  • Irak Z.T., Beytur M. (2019). 4-Benzilidenamino-4,5-dihidro-1H-1,2,4-triazol-5-on Türevlerinin Antioksidan Aktivitelerinin Teorik Olarak İncelenmesi. Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 9(1), 512-521.
  • Jiao S., Wang, Z., Zhao Q., n Yu, W., Chang J. (2018). Synthesis of fused 3-amino-1,2,4-triazoles via sequential addition of aryl hydrazines to isothiocyanates and I2-mediated cyclodesulfurization. Tetrahedron, 74(24), 3069-3073.
  • Ocak N., Çoruh U., Kahveci B., Şaşmaz S., Vazquez-Lopez E.M., Erdönmez A. (2003). 1- Acetyl-3-(p-chlorobenzyl)-4-(p-chlorobenzylidenamino)-4,5-dihydro-1H-1,2,4- triazol-5-one. Acta Crystallographica Section E. 59(6), 750-752.
  • Özdemir G., Kotan G., Yüksek H., (2018). Theoretical Investigation of Spectroscopic, Electronic and Thermodynamic Properties of [2-Methoxy-4-(3-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethinphenyl] Acetate Molecule. Asian Journal of Chemical Sciences, 4, 1-12.
  • Özil M., Balaydın H.T. Şentürk M. (2019). Synthesis of 5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one’s aryl Schiff base derivatives and investigation of carbonic anhydrase and cholinesterase (AChE, BuChE) inhibitory properties. Bioorganic Chemistry, 86, 705–713.
  • Kotan G., Yüksek H., (2018). Investigation of Theoretical Properties of Novel 1-(Morpholine-4-yl-Methyl)-3-Methyl-4-(4-Ethoxybenzylidenamino)-4, 5-Dihydro-1H-1, 2, 4-Triazol-5-One Molecule. International Journal of Pharmaceutical, Chemical & Biological Sciences, 8(1). 147-156.
  • Kukuljan L. and Kranjc K. (2019). 3-(5-Amino-1,2,4-triazole)-1,2,4-oxadiazole: A new biheterocyclic scaffold for the synthesis of energetic materials. Tetrahedron Letters, 60, 207–209.
  • Madeira C.L., Field A. J., Simonich T.M., Tanguay R. L., Chorover J., Sierra-Alvarez R. (2018). Ecotoxicity of the insensitive munitions compound 3-nitro-1,2,4-triazol-5-one (NTO) and its reduced metabolite 3-amino-1,2,4-triazol-5-one (ATO). Journal of Hazardous Materials, 343, 340-346.
  • Mohameda N.G., Shehaa M.M., Hassana H.Y., Abdel-Hafezb L.J.M., Omarc F.A. (2018). Synthesis, antimicrobial activity and molecular modeling study of 3-(5-amino-(2H)-1,2,4-triazol-3-yl]-naphthyridinones as potential DNA-gyrase inhibitors. Bioorganic Chemistry, 81, 599–611.
  • Medetalibeyoğlu, H., (2015). Bazı yeni 4-[3-(3-metoksibenzoksi)-benzilidenamino]-4,5dihidro-1H-1,2,4-triazol-5-on türevlerinin sentezi, deneysel ve teorik özelliklerinin incelenmesi. Doktora Tezi, Kafkas Üniversitesi Fen Bilimleri Enstitüsü, Kimya Anabilim Dalı, Kars.
  • Merrick J.P., Moran D., Radom L. (2007). An Evaluation of Harmonic Vibrational Frequency Scale Factors. Journal of Physical Chemistry, 111(45), 11683-11700.
  • Raouf H., Beyramabadi, S.A., Allameh, S., Morsali, A. (2019). Synthesis, experimental and theoretical characterizations of a 1,2,4-triazole Schiff base and its nickel(II) complex. Journal of Molecular Structure, 1179, 779-786.
  • Saadaoui I., Krichen F., Salah B.B., Mansour R.B., Miled N., Bougatef A., Kossentini M. (2019). Design, synthesis and biological evaluation of Schiff bases of 4-amino-1,2,4-triazole derivatives as potent angiotensin converting enzyme inhibitors and antioxidant activities. Journal of Molecular Structure, 1180, 2019, 344-354.
  • Ustabas R., Çoruh U., Sancak K., Ünver Y., Vazquez-Lopez EM. (2007). 1-(benzoylmethyl)-4-[(2,4-dichlorobenzylidene)amino]-3-(2-thienylmethyl)4,5-dihydro-1H-1,2,4-triazol-5-one. Acta Crystallographica Section E. 63, 2982- 3051.
  • 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.
  • Yüksek H., Akyıldırım, O., Yola M.L., Gürsoy‐Kol Ö., Çelebier M., Kart, D. (2013). Synthesis, In Vitro Antimicrobial and Antioxidant Activities of Some New 4,5‐Dihydro‐1H‐1,2,4‐triazol‐5‐one Derivatives. Archiv der Pharmazie, 346 (6), 470-480.
Toplam 25 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Çevre Bilimleri
Bölüm Makaleler
Yazarlar

Hilal Medetalibeyoğlu 0000-0002-1310-6811

Haydar Yüksek Bu kişi benim 0000-0003-1289-1800

Yayımlanma Tarihi 27 Aralık 2019
Gönderilme Tarihi 22 Mayıs 2019
Kabul Tarihi 25 Kasım 2019
Yayımlandığı Sayı Yıl 2019 Cilt: 6 Sayı: 2

Kaynak Göster

APA Medetalibeyoğlu, H., & Yüksek, H. (2019). Spectroscopic Aspects (Experimental/Theoretical (FT-IR, NMR)) and Electronic Properties of 3-p-Chlorobenzyl-4-[3-(3-methoxybenzoxy)- benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-one. Caucasian Journal of Science, 6(2), 76-98.

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