Investigation of Some Theoretical Properties of 1-Methyl-3-phenyl-4-[3-(pnitrobenzoxy)benzylideneamino]-4,5-dihydro-1H-1,2,4-triazol-5-one

Year 2017, Volume: 10 Issue: 1, 25 - 36, 23.10.2017

Hilal Medetalibeyoğlu , Özlem Gürsoy Kol , Murat Beytur , Haydar Yüksek

Abstract

In this study, 1-methyl-3-phenyl-4-[3-(p-nitrobenzoxy)benzylidenamino]- 4,5-dihydro-1H-1,2,4-triazol-5-one was optimized by using the B3LYP/6-31G(d) and HF/6-31G(d) basis sets. 1H-NMR and 13C-NMR isotropic shift values were calculated by the method of GIAO using the program package Gaussian G09W. Experimental and theoretical values were inserted into the grafic according to equatation of δ exp=a+b. δ calc. The standard error values were found via SigmaPlot program with regression coefficient of a and b constants. IR absorption frequencies of this compound were also calculated by two methods. The Veda4f program was used in defining IR data which were calculated theoretically. Furthermore, bond angles, bond lengths, Mulliken atomic charges, HOMO-LUMO energies, dipole moments, total energies of 1-methyl-3- phenyl-4-[3-(p-nitrobenzoxy)benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-one have been investigated.

Keywords

1, 2, 4-Triazol-5-one, GIAO, B3LYP, HF, 6-31G(d)

1-Metil-3-fenil-4-[3-(p-nitrobenzoksi)benzilidenamino]-4,5-dihidro-1H-1,2,4- triazol-5-on Bileşiğinin Bazı Teorik Özelliklerinin İncelenmesi

Abstract

Bu
çalışmada, 1-metil-3-fenil-4-[3-(p-nitrobenzoksi)benzilidenamino]-4,5-dihidro-1H-1,2,4-triazol-5-on bileşiği
B3LYP/6-31G(d) ve HF/6-31G(d) temel setleri kullanılarak optimize edilmiştir. ¹H-NMR
ve ¹³C-NMR kimyasal kayma değerleri GIAO metoduyla Gaussian G09W
paket programı kullanılarak hesaplanmıştır. Deneysel ve teorik olarak bulunan
değerler δ exp=a+b. δ calc. eşitliğine göre grafiğe geçirilmiştir. Sigmaplot
programı kullanılarak a ve b sabitleri regresyon katsayısı ile standart hata
değerleri bulunmuştur. Bu bileşiğin IR frekans değerleri de aynı metodla
hesaplanmıştır. Teorik olarak hesaplanan IR verilerinin tanımlanmasında Veda4f
programı kullanılmıştır. İlaveten, 1-metil-3-fenil-4-[3-(p-nitrobenzoksi)benzilidenamino]-4,5-dihidro-1H-1,2,4-triazol-5-on bileşiğinin
bağ açıları, bağ uzunlukları, Mulliken atomik yükleri, HOMO-LUMO enerjileri,
dipol momentleri, toplam enerjileri incelenmiştir.

Keywords

1, 2, 4-Triazol-5-on, GIAO, B3LYP, HF, 6-31G(d)

References

• Apaydın F. (1991). Magnetik Rezonans, Hacettepe Üniversitesi, 3; 6-8.
• Denningto R., Keith T., Millam J. (2009). GaussView, Version 5, Semichem Inc., Shawnee Mission KS.
• Foresman J.B., Frisch Æ. (1996). Exploring Chemistry with electronic structure methods (2nd ed.), Pittsburgh, PA: Gaussian Inc., 266, 278–283.
• 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., Vreven T.Jr., 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.J., Ochterski 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).
• Gökçe H., Bahçeli S., Akyıldırım O., Yüksek H., Gürsoy Kol Ö. (2013). 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, 10; 395-441.
• Gökçe H., Akyıldırım O., Bahçeli S., Yüksek H., Gürsoy Kol,O. (2014). 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 Structure, 1056-1057; 273–284.
• Gümüş P.H., Tamer Ö., Avcı D., Atalay Y. (2015). 4-(Metoksimetil)-1,6-dimetil-2-okso-1,2-dihidropiridin-3-karbonitril molekülünün teorik olarak incelenmesi. Sakarya Üniversitesi Fen Bilimleri Dergisi, 3; 303-311.
• Gürsoy Kol Ö., Yüksek H., (2010). Synthesis and In-vitro Antioxidant Evaluation of Some Novel 4,5-Dihydro-1H-1,2,4-triazol-5-one Derivatives. E-Journal of Chemistry, 7 (1): 123-136.
• Merrick J.P., Moran D., Radom L. (2007). An Evaluation of Harmonic Vibrational Frequency Scale Factors. Journal of Physical Chemistry A, 111 (45); 11683-11700.
• Turhan Irak Z., Gümüş S. (2017). Heterotricyclic Compounds via Click Reaction: A Computational Study. Noble International Journal of Scientific Research, 1(7), 80-89.
• Yüksek H., Gürsoy Ö., Çakmak İ., Alkan M. (2005a). 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. Magnetic Resonance in Chemistry, 43; 585-587.
• Yüksek H., Çakmak İ., Sadi S., Alkan M. (2005b). 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. International Journal of Molecular Sciences, 6; 219-229.