Theoretical Investigation of 4-(Methoxymethyl)-1,6-Dimethyl-2-Oxo-1,2-Dihydropyridine-3-Carbonitrile Molecule

Year 2015, Volume: 19 Issue: 3, 303 - 311, 12.08.2015

Hacer Pir Gümüş , Ömer Tamer , Davut Avcı , Yusuf Atalay

https://doi.org/10.16984/saufenbilder.86449

Cited By: 4

Abstract

In present study, quantum chemistry calculations of geometric parameters, harmonic vibrational wavenumbers and the ¹H and ¹³C nuclear magnetic resonance (NMR) chemical shifts values of 4-(methoxymethyl)-1,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile [C₁₀H₁₂N₂O₂] molecule in the ground state were calculated using HF/6-311++G(d,p) and DFT/B3LYP/6-311++G(d,p) methods. The results of the optimized molecular structure were presented and compared with the experimental values. The observed and the calculated values were found to be in good agreement. In addition, nonlinear optical (NLO) analysis, the molecular frontier orbital energies, thermodynamic parameters, molecular surfaces, Mulliken, APT and NBO charges were investigated using HF and DFT quantum chemical calculations.

Keywords

4-(methoxymethyl)-1, 6-dimethyl-2-oxo-1, 2-dihydropyridine-3-carbonitrile, HF and DFT calculations, NLO analysis, molecular surface (MEP and ESP) maps

4-(Metoksimetil)-1,6-dimetil-2-okso-1,2-dihidropiridin-3-karbonitril molekülünün teorik olarak incelenmesi

Abstract

Bu çalışmada, 4-(metoksimetil)-1,6-dimetil-2-okso-1,2-dihidropiridin-3-karbonitril [C10H12N2O2] molekülünün geometrik parametreleri, harmonik titreşim dalga sayıları ve 1H and 13C nükleer magnetik rezonans (NMR) kimyasal kaymalarının kuantum kimyasal hesaplamaları temel seviyede HF ve DFT/B3LYP metodları kullanılarak hesaplandı. Optimize edilmiş moleküler yapıların sonuçları sunuldu ve deneysel değerler ile karşılaştırıldı. Gözlemlenen ve hesaplanan değerler arasında iyi bir uyum bulundu. Ek olarak, lineer olmayan optik (NLO) analizi, öncü moleküler bağ enerjisi, termodinamik parametreler, moleküler yüzeyler, Mulliken, APT ve NBO yükleri HF ve DFT kuantum kimyasal hesaplamaları kullanılarak incelendi.
Anahtar Kelimeler: 4-(metoksimetil)-1,6-dimetil-2-okso-1,2-dihidropiridin-3-karbonitril, HF ve DFT hesaplamaları, NLO analizi, moleküler yüzey (MEP ve ESP) haritaları.

Keywords

4-(metoksimetil)-1, 6-dimetil-2-okso-1, 2-dihidropiridin-3-karbonitril, HF ve DFT hesaplamaları, NLO analizi, moleküler yüzey (MEP ve ESP) haritaları.

References

• H. Thorn, Jr. Dunning, Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen, 1988.
• H. Pir Gümüş, Ö. Tamer, D. Avcı, Y. Atalay, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy , 2014, pp.183-190.
• M. Cetina, M. Tranfic, I. Sviben, M. Jukic; Synthesis, X-ray and spectroscopic analysis of some pyridine derivatives; Journal of Molecular Structure, 2010, pp. 25-32.
• GaussView, Version 5, Roy Dennington, Todd Keith and John Millam, Semichem Inc., Shawnee Mission KS, 2009.
• Gaussian 09, Revision A.1, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
• A. D. Becke, Density-functional exchange-energy approximation with correct asymptotic behavior, Physical Review A, 1988, pp. 3098-3100.
• C. Lee, W. Yang, R. G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B, 1998, pp. 785-789.
• J.P. Merrick, D. Moran, L. Radom, J Phys Chem A 2007, pp. 11683.
• K. Fukui, Role of Frontier Orbitals in Chemical Reactions, Science, 1982, pp. 747-754.
• R. S. Mulliken, J Chem Phys 1955, pp. 1833-1841.
• A. E. Reed, R. B. Weinstock, F. Weinhold, J Chem Phys 1985, pp. 735.
• A. E. Reed, F. Weinhold, J Chem Phys 1985, pp. 1736.
• A.E. Reed, L. A. Curtiss, F. Weinhold, Chem Rev 1988, pp. 899.
• ]P. Hohenberg and W. Kohn, Inhomogeneous electron gas, Phys. Rev. B, 1964, pp. 864-871.