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Conformational Analysis of N,N'-Phenylene-Diylbis[3-(1- Aminoethyl-6-Methyl-2H-Pyran-2,4(3H)-Dione]

Year 2018, Volume 5, Issue 2, 50 - 54, 28.12.2018

Abstract

Conformational analysis of N,N'-phenylenediylbis[3-(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione] were performed by using theoretical calculations. The possible stable conformers in keto-amine or imine-enol forms of N,N'-phenylenediylbis[3-(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione] on its potential energy surface (PES) were investigated by semi-empirical methods and hybrid-density functional theory (h-DFT) with the basis sets of different size and type. On account of relative energies and population analysis, the more stable forms of N,N'-phenylenediylbis[3-(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione were determined.

References

  • Gilli, P., Bertolasi, V., Ferretti, V. and Gilli, G., “Evidence for Intramolecular N−H•••O Resonance-Assisted Hydrogen Bonding in β-Enaminones and Related Heterodienes. A Combined Crystal-Structural, IR and NMR Spectroscopic, and Quantum-Mechanical Investigation”, J. Am. Chem. Soc., vol. 122, pp. 10405-10417, 2000.
  • Guo, Z.J., Faraglia G. and Sitran, S., “Palladium(II) and platinum(II) complexes with N-substituted methionines” Trans. Met. Chem., vol. 20, pp. 91-96, 1995.
  • Prakash, O., Kumar, A. and Singh S.P., “Synthesis of Heterocyclic Compounds from the Reactions of Dehydroacetic Acid (DHA) and Its Derivatives”, Heterocycles vol. 63, pp. 1193-908, 2004.
  • Luo, H., Liu, S., Rettig, S.R. and Orvig, C., “Rhenium and technetium complexes from pentadentate (N3O2) and tetradentate (N2O2) Schiff base ligands”, Can. J. Chem., vol 73, pp. 2272-2281, 1995.
  • Tan, S.-F., Ang, K.-P., Jayachandran, H.-L., Jones, A.J. and Berg, W.R., “1H, 13C, and 15N nuclear magnetic resonance studies on the tautomerism of the Schiff's bases of 3-acetyl-6-methyl-2H-pyran-2,4(3H)-dione and 3,5-diacetyltetrahydropyran-2,4,6-trione”, J. Chem. Soc., Perkin Trans., vol. 1, pp. 513-521, 1982.
  • Cindrić, M., Novak, T.K. and Užarević, K., “Molecular and crystal structures of N,N′-propylene- and N,N′-phenylene-diylbis [3-(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione]”, J. Mol. Struct., vol. 750, pp. 135-141, 2005.
  • Užarević, K., Rubčić, M., Stilinović, V., Kaitner, B., and Cindrić, M., “Keto–enol tautomerism in asymmetric Schiff bases derived from p-phenylenediamine”, J. Mol. Struct., vol. 984, pp. 232-239, 2010.
  • Mopac-PM3 and PM5 implemented in CAChe WorkSystem Pro. ver. 7.5.0 for Windows, Fujitsu Co. Ltd., Japan, 2006.
  • Frisch, M.J., et al, Gaussian 03 Revision D.01, Gaussian Inc., Wallingford CT, 2004.
  • Ünal, A., Şenyel, M. and Şentürk, Ş., “Conformational analysis and vibrational spectroscopic investigation of 3-phenylpropylamine”, Vib. Spectrosc., vol. 50, pp. 277-284, 2009.
  • Okur, M., Albayrak, N., Tamer, Ö., Avcı, D. and Atalay Y., “A theoretical study on N′-[(Z)-(4-Methylphenyl)Methylidene]-4-Nitrobenzohydrazide (NMPMN)”, Braz. J. Phys., vol. 48, pp. 398-405, 2018.
  • Ünal, A. and Okur, M., “Theoretical and experimental vibrational spectroscopy study on rotational isomer of 4-phenylbutylamine”, AIP. Conf. Proc.., vol. 1815, pp. 100006-1-100006-4, 2017.

Conformational Analysis of N,N'-Phenylene-Diylbis[3-(1-Aminoethyl-6-Methyl-2H-Pyran-2,4(3H)-Dione]

Year 2018, Volume 5, Issue 2, 50 - 54, 28.12.2018

Abstract

Conformational analysis of N,N'-phenylenediylbis[3-(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione] were performed by using theoretical calculations. The possible stable conformers in keto-amine or imine-enol forms of N,N'-phenylenediylbis[3-(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione] on its potential energy surface (PES) were investigated by semi-empirical methods and hybrid-density functional theory (h-DFT) with the basis sets of different size and type. On account of relative energies and population analysis, the more stable forms of N,N'-phenylenediylbis[3-(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione were determined.

References

  • Gilli, P., Bertolasi, V., Ferretti, V. and Gilli, G., “Evidence for Intramolecular N−H•••O Resonance-Assisted Hydrogen Bonding in β-Enaminones and Related Heterodienes. A Combined Crystal-Structural, IR and NMR Spectroscopic, and Quantum-Mechanical Investigation”, J. Am. Chem. Soc., vol. 122, pp. 10405-10417, 2000.
  • Guo, Z.J., Faraglia G. and Sitran, S., “Palladium(II) and platinum(II) complexes with N-substituted methionines” Trans. Met. Chem., vol. 20, pp. 91-96, 1995.
  • Prakash, O., Kumar, A. and Singh S.P., “Synthesis of Heterocyclic Compounds from the Reactions of Dehydroacetic Acid (DHA) and Its Derivatives”, Heterocycles vol. 63, pp. 1193-908, 2004.
  • Luo, H., Liu, S., Rettig, S.R. and Orvig, C., “Rhenium and technetium complexes from pentadentate (N3O2) and tetradentate (N2O2) Schiff base ligands”, Can. J. Chem., vol 73, pp. 2272-2281, 1995.
  • Tan, S.-F., Ang, K.-P., Jayachandran, H.-L., Jones, A.J. and Berg, W.R., “1H, 13C, and 15N nuclear magnetic resonance studies on the tautomerism of the Schiff's bases of 3-acetyl-6-methyl-2H-pyran-2,4(3H)-dione and 3,5-diacetyltetrahydropyran-2,4,6-trione”, J. Chem. Soc., Perkin Trans., vol. 1, pp. 513-521, 1982.
  • Cindrić, M., Novak, T.K. and Užarević, K., “Molecular and crystal structures of N,N′-propylene- and N,N′-phenylene-diylbis [3-(1-aminoethyl)-6-methyl-2H-pyran-2,4(3H)-dione]”, J. Mol. Struct., vol. 750, pp. 135-141, 2005.
  • Užarević, K., Rubčić, M., Stilinović, V., Kaitner, B., and Cindrić, M., “Keto–enol tautomerism in asymmetric Schiff bases derived from p-phenylenediamine”, J. Mol. Struct., vol. 984, pp. 232-239, 2010.
  • Mopac-PM3 and PM5 implemented in CAChe WorkSystem Pro. ver. 7.5.0 for Windows, Fujitsu Co. Ltd., Japan, 2006.
  • Frisch, M.J., et al, Gaussian 03 Revision D.01, Gaussian Inc., Wallingford CT, 2004.
  • Ünal, A., Şenyel, M. and Şentürk, Ş., “Conformational analysis and vibrational spectroscopic investigation of 3-phenylpropylamine”, Vib. Spectrosc., vol. 50, pp. 277-284, 2009.
  • Okur, M., Albayrak, N., Tamer, Ö., Avcı, D. and Atalay Y., “A theoretical study on N′-[(Z)-(4-Methylphenyl)Methylidene]-4-Nitrobenzohydrazide (NMPMN)”, Braz. J. Phys., vol. 48, pp. 398-405, 2018.
  • Ünal, A. and Okur, M., “Theoretical and experimental vibrational spectroscopy study on rotational isomer of 4-phenylbutylamine”, AIP. Conf. Proc.., vol. 1815, pp. 100006-1-100006-4, 2017.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Arslan ÜNAL> (Primary Author)
BILECIK SEYH EDEBALI UNIVERSITY
0000-0002-5857-7318
Türkiye


Muhammet OKUR This is me
BILECIK SEYH EDEBALI UNIVERSITY
0000-0002-1114-1349
Türkiye

Publication Date December 28, 2018
Application Date November 21, 2018
Acceptance Date December 3, 2018
Published in Issue Year 2018, Volume 5, Issue 2

Cite

APA Ünal, A. & Okur, M. (2018). Conformational Analysis of N,N'-Phenylene-Diylbis[3-(1- Aminoethyl-6-Methyl-2H-Pyran-2,4(3H)-Dione] . Bilecik Şeyh Edebali Üniversitesi Fen Bilimleri Dergisi , 5 (2) , 50-54 . Retrieved from https://dergipark.org.tr/en/pub/bseufbd/issue/41708/486208