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

Arslan Ünal , Muhammet Okur

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.

Keywords

Conformational analysis, DFT, PES, N.N'-phenylenediylbis, 3-(1-aminoethyl)-6-methyl-2H-pyran-2.4(3H)-dione, , Tautomerism

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

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.

Keywords

Conformational analysis, DFT, PES, N.N'-phenylenediylbis3-(1-aminoethyl)-6-methyl-2H-pyran-2.4(3H)-dione, Tautomerism

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.