Effect of ring in imines and enamines tautomerism in gas phase and solution: A computational study

• AZIN MOHAMADI ^[1] ; MEISAM SHABANIAN ^[1] ; MOHSEN HAJIBEYGI ^[1] ; HASSAN MOGHANIAN ^[1]
  1. [1] Islamic Azad University

     Islamic Azad University

     Irán

     
• Localización: Journal of the Chilean Chemical Society (Boletín de la Sociedad Chilena de Química), ISSN-e 0717-6309, ISSN 0366-1644, Vol. 58, Nº. 2, 2013, págs. 1659-1662
• Idioma: inglés
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• Resumen

  • Tautomeric structures from imine-enamine equilibria with rings of different size were geometrically optimized at the B3LYP/6-311++G** level of theory. Then important molecular parameters, IR frequencies, NBO and dipole moment results in the gas phase and solution were extracted. The energetic results show that relative stability of enamine tautomer (versus imine tautomer) increases with the increase of ring size and polarity of solvent. Calculated frequencies show the effect on the C=N frequency (imine tautomer) is attributed to ring size. The effect of increasing ring stain by decreasing ring size is to increase the C=N frequency. In addition, variation of dipole moments and NBO charges on atoms in the solvents are studied.