EFFECT OF RING IN IMINES AND ENAMINES TAUTOMERISM IN GAS PHASE AND SOLUTION: A COMPUTATIONAL STUDY
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 result...
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| Autores principales: | , , , |
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| Lenguaje: | English |
| Publicado: |
Sociedad Chilena de Química
2013
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| Materias: | |
| Acceso en línea: | http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000200003 |
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| Sumario: | 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. |
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