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:	MOHAMADI,AZIN, SHABANIAN,MEISAM, HAJIBEYGI,MOHSEN, MOGHANIAN,HASSAN
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2013
Materias:	DFT study NBO analysis PC model imine enamine
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000200003
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spelling	oai:scielo:S0717-970720130002000032014-09-09EFFECT OF RING IN IMINES AND ENAMINES TAUTOMERISM IN GAS PHASE AND SOLUTION: A COMPUTATIONAL STUDYMOHAMADI,AZINSHABANIAN,MEISAMHAJIBEYGI,MOHSENMOGHANIAN,HASSAN DFT study NBO analysis PC model imine enamine 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.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.58 n.2 20132013-01-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000200003en10.4067/S0717-97072013000200003
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	DFT study NBO analysis PC model imine enamine
spellingShingle	DFT study NBO analysis PC model imine enamine MOHAMADI,AZIN SHABANIAN,MEISAM HAJIBEYGI,MOHSEN MOGHANIAN,HASSAN EFFECT OF RING IN IMINES AND ENAMINES TAUTOMERISM IN GAS PHASE AND SOLUTION: A COMPUTATIONAL STUDY
description	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.
author	MOHAMADI,AZIN SHABANIAN,MEISAM HAJIBEYGI,MOHSEN MOGHANIAN,HASSAN
author_facet	MOHAMADI,AZIN SHABANIAN,MEISAM HAJIBEYGI,MOHSEN MOGHANIAN,HASSAN
author_sort	MOHAMADI,AZIN
title	EFFECT OF RING IN IMINES AND ENAMINES TAUTOMERISM IN GAS PHASE AND SOLUTION: A COMPUTATIONAL STUDY
title_short	EFFECT OF RING IN IMINES AND ENAMINES TAUTOMERISM IN GAS PHASE AND SOLUTION: A COMPUTATIONAL STUDY
title_full	EFFECT OF RING IN IMINES AND ENAMINES TAUTOMERISM IN GAS PHASE AND SOLUTION: A COMPUTATIONAL STUDY
title_fullStr	EFFECT OF RING IN IMINES AND ENAMINES TAUTOMERISM IN GAS PHASE AND SOLUTION: A COMPUTATIONAL STUDY
title_full_unstemmed	EFFECT OF RING IN IMINES AND ENAMINES TAUTOMERISM IN GAS PHASE AND SOLUTION: A COMPUTATIONAL STUDY
title_sort	effect of ring in imines and enamines tautomerism in gas phase and solution: a computational study
publisher	Sociedad Chilena de Química
publishDate	2013
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000200003
work_keys_str_mv	AT mohamadiazin effectofringiniminesandenaminestautomerismingasphaseandsolutionacomputationalstudy AT shabanianmeisam effectofringiniminesandenaminestautomerismingasphaseandsolutionacomputationalstudy AT hajibeygimohsen effectofringiniminesandenaminestautomerismingasphaseandsolutionacomputationalstudy AT moghanianhassan effectofringiniminesandenaminestautomerismingasphaseandsolutionacomputationalstudy
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EFFECT OF RING IN IMINES AND ENAMINES TAUTOMERISM IN GAS PHASE AND SOLUTION: A COMPUTATIONAL STUDY

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