DFT STUDY ON THE MECHANISM OF THE ADDITION REACTION BETWEEN CARBENE AND GLYCINE

The mechanism of addition reaction between the singlet carbene and glycine has been investigated at the B3LYP/6-311+G* level of theory, including geometry optimization and vibrational analysis for the involved stationary points on the potential energy surface. Computational results suggest that ther...

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Autores principales:	TAN,XIAOJUN, WANG,WEIHUA, LI,PING, GU,JINSONG, WANG,GUORONG, WANG,DANGSHENG, LI,TAO
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2011
Materias:	Carbene Glycine Addition reaction Density functional theory (DFT)
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072011000100024
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spelling	oai:scielo:S0717-970720110001000242011-06-17DFT STUDY ON THE MECHANISM OF THE ADDITION REACTION BETWEEN CARBENE AND GLYCINETAN,XIAOJUNWANG,WEIHUALI,PINGGU,JINSONGWANG,GUORONGWANG,DANGSHENGLI,TAO Carbene Glycine Addition reaction Density functional theory (DFT) The mechanism of addition reaction between the singlet carbene and glycine has been investigated at the B3LYP/6-311+G* level of theory, including geometry optimization and vibrational analysis for the involved stationary points on the potential energy surface. Computational results suggest that there are two reaction pathways (1) and (2) during the addition process. In the pathway (1), carbene attacks the C=O bond from the H¹C¹C² side of glycine to form an intermediate (IM1), which is a barrier-free exothermic reaction. Then, IM1 isomerizes to a product (Pro1) via a transition state (TS1) with a potential barrier of 25.7 kJ/mol. Similarly, in the pathway (2), carbene attacks the C=O bond from the H²C¹C² side of glycine to form an intermediate IM2. Subsequently, IM2 isomerizes to Pro2 via TS2, where the Pro2 and Pro1 are enantiomers actually. The calculated potential barrier of 51.3 kJ/mol is higher than that of the pathway (1). Correspondingly, the reaction energy for the both pathways is -258.5 kJ/mol. Additionally, the atoms in molecules (AIM) theory has also been performed to characterize the bonding interaction and structural features for the addition reaction.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.56 n.1 20112011-01-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072011000100024en10.4067/S0717-97072011000100024
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	Carbene Glycine Addition reaction Density functional theory (DFT)
spellingShingle	Carbene Glycine Addition reaction Density functional theory (DFT) TAN,XIAOJUN WANG,WEIHUA LI,PING GU,JINSONG WANG,GUORONG WANG,DANGSHENG LI,TAO DFT STUDY ON THE MECHANISM OF THE ADDITION REACTION BETWEEN CARBENE AND GLYCINE
description	The mechanism of addition reaction between the singlet carbene and glycine has been investigated at the B3LYP/6-311+G* level of theory, including geometry optimization and vibrational analysis for the involved stationary points on the potential energy surface. Computational results suggest that there are two reaction pathways (1) and (2) during the addition process. In the pathway (1), carbene attacks the C=O bond from the H¹C¹C² side of glycine to form an intermediate (IM1), which is a barrier-free exothermic reaction. Then, IM1 isomerizes to a product (Pro1) via a transition state (TS1) with a potential barrier of 25.7 kJ/mol. Similarly, in the pathway (2), carbene attacks the C=O bond from the H²C¹C² side of glycine to form an intermediate IM2. Subsequently, IM2 isomerizes to Pro2 via TS2, where the Pro2 and Pro1 are enantiomers actually. The calculated potential barrier of 51.3 kJ/mol is higher than that of the pathway (1). Correspondingly, the reaction energy for the both pathways is -258.5 kJ/mol. Additionally, the atoms in molecules (AIM) theory has also been performed to characterize the bonding interaction and structural features for the addition reaction.
author	TAN,XIAOJUN WANG,WEIHUA LI,PING GU,JINSONG WANG,GUORONG WANG,DANGSHENG LI,TAO
author_facet	TAN,XIAOJUN WANG,WEIHUA LI,PING GU,JINSONG WANG,GUORONG WANG,DANGSHENG LI,TAO
author_sort	TAN,XIAOJUN
title	DFT STUDY ON THE MECHANISM OF THE ADDITION REACTION BETWEEN CARBENE AND GLYCINE
title_short	DFT STUDY ON THE MECHANISM OF THE ADDITION REACTION BETWEEN CARBENE AND GLYCINE
title_full	DFT STUDY ON THE MECHANISM OF THE ADDITION REACTION BETWEEN CARBENE AND GLYCINE
title_fullStr	DFT STUDY ON THE MECHANISM OF THE ADDITION REACTION BETWEEN CARBENE AND GLYCINE
title_full_unstemmed	DFT STUDY ON THE MECHANISM OF THE ADDITION REACTION BETWEEN CARBENE AND GLYCINE
title_sort	dft study on the mechanism of the addition reaction between carbene and glycine
publisher	Sociedad Chilena de Química
publishDate	2011
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072011000100024
work_keys_str_mv	AT tanxiaojun dftstudyonthemechanismoftheadditionreactionbetweencarbeneandglycine AT wangweihua dftstudyonthemechanismoftheadditionreactionbetweencarbeneandglycine AT liping dftstudyonthemechanismoftheadditionreactionbetweencarbeneandglycine AT gujinsong dftstudyonthemechanismoftheadditionreactionbetweencarbeneandglycine AT wangguorong dftstudyonthemechanismoftheadditionreactionbetweencarbeneandglycine AT wangdangsheng dftstudyonthemechanismoftheadditionreactionbetweencarbeneandglycine AT litao dftstudyonthemechanismoftheadditionreactionbetweencarbeneandglycine
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DFT STUDY ON THE MECHANISM OF THE ADDITION REACTION BETWEEN CARBENE AND GLYCINE

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