Density functional study on the C-H bond cleavage of aldimine by a rhodium(I) catalyst

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

We investigated the C-H bond activation mechanism of aldimine by the [RhCl(PPH3)3] model catalyst using DFT B3LYP//SBKJC/6-31G*/6-31G on GAMESS. Due to their potential utility in organic synthesis, C-H bond activation is one of the most active research fields in organic and organometallic chemistry. C-H bond activation by a transition metal catalyst can be classified into two types of mechanisms: direct C-H bond cleavage by the metal catalyst or a multi-step mechanism via a tetrahedral transition state. There are three structural isomers of [RhCl(PH 3)2] coordinated aldimine that differ in the position of chloride with respect to the molecular plane. By comparing activation energies of the overall reaction pathways that the three isomeric structures follow in each mechanism, we found that the C-H bond activation of aldimine by the [RhCl(PH3)3] catalyst occurs through the tetrahedral intermediate.

Original languageEnglish
Pages (from-to)1920-1926
Number of pages7
JournalBulletin of the Korean Chemical Society
Volume29
Issue number10
DOIs
Publication statusPublished - 2008 Oct 20

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Rhodium
Chemical activation
Catalysts
Organometallics
Discrete Fourier transforms
Isomers
Transition metals
Chlorides
Activation energy
Metals

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

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title = "Density functional study on the C-H bond cleavage of aldimine by a rhodium(I) catalyst",
abstract = "We investigated the C-H bond activation mechanism of aldimine by the [RhCl(PPH3)3] model catalyst using DFT B3LYP//SBKJC/6-31G*/6-31G on GAMESS. Due to their potential utility in organic synthesis, C-H bond activation is one of the most active research fields in organic and organometallic chemistry. C-H bond activation by a transition metal catalyst can be classified into two types of mechanisms: direct C-H bond cleavage by the metal catalyst or a multi-step mechanism via a tetrahedral transition state. There are three structural isomers of [RhCl(PH 3)2] coordinated aldimine that differ in the position of chloride with respect to the molecular plane. By comparing activation energies of the overall reaction pathways that the three isomeric structures follow in each mechanism, we found that the C-H bond activation of aldimine by the [RhCl(PH3)3] catalyst occurs through the tetrahedral intermediate.",
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Density functional study on the C-H bond cleavage of aldimine by a rhodium(I) catalyst. / Yoo, Kyung-hwa; Jun, Chul-Ho; Cheol, Ho Choi; Sim, Eun Ji.

In: Bulletin of the Korean Chemical Society, Vol. 29, No. 10, 20.10.2008, p. 1920-1926.

Research output: Contribution to journalArticle

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T1 - Density functional study on the C-H bond cleavage of aldimine by a rhodium(I) catalyst

AU - Yoo, Kyung-hwa

AU - Jun, Chul-Ho

AU - Cheol, Ho Choi

AU - Sim, Eun Ji

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AB - We investigated the C-H bond activation mechanism of aldimine by the [RhCl(PPH3)3] model catalyst using DFT B3LYP//SBKJC/6-31G*/6-31G on GAMESS. Due to their potential utility in organic synthesis, C-H bond activation is one of the most active research fields in organic and organometallic chemistry. C-H bond activation by a transition metal catalyst can be classified into two types of mechanisms: direct C-H bond cleavage by the metal catalyst or a multi-step mechanism via a tetrahedral transition state. There are three structural isomers of [RhCl(PH 3)2] coordinated aldimine that differ in the position of chloride with respect to the molecular plane. By comparing activation energies of the overall reaction pathways that the three isomeric structures follow in each mechanism, we found that the C-H bond activation of aldimine by the [RhCl(PH3)3] catalyst occurs through the tetrahedral intermediate.

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