Theoretical study on the mechanism of N-heterocyclic carbene catalyzed transesterification reactions

Chun Liang Lai, Hon Man Lee, Ching Han Hu

Research output: Contribution to journalArticle

69 Citations (Scopus)

Abstract

The mechanism of N-heterocyclic carbene (NHC) catalyzed transesterification reactions have been studied using density functional theory. Our study shows that the role of NHC is to assist proton transfer from alcohol to the carbonyl oxygen, forming the tetrahedral intermediate, which then decomposes to the acylated product. Our predicted activation energies are in fine agreement with the observed reaction rates. An alternative approach, which uses the tetrahedral intermediate as the transition state mimic, provides satisfactory predictions.

Original languageEnglish (US)
Pages (from-to)6265-6270
Number of pages6
JournalTetrahedron Letters
Volume46
Issue number37
DOIs
StatePublished - Sep 12 2005
Externally publishedYes

Fingerprint

Transesterification
Theoretical Models
Proton transfer
Reaction rates
Density functional theory
Protons
Activation energy
Alcohols
Oxygen
carbene

Keywords

  • Density functional theory
  • NHC
  • Transesterification

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Theoretical study on the mechanism of N-heterocyclic carbene catalyzed transesterification reactions. / Lai, Chun Liang; Lee, Hon Man; Hu, Ching Han.

In: Tetrahedron Letters, Vol. 46, No. 37, 12.09.2005, p. 6265-6270.

Research output: Contribution to journalArticle

Lai, Chun Liang ; Lee, Hon Man ; Hu, Ching Han. / Theoretical study on the mechanism of N-heterocyclic carbene catalyzed transesterification reactions. In: Tetrahedron Letters. 2005 ; Vol. 46, No. 37. pp. 6265-6270.
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