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 language | English |
|---|---|
| Pages (from-to) | 6265-6270 |
| Number of pages | 6 |
| Journal | Tetrahedron Letters |
| Volume | 46 |
| Issue number | 37 |
| DOIs | |
| Publication status | Published - 2005 Sep 12 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
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}
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 journal › Article
TY - JOUR
T1 - Theoretical study on the mechanism of N-heterocyclic carbene catalyzed transesterification reactions
AU - Lai, Chun Liang
AU - Lee, Hon Man
AU - Hu, Ching Han
PY - 2005/9/12
Y1 - 2005/9/12
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=23744504555&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=23744504555&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2005.07.046
DO - 10.1016/j.tetlet.2005.07.046
M3 - Article
AN - SCOPUS:23744504555
VL - 46
SP - 6265
EP - 6270
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 37
ER -