Abstract
The C-H⋯Osp3 hydrogen bond in trisialic acid, lactones has been examined by using long-range COSY (LRCOSY) and ab initio calculations, From an analysis of the LRCOSY spectra, 3J correlations of BHax 9/AH8 and CHax/BH8 confirmed the existence of hydrogen-bond connections of X+1C9-X+1H ax 9⋯ xO8, The theoretical, bond energy of the hydrogen bond was estimated to be 1.0 or 1.6 kcal/mol by using two models. The acid-catalyzed cooperative lactonization of Oligosialic acids can be understood in terms of the additional C-H⋯O sp3 stabilization in the lactone product.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 3351-3356 |
| Number of pages | 6 |
| Journal | European Journal of Organic Chemistry |
| Issue number | 20 |
| DOIs | |
| State | Published - Jul 2009 |
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Keywords
- Ab initio calculations /
- Hydrogen bonds /
- Lactones /
- Nmr spectroscopy
- Sialic acids /
ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
Cite this
The observation of the C-H⋯Osp3 Hydrogen bond in trisialic acid lactone and its implications for cooperative lactonization. / Chen, Chien Sheng; Yu, Yi Ping; Lin, Bo Chao; Gervay-Hague, Jacquelyn; Fang, Jim Min; Hsu, Chao Ping; Wu, Shih Hsiung.
In: European Journal of Organic Chemistry, No. 20, 07.2009, p. 3351-3356.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - The observation of the C-H⋯Osp3 Hydrogen bond in trisialic acid lactone and its implications for cooperative lactonization
AU - Chen, Chien Sheng
AU - Yu, Yi Ping
AU - Lin, Bo Chao
AU - Gervay-Hague, Jacquelyn
AU - Fang, Jim Min
AU - Hsu, Chao Ping
AU - Wu, Shih Hsiung
PY - 2009/7
Y1 - 2009/7
N2 - The C-H⋯Osp3 hydrogen bond in trisialic acid, lactones has been examined by using long-range COSY (LRCOSY) and ab initio calculations, From an analysis of the LRCOSY spectra, 3J correlations of BHax 9/AH8 and CHax/BH8 confirmed the existence of hydrogen-bond connections of X+1C9-X+1H ax 9⋯ xO8, The theoretical, bond energy of the hydrogen bond was estimated to be 1.0 or 1.6 kcal/mol by using two models. The acid-catalyzed cooperative lactonization of Oligosialic acids can be understood in terms of the additional C-H⋯O sp3 stabilization in the lactone product.
AB - The C-H⋯Osp3 hydrogen bond in trisialic acid, lactones has been examined by using long-range COSY (LRCOSY) and ab initio calculations, From an analysis of the LRCOSY spectra, 3J correlations of BHax 9/AH8 and CHax/BH8 confirmed the existence of hydrogen-bond connections of X+1C9-X+1H ax 9⋯ xO8, The theoretical, bond energy of the hydrogen bond was estimated to be 1.0 or 1.6 kcal/mol by using two models. The acid-catalyzed cooperative lactonization of Oligosialic acids can be understood in terms of the additional C-H⋯O sp3 stabilization in the lactone product.
KW - Ab initio calculations /
KW - Hydrogen bonds /
KW - Lactones /
KW - Nmr spectroscopy
KW - Sialic acids /
UR - http://www.scopus.com/inward/record.url?scp=67650500791&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=67650500791&partnerID=8YFLogxK
U2 - 10.1002/ejoc.200900148
DO - 10.1002/ejoc.200900148
M3 - Article
AN - SCOPUS:67650500791
SP - 3351
EP - 3356
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 20
ER -