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) |
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Pages (from-to) | 3351-3356 |
Number of pages | 6 |
Journal | European Journal of Organic Chemistry |
Issue number | 20 |
DOIs | |
State | Published - Jul 2009 |
Keywords
- Ab initio calculations /
- Hydrogen bonds /
- Lactones /
- Nmr spectroscopy
- Sialic acids /
ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry