The observation of the C-H⋯Osp3 Hydrogen bond in trisialic acid lactone and its implications for cooperative lactonization

Chien Sheng Chen, Yi Ping Yu, Bo Chao Lin, Jacquelyn Gervay-Hague, Jim Min Fang, Chao Ping Hsu, Shih Hsiung Wu

Research output: Contribution to journalArticle

4 Scopus citations

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 9xO8, 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 languageEnglish (US)
Pages (from-to)3351-3356
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number20
DOIs
StatePublished - Jul 2009

Keywords

  • Ab initio calculations /
  • Hydrogen bonds /
  • Lactones /
  • Nmr spectroscopy
  • Sialic acids /

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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