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

doi:10.1002/ejoc.200900148

The observation of the C-H⋯O^sp3 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

Chemistry

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

The C-H⋯O^sp3 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 ^BH_ax ⁹/^AH⁸ and ^CH_ax/^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	https://doi.org/10.1002/ejoc.200900148
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

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The observation of the C-H⋯O^sp3 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 › peer-review

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

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.",

keywords = "Ab initio calculations /, Hydrogen bonds /, Lactones /, Nmr spectroscopy, Sialic acids /",

author = "Chen, {Chien Sheng} and Yu, {Yi Ping} and Lin, {Bo Chao} and Jacquelyn Gervay-Hague and Fang, {Jim Min} and Hsu, {Chao Ping} and Wu, {Shih Hsiung}",

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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

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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 /

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