The Observation of the C–H···O       sp       3       Hydrogen Bond in Trisialic Acid Lactone and Its Implications for Cooperative Lactonization | Zendy

Chen ChienSheng | Zendy; Yu YiPing | Zendy; Lin BoChao | Zendy; GervayHague Jacquelyn | Zendy; Fang JimMin | Zendy; Hsu ChaoPing | Zendy; Wu ShihHsiung | Zendy

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The Observation of the C–H···O sp 3 Hydrogen Bond in Trisialic Acid Lactone and Its Implications for Cooperative Lactonization

Author(s) -

Chen ChienSheng,

Yu YiPing,

Lin BoChao,

GervayHague Jacquelyn,

Fang JimMin,

Hsu ChaoPing,

Wu ShihHsiung

Publication year - 2009

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200900148

Subject(s) - chemistry , hydrogen bond , lactone , ab initio , stereochemistry , hydrogen , ab initio quantum chemistry methods , bond energy , catalysis , computational chemistry , crystallography , molecule , organic chemistry

The C–H ··· O sp 3hydrogen 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, 3 J correlations of B H 9 ax / A H 8 and C H 9 ax / B H 8 confirmed the existence of hydrogen‐bond connections of x +1 C 9 – x +1 H 9 ax ··· x O 8 . 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 sp 3stabilization in the lactone product. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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