Mehta, Goverdhan ; Sen, Saikat (2010) Probing fluorine interactions in a polyhydroxylated environment: conservation of a C-F···H-C recognition motif in presence of O-H···O hydrogen bonds European Journal of Organic Chemistry, 2010 (18). pp. 3387-3394. ISSN 1434-193X
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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.20...
Related URL: http://dx.doi.org/10.1002/ejoc.201000226
Abstract
Three conformationally locked fluorinated polycyclitols have been specially crafted on a rigid trans-decalin backbone, employing a surprisingly facile pyridine-poly(hydrogen fluoride)-mediated stereospecific epoxide ring opening as the key reaction. Molecular design of the three fluorinated probes under study focused on providing an efficient platform for (a) evaluating the ability of covalently bonded fluorine, vis-a-vis the isosteric hydroxy group, to act as a H-bond acceptor and (b) examining the possibility for an organic fluorine moiety, placed suitably in a spatially invariant position, to engage an 1,3-diaxial OH functionality in a purported intramolecular O-H···F hydrogen bond. The present endeavour reveals that C(sp3)-F···H-C(sp3) hydrogen bonds, though weak and lesser investigated, can indeed be observed and supramolecular recognition motifs, involving such interactions, can be conserved even in crystal structures laden with stronger O-H…O hydrogen bonds.
Item Type: | Article |
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Source: | Copyright of this article belongs to John Wiley and Sons, Inc. |
Keywords: | Alcohols; Alicyclic Compounds; Fluorine; Hydrogen Bonds; Non-covalent Interactions |
ID Code: | 29296 |
Deposited On: | 17 Dec 2010 08:15 |
Last Modified: | 17 Dec 2010 08:15 |
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