Strength from weakness: opportunistic CH⋯O hydrogen bonds differentially dictate the conformational fate in solid and solution states

Vibhute, Amol M. ; Gonnade, Rajesh G. ; Swathi, R. S. ; Sureshan, Kana M. (2012) Strength from weakness: opportunistic CH⋯O hydrogen bonds differentially dictate the conformational fate in solid and solution states Chemical Communications, 48 (5). pp. 717-719. ISSN 1359-7345

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Official URL: http://doi.org/10.1039/C1CC15051K

Related URL: http://dx.doi.org/10.1039/C1CC15051K

Abstract

We show that the CH⋯O hydrogen bond can be opportunistic to differentially dictate the conformation of cyclitols in solution and solid states. While several intermolecular CH⋯O stabilize the chair-conformation in the solid, single intramolecular CH⋯O stabilizes an otherwise unfavorable boat-conformation in solutions analogous to the boat-conformation of cis-1,4-cyclohexanediols by OH⋯O bonds.

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