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Issue 5, 2008
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Understanding the self-assembling process in crystalline cyclooctitols: an insight into the conformational flexibility of medium-sized rings

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Abstract

The crystal structures of two closely related cyclooctitols 1 and 2, in the form of their acetonide derivatives, have been analysed, in order to investigate the interrelationship between the preferred mode of self-assembly and conformation of the eight-membered carbocyclic ring in the solid state. While dissimilar in their conformation, the diols 1 and 2 exhibit remarkable similarity in their molecular packing which appear to define an interesting motif in the form of repeating figures of “8”, with the polar hydroxyl groups forming the interior “links” and the lipophilic molecular bulk the exterior “bends”. Observed differences in the conformation of the cyclooctane ring in crystalline 1 and 2vis-à-vis that deduced on the basis of energy minimization could be related to an interplay in the degree of pliancy of the eight-membered ring and conformation-directing ability of competing inter- and intramolecular hydrogen bonds.

Graphical abstract: Understanding the self-assembling process in crystalline cyclooctitols: an insight into the conformational flexibility of medium-sized rings

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Publication details

The article was received on 21 Aug 2007, accepted on 03 Dec 2007, published on 10 Jan 2008 and first published online on 10 Jan 2008


Article type: Paper
DOI: 10.1039/B712877K
Citation: CrystEngComm, 2008,10, 534-540
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    Understanding the self-assembling process in crystalline cyclooctitols: an insight into the conformational flexibility of medium-sized rings

    G. Mehta, S. Sen and K. Pallavi, CrystEngComm, 2008, 10, 534
    DOI: 10.1039/B712877K

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