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Fine tuning the hydrophilic-hydrophobic balance in inositols through annulation: an analysis of the hydrogen-bonded architectures of 'annulated inositols'

Mehta, Goverdhan and Sen, Saikat (2005) Fine tuning the hydrophilic-hydrophobic balance in inositols through annulation: an analysis of the hydrogen-bonded architectures of 'annulated inositols'. In: CrystEngComm, 7 . pp. 656-663.

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Abstract

The crystal structures of conformationally locked, bicyclic cycloalkane-annulated variants of myo- and chiro-inositols have been analysed, in order to understand their mode of expression of the axial rich conformations and amphiphilicity in the solid state. Thus, while cyclohexa-annulated myo- and chiro-inositols exhibit a head-to-head bilayer molecular assembly, consisting of dimeric or octameric columnar architectures, cyclopenta-annulated chiro-inositol shows no such aggregation of the hydrophilic and hydrophobic faces, rather preferring to pack in a manner akin to a hydrophilic inositol. The differences in the two packing modes can be attributed to the size of the hydrocarbon ring, fine-tuning the hydrophilic-hydrophobic balance in the annulated inositols. An analysis of the non-polar molecular surface area (a measure of the intermolecular hydrophobic van der Waals interactions) for all the annulated inositols under study further vindicates the conclusion.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to Royal Society of Chemistry.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 27 Feb 2007
Last Modified: 27 Aug 2008 11:43
URI: http://eprints.iisc.ernet.in/id/eprint/5283

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