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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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 |
|---|---|
| Publication: | CrystEngComm |
| Publisher: | Royal Society of Chemistry |
| 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.ac.in/id/eprint/5283 |
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