Tryst with a molecular and supramolecular oddity: an anti-Furst-Plattner epoxide opening product as a designer additive for accessing an elusive polymorph

Mehta, Goverdhan and Sen, Saikat (2009) Tryst with a molecular and supramolecular oddity: an anti-Furst-Plattner epoxide opening product as a designer additive for accessing an elusive polymorph. In: Tetrahedron, 65 (47). pp. 9713-9718.

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Abstract

Additive induced polymorphism of a conformationally locked tetraacetate 3 in presence of its diastereomer 4 is described. The ester 3 was specially crafted on a trans-decalin backbone to relegate the O-H center dot center dot center dot O H-bond donors to the molecular interior and have the peripheral H-bond acceptors in 1,3-syndiaxial relationship. The supramolecular assembly of 3 was destined to evolve along two mutually exclusive pathways, namely one, which employs intermolecular O-H center dot center dot center dot O H-bonds (pathway 1) and the other that sacrifices these for intramolecular O-H center dot center dot center dot O H-bonds and settles for a crystal packing dictated by weak intermolecular interactions alone (pathway 2). Exploiting the similarity between the self-assemblies of 4 and the two recently reported dimorphs of 3, the ester 3 has been stimulated to follow the elusive non-hierarchical pathway 2 through preferential inhibition of pathway 1. Interestingly, the inhibitor 4 was obtained serendipitously en route 3 via an apparent breakdown of Furst-Plattner rule.

Item Type:	Journal Article
Publication:	Tetrahedron
Publisher:	Elsevier Science
Additional Information:	Copyright for this article belongs to Elsevier Science.
Keywords:	Crystal engineering; Hydrolysis; Hydrogen bonds; Polycyclitols; Polymorphism
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	03 Dec 2009 10:06
Last Modified:	19 Sep 2010 05:53
URI:	http://eprints.iisc.ac.in/id/eprint/25045

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