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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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|
|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|
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