Modulating the preferred O—H...O hydrogen-bonding motif in a conformationally constrained environment through hydroxy-group derivatization

2010

Acta Cryst E

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The title compound, C18H25FO9, exhibits a similar unit cell and packing to the α polymorph of axial 4a,8a-dihydroxyperhydronaphthalene-2,3,6,7-tetrayl tetraacetate. The carbonyl O atoms of two of the four acetate groups in the molecule are disordered over two sites with occupancy ratios of 0.59 (4):0.41 (4) and 0.57 (6):0.43 (6). Crystal packing is effected via intermolecular O—H⋯O hydrogen bonds, which link the tetraacetate molecules into tapes along the c axis.

Section: Commentmentioning

confidence: 81%

Section: Commentmentioning

confidence: 99%

(2R,3R,4aS,6S,7S,8aS)-4a-Fluoro-8a-hydroxyperhydronaphthalene-2,3,6,7-tetrayl tetraacetate

Mehta

2010

Acta Cryst E

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“…2010, C66, o59 -Reproduced by permission of the International Union of Crystallography. [32] Scheme 2. Reagents and Conditions: [31] Elsevier] [31] Fig.…”

Section: Extending the Concept Of Conformational Locking To The Study...mentioning

confidence: 99%

“…Struct.Commun. 2010, C66, o59 -Reproduced by permission of the International Union of Crystallography [32].…”

mentioning

confidence: 99%

From Molecular to Supramolecular: An Exploration into the Modes of Self- assembly in Conformationally Locked Polycyclitols

Mehta¹,

2012

Chimia

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This brief account highlights the notable findings of our investigation into the supramolecular chemistry of conformationally locked polycyclitols in the solid state. The study was aimed at analyzing the crystal packing and unraveling the modalities of non-covalent interactions (particularly, intramolecular vis-à-vis intermolecular O-H˙˙˙O hydrogen bonds) in polyols. The know-how obtained thereof, was successfully utilized to engineer self-assemblies of designer polycyclitols, having hydrogen bond donors and acceptors fettered onto a trans-decalin scaffold. The results seek to draw particular attention to the intrinsic attribute of this rigid carbocyclic framework to lock functional groups into spatially invariant positions and bring potential intramolecular hydrogen bonding partners into favorable interaction geometry to engender predictability in the self-assembly patterns.

Probing Fluorine Interactions in a Polyhydroxylated Environment: Conservation of a C–F···H–C Recognition Motif in Presence of O–H···O Hydrogen Bonds

Mehta

2010

Eur J Org Chem

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Three conformationally locked fluorinated polycyclitols have been specially crafted on a rigid trans‐decalin backbone, employing a surprisingly facile pyridine‐poly(hydrogen fluoride)‐mediated stereospecific epoxide ring opening as the key reaction. Molecular design of the three fluorinated probes under study focused on providing an efficient platform for (a) evaluating the ability of covalently bonded fluorine, vis‐à‐vis the isosteric hydroxy group, to act as a H‐bond acceptor and (b) examining the possibility for an organic fluorine moiety, placed suitably in a spatially invariant position, to engage an 1,3‐diaxial OH functionality in a purported intramolecular O–H···F hydrogen bond. The present endeavour reveals that C(sp3)–F···H–C(sp3) hydrogen bonds, though weak and lesser investigated, can indeed be observed and supramolecular recognition motifs, involving such interactions, can be conserved even in crystal structures laden with stronger O–H···O hydrogen bonds.