Organic letters

Conformational preferences of a polar biaryl: a phase-and enantiomeric purity-dependent molecular hinge

J Clayden, SP Fletcher, SJM Rowbottom…

Index: Clayden, Jonathan; Fletcher, Stephen P.; McDouall, Joseph J. W.; Rowbottom, Stephen J. M. Journal of the American Chemical Society, 2009 , vol. 131, p. 5331 - 5343

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Citation Number: 9

Abstract

The favored (RS*, M*) diastereoisomer of 2-aryl-pyridine 1 in the solution state results from intramolecular dipole− dipole interactions. In the crystalline state, intermolecular interactions dominate, and the conformation switches reversibly to (RS*, P*). Only racemic 1 exhibits this switching property: enantiomerically pure 1 exists as the (RS*, M*) diastereoisomer in both the solution and crystalline state.