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

Jonathan Clayden*, Stephen P. Fletcher, S. J M Rowbottom, Madeleine Helliwell

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

10 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2313-2316
Number of pages4
JournalOrganic Letters
Volume11
Issue number11
Early online date12 May 2009
DOIs
Publication statusPublished - 4 Jun 2009

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