TY - JOUR
T1 - Conformational preferences of a polar biaryl
T2 - A phase- and enantiomeric purity-dependent molecular hinge
AU - Clayden, Jonathan
AU - Fletcher, Stephen P.
AU - Rowbottom, S. J M
AU - Helliwell, Madeleine
PY - 2009/6/4
Y1 - 2009/6/4
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=66149161664&partnerID=8YFLogxK
U2 - 10.1021/ol9006635
DO - 10.1021/ol9006635
M3 - Article (Academic Journal)
C2 - 19435372
AN - SCOPUS:66149161664
SN - 1523-7060
VL - 11
SP - 2313
EP - 2316
JO - Organic Letters
JF - Organic Letters
IS - 11
ER -