TY - JOUR
T1 - Conformational communication between the Ar-CO and Ar-N axes in 2,2′-disubstituted benzanilides and their derivatives
AU - Clayden, Jonathan
AU - Vallverdú, Lluís
AU - Helliwell, Madeleine
PY - 2006/6/7
Y1 - 2006/6/7
N2 - Benzanilides containing two or more potentially stereogenic amide axes exist in solution as mixtures of conformers which are detectable by NMR. For simple tertiary benzanilides carrying an ortho substituent on each ring, conformational control can be high (up to about 10: 1) providing the substituents are large, indicating that the two axes are in conformational communication with one another. For more complex diamides, conformational communication breaks down, and mixtures of conformers are evident by NMR.
AB - Benzanilides containing two or more potentially stereogenic amide axes exist in solution as mixtures of conformers which are detectable by NMR. For simple tertiary benzanilides carrying an ortho substituent on each ring, conformational control can be high (up to about 10: 1) providing the substituents are large, indicating that the two axes are in conformational communication with one another. For more complex diamides, conformational communication breaks down, and mixtures of conformers are evident by NMR.
UR - http://www.scopus.com/inward/record.url?scp=33744785161&partnerID=8YFLogxK
U2 - 10.1039/b602912d
DO - 10.1039/b602912d
M3 - Article (Academic Journal)
AN - SCOPUS:33744785161
SN - 1477-0520
VL - 4
SP - 2106
EP - 2118
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 11
ER -