Barriers to rotation in a range up to 15.4 kcal mol-1 were determined by dynamic NMR spectroscopy for a series of biphenyl compounds 1a-1h and 2a -2d with a single ortho-substituent. Ab initio calculations reproduce these barriers satisfactorily and indicate the ground-state conformation of these molecules. Results are discussed in terms of the contribution of individual substituents to the barrier and of the buttressing of adjacent positions in a benzene ring by substituents.
A.Mazzanti, L. Lunazzi, M. Minzoni, J. E. Anderson (2006). Rotation in Biphenyls with a Single ortho-Substituent. JOURNAL OF ORGANIC CHEMISTRY, 71, 5474-5481 [10.1021/jo060205b].
Rotation in Biphenyls with a Single ortho-Substituent
MAZZANTI, ANDREA;LUNAZZI, LODOVICO;MINZONI, MIRKO;
2006
Abstract
Barriers to rotation in a range up to 15.4 kcal mol-1 were determined by dynamic NMR spectroscopy for a series of biphenyl compounds 1a-1h and 2a -2d with a single ortho-substituent. Ab initio calculations reproduce these barriers satisfactorily and indicate the ground-state conformation of these molecules. Results are discussed in terms of the contribution of individual substituents to the barrier and of the buttressing of adjacent positions in a benzene ring by substituents.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
