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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Energy barriers to rotation in axially chiral analogues of 4-(dimethylamino)pyridine.

The barriers to enantiomerization of a series of axially chiral biaryl analogues of 4-(dimethylamino)pyridine (DMAP) 1-10 were determined experimentally by means of dynamic HPLC measurements and racemization studies. The barriers to rotation in derivatives 1-6 (based on the bicyclic 5-azaindoline core) were lower than those in the corresponding derivatives 7-10 (based on the monocyclic DMAP core). Semiempirical (PM3), ab initio Hartree-Fock (HF/STO-3G), and density functional theory (DFT/B3LYP/6-31G*) calculations reveal that these differences in barriers to rotation are the result of differing degrees of hybridization of the non-pyridyl nitrogen in the enantiomerization transition states (TSs). The importance of heteroatom hybridization as a factor in determining nonsteric contributions to barriers to rotation in azabiaryls of this type is discussed.[1]


  1. Energy barriers to rotation in axially chiral analogues of 4-(dimethylamino)pyridine. Spivey, A.C., Charbonneau, P., Fekner, T., Hochmuth, D.H., Maddaford, A., Malardier-Jugroot, C., Redgrave, A.J., Whitehead, M.A. J. Org. Chem. (2001) [Pubmed]
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