STRUCTURES OF CHARGE-PERTURBED OR STERICALLY OVERCROWDED MOLECULES .29. STERIC OVERCROWDING IN N-TRIMETHYLSILYL-SUBSTITUTED-P-PHENYLENEDIAMINES - THE ORIGIN OF A WURSTERS BLUE RADICAL-ANION
H. Bock et al., STRUCTURES OF CHARGE-PERTURBED OR STERICALLY OVERCROWDED MOLECULES .29. STERIC OVERCROWDING IN N-TRIMETHYLSILYL-SUBSTITUTED-P-PHENYLENEDIAMINES - THE ORIGIN OF A WURSTERS BLUE RADICAL-ANION, Tetrahedron letters, 34(47), 1993, pp. 7553-7556
The crystal structure of N,N'-bis(trimethylsilyl)-p-phenylene diamine
proves an almost planar, though heavily distorted SiHN-C6H4-NHSi skele
ton, whereas in the sterically overcrowded N,N,N',N'-tetrakis(trimethy
lsilyl) derivative the p-type electron pairs of the flattened (R3Si)2N
groups are twisted into the plane of the benzene ring and, therefore,
provide a rationale for its unexpectedly possible one-electron reduct
ion to a Wurster's Blue radical anion.