39869-70-0Relevant articles and documents
The Octant Rule. 7. Deuterium as an Octant Pertuber
Lightner, David A.,Gawronski, Jacek K.,Bouman, Thomas D.
, p. 1983 - 1990 (2007/10/02)
(1S)-exo-2-Deuteriobicycloheptan-7-one (1) and (1S)-endo-2-deuteriobicycloheptan-7-one (2) were synthesized, and their circular dichroism spectra were measured and analyzed.Both ketones show dissignate Cotton effects near 295 nm corresponding to their n-?* electronic transitions: 1 (Δε296 = +0.033) and 2 (Δε292 = +0.132).The nature of the isotopic perturbation on the n-?* transitions of 1 and 2, related β-deuterioadamantanones and cyclohexanones, and α-deuteriocyclohexanones is treated theoretically.The net contribution to the sign of the rotatory strength is determined by the relatively more consignate contribution on the C-H bond that is located in an oppositely signed octant relative to the C-D bond.