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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 12, Number 2
BKCSDE 12(2)
February 20, 1991 

13C-NMR Study of the Applicaton of the “ Tools of Increasing Electron Demand ”to the 8-Aryl-tricyclo [,7]oct-8-yl Cations
Gweon-Young Ryu, Jung-Hyu Shin*
The 13C-NMR shifts of a series of para-substituted 8-aryl-tricyclo[,7]oct-8-yl and 9-aryl-tricyclo[,8]-non-9-yl cations were measured in FSO3H/SO2ClF at -90℃ in order to examine whether the ρC+ values can be used as a measure of the geometric influence on the charge delocalization resulting from σ conjugation in rigid tricyclopropylcarbinyl cations. Plot of the △δC+ shifts against the σC+ constants revealed excellent linear correlation. The 8-aryl tricyclooctyl systems yielded a ρC+ value of -5.00 with r = 0.9962. Previous investigation of the 9-aryl-tricyclononyl systems gave a correlation coefficient of r = 0.9948 with a slope of ρC+ = -4.95. A fair parallelism exists between the results of 19F-NMR studies and the change of ρC+ value in these cations. Consequently, it is established that the ρC+ value can be used to explain the mechanism of charge stabilization of the rigid cyclopropylcarbinyl cation such as tricyclo[,7]oct-8-yl cation.
193 - 196
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