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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 10, Number 6
BKCSDE 10(6)
June 20, 1989 

13C NMR Study of the Application of the
Wie-Chang Jin, Gweon-Young Ryu, Chun Yoon, Jung Hyu Shin*
The13C NMR shifts of a series of para-substituted 9-aryl-tricyclo[,8]non-9-yl and 8-aryl-tetracyclo[,7.04,6]-oct-8-yl cations were measured in FSO3H/SO2ClF at -90℃ or -70℃ in order to examine whether the ρc+ values can be used to explain the mechanism for the stabilization of the geometrically rigid cyclopropylcarbinyl cations. Plots of the Δδc+ shifts against σc+ reveal excellent linear correlation. The tricyclononyl systems yield a ρ c+ value of -4.95 with a correlation coefficient r = 0.9948. The tetracyclo-octanyl systems give a ρ c+ value of -6.39 with r = 0.9943. A fair parallelism exists between the results of 19F nmr studies and the change of ρc+ values in these cations. Accordingly, the present study established that the ρc+ value can be used as a mearsure of the geometric influence for the charge delocalization in cyclopropylcarbinyl cations.
591 - 595
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