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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 17, Number 4
BKCSDE 17(4)
April 20, 1996 

A New Substituent Constant, σc+s ; a Fit for π-Participation in Modified Hammett-Brown Equation
Jung Ho Cho, Jung-Hyu Shin*
A set of substituent constants, σc+, has been widely used comparing the stability of carbocation in super acid condition. Plotting of 13C chemical shifts of cationic carbon (Δδc+) against σc+ constants yields an excellent correlation with a good correlation coefficient (r=0.999) for a cyclopentyl cation system. But these σc+ constants show poor linearity in norbornenyl cations that well known to show homoallylic stabilization in a cationic condition. We calculated the new substituent constant, σc+π, and found that the new substituent constants give an excellent correlation in π- and πσ -participating cation systems.
347 - 348
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