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Polar Effects. Part 14. Inductive Charge Dispersal in Bicyclo[2.2.2]oct-1-yl Cations

✍ Scribed by Rolf Bielmann; Cyril A. Grob; Dieter Küry; Guo Wei Yao

Publisher
John Wiley and Sons
Year
1985
Tongue
German
Weight
330 KB
Volume
68
Category
Article
ISSN
0018-019X

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✦ Synopsis

Standard deviations of the pK,, upon which n? values are based, and of the conductometric rate measurements, as well uncertainties regarding the orientation of dipolar substituents, contribute to this limitation, as in most Hammett treatments. The I3C-NMR signals for the a-, /3-, and r-C-atoms in the quinuclidinium ion in CF,COOH were reported as 48. 10,22.90, and 19.30, respectively [19].

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The pKa of 2-, 3-and 4-substituted quinuclidinium perchlorates and the solvolysis rates of the corresponding bicyclo[2.2.2loctyl-l-pnitrobenzenesulfonates reveal the dispersal of charge in ammonium ions and carbocations. Recent studies1 have shown that the solvolysis rates (log k) of several substi

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Inductivity was defined as thc reaction constant p, in the equation log (klk,) = pluq, where k and k, are fmt-order rate consmiits for the substitutcd and unsubstituted tosylates, respectively, in 80% EtOH and u? i s the corresponding inductive substituent constant [3]. For recent reviews, see [2].