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4-Substituted quinuclidinium perchlorates in the determination of polar substituent effects

✍ Scribed by E. Ceppi; W. Eckhardt; C.A. Grob


Publisher
Elsevier Science
Year
1973
Tongue
French
Weight
173 KB
Volume
14
Category
Article
ISSN
0040-4039

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✦ Synopsis


Reoeived in UK 10 July 1973; l coepted for publfoation 3 Augurt 1973)

determination of polar substituent constants by pK, measurements of corresponding salts has been recognized for some time 1) 2) 3) . Now that these compounds are more easily accessible 3) measurements can be carried out on a broader basis. The following Table lists the pKa values of the quinuclidinium perchlorates (I) measured to date in our laboratory 4) .


πŸ“œ SIMILAR VOLUMES


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## Abstract The rate constants for 3‐substituted adamantyl __p__‐toluenesulfonates **3a**‐**3k** in ethanol/water 80:20 correlate well with the respective inductive substituent constants Οƒ. The reaction constant ρ for the toluenesulfonates **3** is 10% larger than for the corresponding bromides **2

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## Abstract Thermodynamic p__K__~a~‐values have been determined for 38 4‐substituted quinuclidinium perchlorates. They are remarkably sensitive to the polar effect of the substituent and cover a range of 3.63 p__K__~a~ units. Furthermore, they vary linearly and almost equally with temperature since