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Inductivity and charge dispersal in quinuclidinium and bicyclo[2.2.2]octyl-1-cations

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

Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
212 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 substituted bi-and tricyclic arylsulfonates correlate well with inductive substituent constants 62 according to the equation log k = ~~611 + log k,.

📜 SIMILAR VOLUMES

Inductivity and Bridging in 2-Bicyclo[2.
Inductivity and Bridging in 2-Bicyclo[2.2.2]octyl Cations. Polar Effects, Part 11
✍ Cyril A. Grob; Pawel Sawlewicz 📂 Article 📅 1984 🏛 John Wiley and Sons 🌐 German ⚖ 616 KB

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].

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Substituents at the remoter 5-position of 2-adamantyl arylsulfonates control solvolysis rates more strongly than substituents at the 4-position.

Polar Effects. Part 14. Inductive Charge
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✍ Rolf Bielmann; Cyril A. Grob; Dieter Küry; Guo Wei Yao 📂 Article 📅 1985 🏛 John Wiley and Sons 🌐 German ⚖ 330 KB

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 th

Norbornanes. Part 20. Inductivity and br
Norbornanes. Part 20. Inductivity and bridging in 2-norbornyl cations
✍ Rolf Bielmann; Francesco Fuso; Cyril A. Grob 📂 Article 📅 1988 🏛 John Wiley and Sons 🌐 German ⚖ 447 KB

As derived from the Hammetr equation log k/ko = pI 'cr ? where k and ko are rate constants for substituted and unsubstituted tosylates, respectively, and u? are inductive substituent constants [2]. The p , values for C(1) in 3 and 4 are presented and discussed in this communication. The dotted lines

Inductivity and bridging in the formatio
Inductivity and bridging in the formation of 2-norbornyl cations
✍ Cyril A. Grob; Pawel Sawlewicz 📂 Article 📅 1984 🏛 Elsevier Science 🌐 French ⚖ 199 KB

The effects of substituents at C5, C6 and C7 on the solvolysis rates of 2-norbornyl p-toluene sulfonates confirm that through space induction is directional and depends on distance and bridging strain.

Inductive charge dispersal in the solvol
Inductive charge dispersal in the solvolysis of 2-exo- and 2-endo-norbornyl toluenesulfonates.
✍ Francesco Fuso; Cyril A. Grob; Pawel Sawlewicz; Yao Guo-Wei 📂 Article 📅 1985 🏛 Elsevier Science 🌐 French ⚖ 197 KB

The effect of substituents at C4, 5, 6 and 7 on solvolysis rates and products of 2-exo-and 2-endo-norbornyl tosylates confirms that differential carbon participation is responsible for varying exo/endo rate and product ratios.