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Solvent nucleophilicity.

Shinya Minegishi1, Shinjiro Kobayashi, Herbert Mayr

  • 1Department Chemie der Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13 (Haus F), D-81377 München, Germany.

Journal of the American Chemical Society
|April 22, 2004
PubMed
Summary

This study quantifies reaction rates for benzhydrylium ions in various solvent mixtures. The findings enable predictable design of Friedel-Crafts reactions using carbocations.

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Area of Science:

  • Physical Organic Chemistry
  • Reaction Kinetics
  • Carbocation Chemistry

Background:

  • Benzhydrylium ions are diarylcarbenium ions crucial in organic synthesis.
  • Understanding their reaction kinetics in diverse solvent systems is essential for reaction optimization.

Purpose of the Study:

  • To determine the reaction rates of benzhydrylium ions in mixed solvents.
  • To establish a quantitative correlation for predicting reaction outcomes.
  • To derive and compare solvent nucleophilicity parameters.

Main Methods:

  • Photometric determination of reaction rates using UV-vis spectroscopy.
  • Stopped-flow and laser flash techniques for kinetic measurements.
  • Analysis of rate constants using the logarithmic correlation log k = s(N + E).

Main Results:

  • First-order rate constants were determined for benzhydrylium ions in water/acetonitrile, methanol/acetonitrile, ethanol/acetonitrile, ethanol/water, and trifluoroethanol/water mixtures.
  • Solvent nucleophilicity parameters (N1) were derived from the kinetic data.
  • A linear correlation was established between the derived N1 values and Kevill's NT nucleophilicity parameters.

Conclusions:

  • The derived N1 nucleophilicity parameters are directly comparable to existing parameters for pi-systems.
  • This facilitates the systematic design of Friedel-Crafts reactions involving solvolytically generated carbocations.
  • The established quantitative relationships enhance predictability in organic synthesis.

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