Mechanism of Formation of Grignard Reagents

Erwin A. Vogler, R. L. Stein, J. M. Hayes

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Experiment shows that there is no carbon kinetic isotope effect in the formation of CHsMgl from CH3I (k12/k13 = 0.9992, σ = 0.0005). Calculations indicate that an observable isotope effect should accompany this reaction if it proceeds by an inner-sphere electron-transfer mechanism in which breakage of the carbon-halogen bond must be involved in the rate-determining step. Accordingly, it is proposed that the alternative mechanism must be followed, with the rate-determining step involving formation of a radical-ion pair by outer-sphere electron transfer from the magnesium to the organic halide.

Original languageEnglish (US)
Pages (from-to)3163-3166
Number of pages4
JournalJournal of the American Chemical Society
Volume100
Issue number10
DOIs
StatePublished - Jan 1 1978

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Isotopes
Coal breakage
Electrons
Carbon Isotopes
Halogens
Carbon
Magnesium
Ions
Kinetics
Experiments

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Vogler, Erwin A. ; Stein, R. L. ; Hayes, J. M. / Mechanism of Formation of Grignard Reagents. In: Journal of the American Chemical Society. 1978 ; Vol. 100, No. 10. pp. 3163-3166.
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Vogler, EA, Stein, RL & Hayes, JM 1978, 'Mechanism of Formation of Grignard Reagents', Journal of the American Chemical Society, vol. 100, no. 10, pp. 3163-3166. https://doi.org/10.1021/ja00478a034

Mechanism of Formation of Grignard Reagents. / Vogler, Erwin A.; Stein, R. L.; Hayes, J. M.

In: Journal of the American Chemical Society, Vol. 100, No. 10, 01.01.1978, p. 3163-3166.

Research output: Contribution to journalArticle

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