Computational study of bystander effects in the 1,2-H shifts of alkylmethylcarbenes

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Abstract

Bystander substituent effects in the 1,2-H shifts of several singlet alkylmethylcarbenes (CH2Y-C-CH3) have been studied using density functional theory. Bystander effects similar to that of alkylchlorocarbenes were observed. The methyl, halo, and phenyl groups accelerate 1,2-H shifts in the order Ph > F > Me > Cl, Br > H. Singlet/triplet energy separation of these carbenes have also been examined. All studied carbenes have singlet ground states, and the ability of Y groups to stabilize the relative energies of singlet states is F > Cl > Br> Ph > Me > H. (C) 2000 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)39-49
Number of pages11
JournalJournal of Molecular Structure: THEOCHEM
Volume531
Issue number1-3
DOIs
Publication statusPublished - 2000 Oct 23

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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