N-substituent effects on the stability of ketenimines

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A homodesmotic reaction was designed to study N-substituent effects on the stability of ketenimines. A good correlation (SE1 = -12.27χBE + 29.81) between N-substituted ketenimine stabilization energies (SE1) and substituent group electronegativity has been found. Both N-substituted and Cβ-substituted ketenimine stabilization energies (SE1 and SE2) have good correlations with Taft's dual-substituent-parameters and modified Swain-Lupton constants. As to N-substituent and Cβ-substituent effects on the stability of ketenimines, σ-donors stabilize ketenimines while σ-acceptors destabilize them; π-acceptors stabilize ketenimines while π-donors destabilize them.

Original languageEnglish
Pages (from-to)847-852
Number of pages6
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number4
Publication statusPublished - 2000 Apr 1

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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