Substituent effects on stability of ketenimines

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Abstract

An isodesmic reaction was designed to study substituent effects on the stability of ketenimines. A good correlation (ΔE = -11.31 χBE + 31.07) between substituent group electronegativity and the stability of ketenimines has been found. Electropositive substituents stabilize ketenimines while electronegative substituents destabilize ketenimines. Ketenimines gain extra stabilization when their substituents are π acceptors, such as AlH2, BH2, O=CH-, HO2C-, CN, NO2, and HSO2, resulting in the existence of cyano-cation resonance structures. An ynamine resonance structure plays an important role in ketenimine with a lithium substituent.

Original languageEnglish
Pages (from-to)1169-1173
Number of pages5
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number6
DOIs
Publication statusPublished - 1999 Jun

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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