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.
|Number of pages||5|
|Journal||Journal of the Chemical Society. Perkin Transactions 2|
|Publication status||Published - 1999 Jun|
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