Substituent effects on stability of ketenimines

Kuangsen Sung

doi:10.1039/a900288j

Substituent effects on stability of ketenimines

Kuangsen Sung

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

An isodesmic reaction was designed to study substituent effects on the stability of ketenimines. A good correlation (ΔE = -11.31 χ_BE + 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 language	English
Pages (from-to)	1169-1173
Number of pages	5
Journal	Journal of the Chemical Society. Perkin Transactions 2
Issue number	6
DOIs	https://doi.org/10.1039/a900288j
Publication status	Published - 1999 Jun

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1039/a900288j

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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.",

author = "Kuangsen Sung",

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AB - 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.

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Substituent effects on stability of ketenimines

Abstract

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