Electron delocalisation and stabilisation in substituted amino- and hydroxypropynyl radicals

Iain MacInnes, John C. Walton*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)

Abstract

A series of aminopropynes, RC≡CCH2NH2 (R = H, Me, But, Me3Si), RC≡CCH2N(SiMe 3)2, and hydroxypropynes RC≡CCH2OH (R = H, Me, But, Me3Si, CF3, and EtO2C), were prepared and the corresponding α-aminopropynyl and α-hydroxypropynyl radicals were examined by e.s.r. spectroscopy. For the first series, the C-N bond rotation barriers were determined from the exchange broadening in the spectra and hence radical stabilisation energies were estimated. The spin distribution in these series indicated an extra delocalisation in radicals with captodative substitution.

Original languageEnglish
Pages (from-to)1077-1080
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number8
Publication statusPublished - 1 Dec 1987

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