TY - JOUR
T1 - Electron delocalisation and stabilisation in substituted amino- and hydroxypropynyl radicals
AU - MacInnes, Iain
AU - Walton, John C.
PY - 1987/12/1
Y1 - 1987/12/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=37049089336&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:37049089336
SN - 1472-779X
SP - 1077
EP - 1080
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
IS - 8
ER -