Electron delocalisation and stabilisation in substituted amino- and hydroxypropynyl radicals

Iain MacInnes; John C. Walton

Electron delocalisation and stabilisation in substituted amino- and hydroxypropynyl radicals

Iain MacInnes, John C. Walton^*

^*Corresponding author for this work

School of Chemistry

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

Abstract

A series of aminopropynes, RC≡CCH₂NH₂ (R = H, Me, Bu^t, Me₃Si), RC≡CCH₂N(SiMe ₃)₂, and hydroxypropynes RC≡CCH₂OH (R = H, Me, Bu^t, 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 language	English
Pages (from-to)	1077-1080
Number of pages	4
Journal	Journal of the Chemical Society, Perkin Transactions 2
Issue number	8
Publication status	Published - 1 Dec 1987

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title = "Electron delocalisation and stabilisation in substituted amino- and hydroxypropynyl radicals",

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.",

author = "Iain MacInnes and Walton, \{John C.\}",

year = "1987",

month = dec,

day = "1",

language = "English",

pages = "1077--1080",

journal = "Journal of the Chemical Society, Perkin Transactions 2",

issn = "1472-779X",

publisher = "Royal Society of Chemistry",

number = "8",

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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 - https://www.scopus.com/pages/publications/37049089336

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 -

Electron delocalisation and stabilisation in substituted amino- and hydroxypropynyl radicals

Abstract

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