Kinetic applications of electron paramagnetic resonance spectroscopy. 25. Radicals formed by spin trapping with di-tert-butyl thioketone

Scaiano, J. C.; Ingold, K. U.

doi:10.1021/ja00432a006

Cited by 81Electron Spin Resonance StudiesChemical Reactions and MechanismsChemical Reaction Mechanisms

Kinetic applications of electron paramagnetic resonance spectroscopy. 25. Radicals formed by spin trapping with di-tert-butyl thioketone

Scaiano, J. C., Ingold, K. U.·1976·Journal of the American Chemical Society

DOI 10.1021/ja00432a006

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Abstract

A variety of transient RnM· radicals (M = C, Si, Sn, and P, but not O) have been trapped with di-tert-butyl thioketone and the persistent adduct radicals, RnMSĊ(CMe3)2 (1). have been examined by EPR spectroscopy. From a comparison of the hyperfine splittings by M in 1 and in RnMCH2Ċ(CMe3)2 and analogous radicals, and from a consideration of the g values for 1 (2.0024-2.0033), it is concluded that the RnM group eclipses the Cα 2pz orbital. Competitive experiments involving the reaction of tert-butyl with thione or oxygen at -80°C and the reaction of methyl with thione or Me3CNO at -40°C indicate that alkyl addition to the thione has a rate constant of ca. 106 M-1 s-1 at these temperatures. The CH3SĊ(CMe3)2 radial exists in equilibrium with a dimer at temperatures in the range -70 to -110°C: ΔH = 9.6 ± 1.5 kcal/mol; ΔS = 32 ± 3 gibbs/mol. Above -50°C the CH3SĊ(CMe3)2 radical decays with the first-order kinetics. It is concluded that CH3SĊ(CMe3)2 and SiH3SĊ(CMe3)2 decay by an intramolecular transfer of H from M to Cα. The CF3SĊ(CMe3)2 radical is extremely persistent. The (n-Bu)3SnSĊ(CMe3)2 radical decays with second-order kinetics. Arrhenius parameters for some of the decay reactions are reported.

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Direct radical addition reactions of thiocarbonyl (C=S) groups unaccompanied by β-scission have rarely been reported.
“Direct radical addition reactions of thiocarbonyl (C=S) groups unaccompanied by β-scission have rarely been reported despite their potential for constructing various sulfur-containing compounds.”
From Direct Radical Copolymerizations of Thioamides To Generate Vinyl Polymers with Degradable Thioether Bonds in the Backbones (2023) · cites this paper as [7]

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Authors: Scaiano, J. C., & Ingold, K. U.
ORCID: Scaiano, J. C.
Venue: Journal of the American Chemical Society
Publisher: American Chemical Society (ACS)
Published: 1976-08
Volume: 98
Issue: 16
Pages: 4727-4732
ISSN: 0002-7863 (ISSN-L)
1520-5126
DOI: 10.1021/ja00432a006
OpenAlex: W2951691971
Cited by: 81
References: 0
Citations by year: 2026: 2 · 2024: 1 · 2023: 1 · 2022: 1 · 2021: 3 · 2020: 2 · 2019: 2 · 2018: 2 · 2013: 1 · 2012: 3
FWCI: 1.57
Type: journal article
Language: en
Open access: closed
Locations: Journal of the American Chemical Society (publishedVersion)
NPARC (submittedVersion)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Biophysics › Electron Spin Resonance Studies
Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Chemical Reactions and Mechanisms
Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
Keywords: spin trapping, transient radicals, hyperfine splitting, g-value, radical dimerization, radical decay kinetics, intramolecular hydrogen transfer, tert-butyl radical, methyl radical, silicon radicals, phosphorus radicals, Arrhenius parameters

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Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

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Kinetic applications of electron paramagnetic resonance spectroscopy. 25. Radicals formed by spin trapping with di-tert-butyl thioketone

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Integrity signals

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