Endor investigations on the capto-dative stabilisation of triphenylmethyl radicals

Lehnig, M.; Stewen, U.

doi:10.1016/s0040-4039(01)80323-3

Cited by 5 publications

(1 citation statement)

References 12 publications

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“…Recently, a number of reports on the chemistry of TAM radicals have been published. − Renewed research efforts in the area are directed at the investigation of the resonance stabilization and “captodative” stabilization of stable radicals. , ESR and ENDOR are the major methods used for the investigations. The hyperfine coupling constants of TAM radicals depend on the overall conformation of the molecule.…”

Section: Introductionmentioning

confidence: 99%

Photochemistry and Photophysics of (p-Benzoylphenyl)diphenylmethyl and (p-Benzoylphenyl)bis(4-tert-butylphenyl)methyl Radicals in Different Solvents

2000

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The photochemical reactions of (p-benzoylphenyl)diphenylmethyl (1) and (p-benzoylphenyl)bis(4-tert-butylphenyl)methyl (2) in various solvents were investigated. The photophysical parameters of the first excited doublet state of the radicals were measured using spectroscopic and kinetic methods and led to a “molecular rotor” model to characterize the excited-state behavior. The charge-transfer excited state for both radicals was observed. Photoproducts separated from the photolysis of 1 and 2 in benzene suggest photodecomposition proceeds via H-abstraction (55%), fragmentation (20%), cyclization (10%), and addition (10%).

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Section: Introductionmentioning

confidence: 99%

Photochemistry and Photophysics of (p-Benzoylphenyl)diphenylmethyl and (p-Benzoylphenyl)bis(4-tert-butylphenyl)methyl Radicals in Different Solvents

2000

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ENDOR‐Untersuchungen zur capto‐dativen Stabilisierung phenoxysubstituierter Triphenylmethylradikale

Stewen¹,

Lehnig²

1989

Chem. Ber.

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Fiir pdisubstituierte Triphenylmethylradikale 1 mit R = OPh, R' = CF3, CN, Ph ergeben sich aus den ENDOR-Daten Stabilisieruogen von 0.6, 1.2 bzw. <0.2 kcal/mol gegeouber den bei Additivitat der Substituenteneiofliisse zu erwartenden Werten, entsprechend dem cupto-dutiuen Konzept. Dieses gilt generell fir Radikale 1 rnit R,R = OPh, tBu, Ph, SMe, COPh, CF,, CN. Radikale 1 mit R = OMe zeigen ein abweichendes Verhalten.

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Influence of polar substituents on the Antioxidant Properties of para-Vinyl Phenols and on the stabilization of the corresponding phenoxy radicals

Borghese¹,

Merényi²,

Penelle³

et al. 1992

J. Prakt. Chem.

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Phenols 1 substituted in the para position by vinyl groups bearing different combinations of thioether and cyano substituents in the β positions were synthesized. The determination of their efficiency as antioxidants led to the following order of reactivity: RS,RS ≫ RS,CN > CN,CN. The analysis of the ESR spectra of analogous phenoxy radicals 4 indicates however a different order for the radical stabilization: RS,CN > RS,RS ≫ CN,CN. This behavior is explained by a charge or electron transfer in the transition state as the main factor governing the reactivity. Relative stabilizations of the phenoxy radicals are easily explained according to the captodative concept.

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Endor investigations on the capto-dative stabilisation of triphenylmethyl radicals

Cited by 5 publications

References 12 publications

Photochemistry and Photophysics of (p-Benzoylphenyl)diphenylmethyl and (p-Benzoylphenyl)bis(4-tert-butylphenyl)methyl Radicals in Different Solvents

Photochemistry and Photophysics of (p-Benzoylphenyl)diphenylmethyl and (p-Benzoylphenyl)bis(4-tert-butylphenyl)methyl Radicals in Different Solvents

ENDOR‐Untersuchungen zur capto‐dativen Stabilisierung phenoxysubstituierter Triphenylmethylradikale

Influence of polar substituents on the Antioxidant Properties of para-Vinyl Phenols and on the stabilization of the corresponding phenoxy radicals

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