A Test for Synergetic Captodative Radical Stabilization | Zendy

Birkhofer Hermann | Zendy; Hädrich Johannes | Zendy; Beckhaus HansDieter | Zendy; Rüchardt Christoph | Zendy

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A Test for Synergetic Captodative Radical Stabilization

Author(s) -

Birkhofer Hermann,

Hädrich Johannes,

Beckhaus HansDieter,

Rüchardt Christoph

Publication year - 1987

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.198705731

Subject(s) - radical , reactivity (psychology) , chemistry , anomer , reaction rate constant , kinetics , medicinal chemistry , stereochemistry , organic chemistry , physics , medicine , alternative medicine , pathology , quantum mechanics

In contrast to predictions based on the concept of captodative radical stabilization , the rate constants k for the formation of the radicals 2 from 1 increase dramatically in the order 2a < 2b < 2c . This order of reactivity is not only determined by the different stabilization of the radicals 2 by the pair of substituents X/Y, but also by attractive (anomeric effect in la ) and repulsive ( 1c ) σ interactions in the ethane derivatives 1 ( a , X = Y = CH 3 O; b , X = CH 3 O, Y = CN; c , X = Y = CN).

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