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Diastereomeric Differentiation in the Quenching of Excited States by Hydrogen Donors
Author(s) -
Pischel Uwe,
Abad Sergio,
Domingo Luis R.,
Boscá Francisco,
Miranda Miguel A.
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200250442
Subject(s) - diastereomer , chemistry , ketone , quenching (fluorescence) , reaction rate constant , excited state , hydrogen , photochemistry , stereochemistry , kinetics , organic chemistry , physics , fluorescence , atomic physics , optics , quantum mechanics
Chiral dyads of ( S )‐ketoprofen and ( S )‐ or ( R )‐tetrahydrofurfurylamine show diastereomeric differentiation in photoinduced hydrogen abstractions, which could be directly followed by time‐resolved observation of the ketone triplet state. A unimolecular rate constant of k H =3.0×10 5 s −1 was found for the S , S diastereomer, while the S , R diastereomer reacts four times slower ( k H =7.5×10 4 s −1 ).