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Measuring the Relative Reactivity of the Carbon–Hydrogen Bonds of Alkanes as Nucleophiles
Author(s) -
Olmos Andrea,
Gava Riccardo,
Noverges Bárbara,
Bellezza Delia,
Jacob Kane,
Besora Maria,
Sameera W. M. Chamil,
Etienne Michel,
Maseras Feliu,
Asensio Gregorio,
Caballero Ana,
Pérez Pedro J.
Publication year - 2018
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.201807448
Subject(s) - electrophile , nucleophile , alkane , chemistry , reactivity (psychology) , methane , rhodium , bond cleavage , carbon fibers , hydrogen bond , hydrogen , organic chemistry , medicinal chemistry , photochemistry , hydrocarbon , molecule , catalysis , materials science , medicine , alternative medicine , pathology , composite number , composite material
We report quantitative measurements of the relative reactivities of a series of C−H bonds of gaseous or liquid C n H 2 n +2 alkanes ( n =1–8, 29 different C−H bonds) towards in situ generated electrophiles (copper, silver, and rhodium carbenes), with methane as the reference. This strategy surpasses the drawback of previous model reactions of alkanes with strong electrophiles suffering from C−C cleavage processes, which precluded direct comparison of the relative reactivities of alkane C−H bonds.