Selective Activation of Methyl C–H Bonds of Toluene by Oxygen on Metallic Gold

In accord with its gas phase acidity, toluene is activated by atomic oxygen adsorbed on Au(111) at the methyl C–H bonds. Titration of this species from the surface with HCOOD yields C 6 H 5 CHD 2 , indicating that much of the toluene has been doubly deprotonated at the methyl carbon. Even at low sur...

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Bibliographic Details
Published in:Catalysis letters 2018-07, Vol.148 (7), p.1985-1989
Main Authors: Rodríguez-Reyes, Juan Carlos F., Friend, Cynthia M., Madix, Robert J.
Format: Article
Language:English
Subjects:
Activated carbon
Atomic oxygen
Benzoates
Benzoic acid
Catalysis
Chemistry
Chemistry and Materials Science
Industrial Chemistry/Chemical Engineering
Organic acids
Organometallic Chemistry
Physical Chemistry
Room temperature
Titration
Toluene
Vapor phases
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Summary:In accord with its gas phase acidity, toluene is activated by atomic oxygen adsorbed on Au(111) at the methyl C–H bonds. Titration of this species from the surface with HCOOD yields C 6 H 5 CHD 2 , indicating that much of the toluene has been doubly deprotonated at the methyl carbon. Even at low surface coverages of atomic oxygen the thusly-activated species yields only CO, CO 2 and water as gas phase products when heated above room temperature, indicating the facile formation of an adsorbed benzoate, not simple oxygen insertion into the carbene to form benzyl benzyloxy. At higher O pre-coverages benzoic acid forms between 400 and 500 K. Graphical Abstract
ISSN:1011-372X
1572-879X
DOI:10.1007/s10562-018-2407-3