TY - JOUR
T1 - Selective Activation of Methyl C–H Bonds of Toluene by Oxygen on Metallic Gold
AU - Rodríguez-Reyes, Juan Carlos F.
AU - Friend, Cynthia M.
AU - Madix, Robert J.
N1 - Publisher Copyright:
© 2018, Springer Science+Business Media, LLC, part of Springer Nature.
PY - 2018/7/1
Y1 - 2018/7/1
N2 - Abstract: 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 C6H5CHD2, 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, CO2 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: [Figure not available: see fulltext.]
AB - Abstract: 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 C6H5CHD2, 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, CO2 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: [Figure not available: see fulltext.]
UR - http://www.scopus.com/inward/record.url?scp=85047108232&partnerID=8YFLogxK
U2 - 10.1007/s10562-018-2407-3
DO - 10.1007/s10562-018-2407-3
M3 - Article
AN - SCOPUS:85047108232
SN - 1011-372X
VL - 148
SP - 1985
EP - 1989
JO - Catalysis Letters
JF - Catalysis Letters
IS - 7
ER -