Aromatic Azide Transformation on the Ag(111) Surface Studied by Scanning Probe Microscopy.
azides
density functional calculations
on-surface chemistry
scanning probe microscopy
silver surface
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
18 Feb 2019
18 Feb 2019
Historique:
received:
26
10
2018
pubmed:
3
1
2019
medline:
3
1
2019
entrez:
3
1
2019
Statut:
ppublish
Résumé
Chemical transformation of 9-azidophenanthrene on the Ag(111) surface was studied by nc-AFM in UHV. High-resolution imaging supported by first-principle calculations revealed the structure of the final products that originated from a common and elusive 9-phenanthryl nitrenoid intermediate chemisorbed on the Ag(111) surface. A formal nitrene insertion into the C-H bond along with its dimerisation and hydrogenation were identified as main reaction channels. Thus, the ability of aryl azides to form covalent σ- and π-bonds between their transformation products on a solid surface was demonstrated at a single-molecule level.
Identifiants
pubmed: 30600888
doi: 10.1002/anie.201812334
doi:
Types de publication
Journal Article
Langues
eng
Pagination
2266-2271Subventions
Organisme : Grantová Agentura České Republiky
ID : 16-08294S
Organisme : Grantová Agentura České Republiky
ID : 18-09914S
Organisme : Ústav Organické Chemie a Biochemie, Akademie Věd České Republiky
ID : RVO: 61388963
Organisme : Akademie Věd České Republiky
ID : Praemium Academie
Organisme : Ministerstvo Školství, Mládeže a Tělovýchovy
ID : LM2015087
Organisme : Ministerstvo Školství, Mládeže a Tělovýchovy
ID : SOLID21-CZ.02.1.01/0.0/0.0/16_019/0000760
Organisme : National Grid Infrastructure MetaCentrum
ID : CESNET LM2015042
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.