Chemistry Publications
The Addition of Nitriles to a Molecular Digermene: Reversible Addition and Comparison to Surface Reactivity
Document Type
Article
Publication Date
5-1-2015
Journal
Angewandte Chemie - International Edition
Volume
54
Issue
22
First Page
6600
Last Page
6603
URL with Digital Object Identifier
10.1002/anie.201501278
Abstract
The addition of acetonitrile, propionitrile, and acrylonitrile to tetramesityldigermene was investigated and compared to the addition of acetonitrile and acrylonitrile to germanium dimers on the Ge(100)-2×1 surface. In each case, a 1,2,3-azadigermetine was formed as the major product. As on the surface, the addition of nitriles to digermenes was found to be reversible, providing the first example of a reversible cycloaddition of a ditetrelene. No evidence for a six-membered cyclic ketenimine was observed as noted in the surface chemistry, suggesting that the surface ketenimine might only form between two adjacent dimers rather than on a single dimer. The comparative chemistry provides important insights that are not possible by the independent study of each system. A tale of two digermenes: The addition of acetonitrile, propionitrile, and acrylonitrile to tetramesityldigermene was examined to compare the structures of the molecular adducts with the structures of the nitrile adducts formed on the Ge(100)-2×1 surface and to provide further insight into the surface chemistry. The addition of nitriles was found to be reversible, and no evidence for cyclic ketenimines was found.