Chemistry Publications

Title

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.

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