Synthesis, Structure, Frontier Orbitals and Reactivity of Ph<sub>3</sub>GeN(SiMe<sub>3</sub>)<sub>2</sub>: Rare Crystal Structure of a Germylamine
The germylamine Ph<sub>3</sub>GeN(SiMe<sub>3</sub>)<sub>2</sub> was synthesized from Ph<sub>3</sub>GeCl and LiN(SiMe)<sub>2</sub> and its X-ray crystal structure was determined. This structure represents only the fourth crystallographically characterized germylamine that has been reported. The two sterically encumbering -SiMe<sub>3</sub> groups completely encapsulate the germanium-nitrogen bond and the geometry at the nitrogen atoms is trigonal planar rather than pyramidal. The structure of Ph<sub>3</sub>GeN(SiMe<sub>3</sub>)<sub>2</sub> was calculated using density functional theory and it was found that the HOMO of this molecule is stabilized relative to that of Ph<sub>3</sub>GeNMe<sub>2</sub>, which has been shown to be a highly effective reagent for the amidation of acid fluorides. The steric attributes Ph<sub>3</sub>GeN(SiMe<sub>3</sub>)<sub>2</sub>, coupled with its more stable HOMO relative to Ph<sub>3</sub>GeNMe<sub>2</sub>, prevent its functioning as an amidation reagent for acid fluorides except in the case of benzoyl fluoride.
Authors
- Milan Gembický (ORCID: https://orcid.org/0000-0002-3898-1612)
- C.S. Weinert (ORCID: https://orcid.org/0000-0003-0754-8688)
- Vanessa A. Fortney
- Julia K. Murphy
- Laura M. Levescy
Institutions
- Oklahoma State University (US)
- University of California San Diego (US)
- Oklahoma State University Oklahoma City (US)
Publication Details
- Journal
- Chemistry - An Asian Journal
- Published
- 2024-11-21
- DOI
- https://doi.org/10.1002/asia.202401274
- Primary Topic
- Synthesis and characterization of novel inorganic/organometallic compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Oklahoma State University