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Updated: Jun 7, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
Synthesis, Structure, Frontier Orbitals and Reactivity of Ph3GeN(SiMe3)2: Rare Crystal Structure of a Germylamine
Vanessa A Fortney1, Laura M Levescy1, Julia K Murphy1
1Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma, 74078, USA.
Abstract:
The germylamine Ph3GeN(SiMe3)2 was synthesized from Ph3GeCl and LiN(SiMe)2 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 -SiMe3 groups completely encapsulate the germanium-nitrogen bond and the geometry at the nitrogen atoms is trigonal planar rather than pyramidal. The structure of Ph3GeN(SiMe3)2 was calculated using density functional theory and it was found that the HOMO of this molecule is stabilized relative to that of Ph3GeNMe2, which has been shown to be a highly effective reagent for the amidation of acid fluorides. The steric attributes Ph3GeN(SiMe3)2, coupled with its more stable HOMO relative to Ph3GeNMe2, prevent its functioning as an amidation reagent for acid fluorides except in the case of benzoyl fluoride.
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