The germylamine PhGeN(SiMe) was synthesized from PhGeCl and LiN(SiMe) 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 groups completely encapsulate the germanium-nitrogen bond and the geometry at the nitrogen atoms is trigonal planar rather than pyramidal. The structure of PhGeN(SiMe) was calculated using density functional theory and it was found that the HOMO of this molecule is stabilized relative to that of PhGeNMe, which has been shown to be a highly effective reagent for the amidation of acid fluorides. The steric attributes PhGeN(SiMe), coupled with its more stable HOMO relative to PhGeNMe, prevent its functioning as an amidation reagent for acid fluorides except in the case of benzoyl fluoride.
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