Tetra(amino)methanes: Implications of their structure and reactivity pattern for hypothetical carbon nitride frameworks

Alexander Jockisch, Annette Schier, Hubert Schmidbaur

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Because of their possible role as model compounds for the structural units of carbon nitride C3N4, the preparation, structural chemistry, and some representative reactions of tetra(amino)methanes have been (re)investigated. In the crystal, C(NMe2)4 (1) has a molecular geometry close to D2d symmetry as proposed by theoretical calculations using state-of-the-art density functional methods. The coordination of the central carbon atom is distorted tetrahedral and the configuration of the nitrogen atoms is strongly pyramidal, as opposed to almost planar in the tetra(amino)silanes. Tetra(pyrrolidinyljmethane has a similar core structure, with all heterocyclic substituents in an envelop conformation flexible in solution. Tetra(piperidinyl)methane is more rigid in solution, owing to a more congested structure, with much higher inversion barriers for the six-membered rings. Hydrolysis of 1 leads to Me2NH and hexamethylguanidinium hydroxide, and treatment of 1 with HAuCl4(aq) affords crystalline [C(NMe2)3]+ AuCl4-, the structure of which has also been determined. Compound 1 is a strong nucleophile and can be used as an aminating agent, converting e.g. halosilanes into dimethylaminosilanes, with the guanidinium cation as the leaving group. The experimental results are discussed in the light of recent predictions regarding bulk carbon nitrides.

Original languageEnglish
Pages (from-to)1739-1744
Number of pages6
JournalChemische Berichte
Issue number12
StatePublished - 1997
Externally publishedYes


  • Amination
  • Carbon nitride
  • Conformation analysis
  • Guanidinium salts
  • Tetra(amino)methanes


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