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When and how do diaminocarbenes dimerize?

Roger W Alder1, Michael E Blake, Leila Chaker

  • 1School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK. rog.alder@bristol.ac.uk

Angewandte Chemie (International Ed. in English)
|October 1, 2004
PubMed
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Simple diaminocarbene dimerizations are thermodynamically unfavorable due to ring strain. Proton catalysis is the most common mechanism for dimer formation, though alkali metals may also play a role.

Area of Science:

  • Organic Chemistry
  • Computational Chemistry

Background:

  • Uncatalyzed diaminocarbene dimerization lacks clear examples.
  • Understanding factors controlling dimerization thermodynamics and mechanisms is crucial.

Purpose of the Study:

  • Investigate thermodynamic controls on diaminocarbene dimerization.
  • Elucidate mechanisms responsible for observed dimerizations.

Main Methods:

  • Quantum chemical calculations were employed to study dimerization thermodynamics and energy barriers.
  • Comparison of cyclic and acyclic diaminocarbenes.

Main Results:

  • Cyclic diaminocarbenes (five- and six-membered rings) exhibit dimerizations 100 kJ mol(-1) less favorable than acyclic counterparts.
  • Ring strain, specifically bond and torsional angle changes, accounts for this thermodynamic difference.

Related Experiment Videos

  • Diaminocarbenes are kinetically stable but dimerize rapidly via proton catalysis, forming C-protonated dimers.
  • Circumstantial evidence suggests alkali-metal-promoted dimerization is possible.

    • Conclusions:

    • Ring strain significantly impacts diaminocarbene dimerization thermodynamics.
    • Proton catalysis is identified as a primary mechanism for dimer formation.
    • Further investigation into alkali-metal promotion is warranted.