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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen

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Volume 81, Issue 4

Issues

Divalent carbon(0) compounds

Gernot Frenking
  • Corresponding author
  • Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse, D-35032 Marburg, Germany
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Ralf Tonner
  • Corresponding author
  • Centre for Theoretical Chemistry and Physics, New Zealand Institute for Advanced Study; Massey University Albany, Private Bag 102904, North Shore City, 0745 Auckland, New Zealand
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2009-01-01 | DOI: https://doi.org/10.1351/PAC-CON-08-11-03

Quantum chemical studies show that there is a class of carbon compounds with the general formular CL2 where the carbon atom retains its four valence electrons as two lone pairs. The C-L bonds come from L → C donor-acceptor interactions where L is a strong σ-donor. Divalent C(0) compounds (carbones) are conceptually different from divalent C(II) compounds (carbenes) and tetravalent carbon compounds, but the bonding situation in a real molecule may be intermediate between the three archetypes. There are molecules like tetraaminoallenes which may be described in terms of two double bonds (R2N)2C=C=C(NR2)2 where the extraordinary donor strength of the dicoordinated carbon atom comes only to the fore through the interactions with protons and Lewis acids. They may be considered as "hidden divalent C(0) compounds". The donor strength of divalent C(0) molecules has been investigated by calculations of the binding energies with protons and with main-group Lewis acids and the bond dissociation energies (BDEs) of transition-metal complexes.

Keywords: bonding analysis; carbenes; carbon compounds; dicoordinated carbon; divalent C(0)

Conference

International Conference on Physical Organic Chemistry (ICPOC-19), International Conference on Physical Organic Chemistry, ICPOC, Physical Organic Chemistry, 19th, Santiago de Compostela, Spain, 2008-07-13–2008-07-18

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About the article

Published Online: 2009-01-01

Published in Print: 2009-01-01


Citation Information: Pure and Applied Chemistry, Volume 81, Issue 4, Pages 597–614, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-08-11-03.

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