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WIREs Comput Mol Sci
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Carbodicarbenes—divalent carbon(0) compounds exhibiting carbon–carbon donor–acceptor bonds

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Abstract Theoretical and experimental studies of the recently introduced class of divalent carbon(0) compounds CL2, wherein L is a carbene ligand, are described. Carbodicarbenes posses two donor–acceptor bonds between carbene ligands and a bare carbon atom that retains its four valence electrons as two lone pairs. Carbodicarbenes R2C → C ← CR2 are very strong Lewis bases. They are σ‐ and π‐donors and thus may bind to two Lewis bases. © 2011 John Wiley & Sons, Ltd. WIREs Comput Mol Sci 2011 1 869–878 DOI: 10.1002/wcms.53 This article is categorized under: Structure and Mechanism > Molecular Structures

Bonding situation in tetravalent carbon compounds [C(IV), left], carbenes [C(II), middle], and carbones [C(0), right] with indication of the filling of lone‐pair orbitals.

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Orbital interaction model for carbones with transition metal fragments.

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Structurally characterized transition metal complexes of carbodicarbenes.

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Shape and eigenvalues (in eV) of the highest lying occupied molecular orbitals HOMO and HOMO‐1 of 1b, 1d, 2a, and 3b at the BP86/SVP level. (Reprinted with permission from Refs 14, 15. Copyright 2007 Wiley.)

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Optimized structures of 1b, 1d, 3a, and 3b at the BP86/SVP level of theory. Bond lengths in Å, angles in degree. The central CCC angle is given as α and the interplane angle between the NHC ligands is denoted by τ. Experimental data from X‐ray analyses for 1b,19 3a,22 and 3b22 are given in parentheses. The experimental data of 3a refer to the LiBF4 adduct of the compound. (Reprinted with permission from Ref 13. Copyright 2007 Wiley)

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Optimized geometries and relative energies at BP86/TZ2P of the conformations of carbodicarbenes 1a‐H and optimized geometries of the parent allene 4, and the tetraaminoallenes 2a and 2b. Bond lengths are given in Å, angles in degree, and energies in kcal mol−1. Number of imaginary frequencies i are given as well as the point group to which the respective structures belong. The calculated values for 1a‐Me are given in parentheses. (Reprinted with permission from Ref 13. Copyright 2007 Wiley.)

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