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<p><a href="page.php?w=carbon_suboxide">carbon suboxide</a> (O?C -> C<sup>0</sup> <- C?O), tetraaminoallenes (described using dative bond language as "<a href="page.php?w=carbodicarbenes">carbodicarbenes"; (R<sub>2</sub>N)<sub>2</sub>C -> C<sup>0</sup> <- C(NR<sub>2)<sub>2</sub>), the Ramirez <a href="page.php?w=Hexaphenylcarbodiphosphorane">carbodiphosphorane</a> (Ph<sub>3</sub>P -> C<sup>0</sup> <- PPh<sub>3), and <a href="page.php?w=Bis%28triphenylphosphine%29iminium_chloride">bis(triphenylphosphine)iminium</a> cation (Ph<sub>3</sub>P -> N<sup>+</sup> <- PPh<sub>3), all of which exhibit considerably bent equilibrium geometries, though with a shallow barrier to bending.  Simple application of the normal rules for drawing Lewis structures by maximizing bonding (using electron-sharing bonds) and minimizing formal charges would predict <a href="page.php?w=heterocumulene">heterocumulene</a> structures, and therefore linear geometries, for each of these compounds.  Thus, these molecules are claimed to be better modeled as coordination complexes of <b>:</b>C<b>:</b> (carbon(0) or <a href="page.php?w=carbones">carbone</a>) or <b>:</b>N<b>:</b><sup>+</sup> (mononitrogen cation) with CO, PPh<sub>3</sub>, or N-heterocycliccarbenes as ligands, the lone-pairs on the central atom accounting for the bent geometry.  However, the usefulness of this view is disputed.</-></-></-></-></p><p>
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