Organosodium chemistry

This polarity results from the disparate electronegativity of carbon (2.55) and that of lithium 0.98, sodium 0.93 potassium 0.82 rubidium 0.82 caesium 0.79).

One consequence of the highly polarized Na-C bond is that simple organosodium compounds often exist as polymers that are poorly soluble in solvents.

Because of its large radius, Na prefers a higher coordination number than does lithium in organolithium compounds.

Crystals have been shown to consist of chains of alternating Na(TMEDA)+ and CH2SiMe−3 groups with Na–C distances ranging from 2.523(9) to 2.643(9) Å.

[6] Organosodium compounds are traditionally used as strong bases,[9] although this application has been supplanted by other reagents such as sodium bis(trimethylsilyl)amide.

[16] A similar Wurtz coupling-like reaction is the basis of the industrial route to triphenylphosphine: The polymerization of butadiene and styrene is catalyzed by sodium metal.

Reminiscent of the nickel arsenide structure, MCH3 (M = K, Rb, Cs) has six alkali metal centers bound to each methyl group.