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Siloxide

Siloxides are chemical compounds with the formula R<sub>3</sub>SiOM, where R is usually an organic group and M is usually a metal cation. Also called silanolates, they are derived by deprotonation of silanols. They also arise by the degradation of siloxanes by base:

R<sub>3</sub>SiOSiR<sub>3</sub> + 2 NaOH → 2 R<sub>3</sub>SiONa + H<sub>2</sub>O

Cleavage of cyclic siloxanes affords siloxides:

(Me<sub>2</sub>SiO)<sub>3</sub> + MeLi → Me<sub>3</sub>SiOSiMe<sub>2</sub>OSiMe<sub>2</sub>OLi

These anions function as ligands for metal ions, forming complexes similar to metal alkoxides. Sodium trimethylsiloxide is useful for generating metal complexes by salt metathesis reactions. A very bulky siloxide is tert-butyl<sub>3</sub>SiO<sup>−</sup>, sometimes called silox.

Siloxides are weaker net donors than alkoxides because p<sub>π</sub>-d donation has to compete with backbonding from the oxygen atom into the low-lying Si-C σ<sup>*</sup> orbitals.

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