page_title: Alkoxide
section_title: Structure
hierarchical_section_title: Alkoxide / Structure
caption_attribution_description: English: Structure of Li4(OBu-t)4(thf)3 cluster from doi 10.1002/anie.201306884.
context_page_description: An alkoxide is the conjugate base of an alcohol
  and therefore consists of an organic group bonded to a negatively charged oxygen atom. They are written as RO⁻, where R is the organic substituent. Alkoxides are strong bases and, when R is not bulky, good nucleophiles and good ligands. Alkoxides, although generally not stable in protic solvents such as water, occur widely as intermediates in various reactions, including the Williamson ether synthesis. Transition metal alkoxides are widely used for coatings and as catalysts.
  Enolates are unsaturated alkoxides derived by deprotonation of a C-H bond adjacent to a ketone or aldehyde. The nucleophilic center for simple alkoxides is located on the oxygen, whereas the nucleophilic site on enolates is delocalized onto both carbon and oxygen sites. Ynolates are also unsaturated alkoxides derived from acetylenic alcohols.
  Phenoxides are close relatives of the alkoxides, in which the alkyl group is replaced by a derivative of benzene. Phenol is more acidic than a typical alcohol; thus, phenoxides are correspondingly less basic and less nucleophilic than alkoxides.
context_section_description: Alkali metal alkoxides are often oligomeric or polymeric compounds, especially when the R group is small (Me, Et).  The alkoxide anion is a good bridging ligand, thus many alkoxides feature M₂O or M₃O linkages.  In solution, the alkali metal derivatives exhibit strong ion-pairing, as expected for the alkali metal derivative of a strongly basic anion.
caption: Structure of the Li4(OBu-t)4(thf)3 cluster, highlighting the tendency of alkoxides to aggregate and bind ether ligands.[5]  Color code: dark gray = C, violet = Li, red = O, light gray = H.
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