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Alkoxide
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<p>In <a href="/facts/Chemistry/SrNqkGVm">chemistry</a>, an alkoxide is the <a href="/facts/Conjugate_base/hohgQ07M">conjugate base</a> of an <a href="/facts/Alcohol_(chemistry)/Y0SCTDkh">alcohol</a> and therefore consists of an organic group bonded to a negatively charged <a href="/facts/Oxygen/acyn6o8r">oxygen</a> atom. They are written as RO−, where R is the <a href="/facts/Organyl/gqCNaN45">organyl</a> <a href="/facts/Substituent/6y9IE6G0">substituent</a>. Alkoxides are strong <a href="/facts/Base_(chemistry)/M9wA7qeM">bases</a> and, when R is not <a href="/facts/Non-nucleophilic_base/zqaXQboq">bulky</a>, good <a href="/facts/Nucleophile/xYccoaJQ">nucleophiles</a> and good <a href="/facts/Ligand/6etB3qeW">ligands</a>. Alkoxides, although generally not stable in <a href="/facts/Protic_solvent/oSApp96e">protic solvents</a> such as water, occur widely as intermediates in various reactions, including the <a href="/facts/Williamson_ether_synthesis/QLmp8Qcw">Williamson ether synthesis</a>. <a href="/facts/Transition_metal/0slGWoLQ">Transition metal</a> alkoxides are widely used for coatings and as <a href="/facts/Catalyst/LPBS7TQC">catalysts</a>. </p><p><a href="/facts/Enolate/D13WdFNR">Enolates</a> are unsaturated alkoxides derived by deprotonation of a C−H bond adjacent to a <a href="/facts/Ketone/BqQXpLo4">ketone</a> or <a href="/facts/Aldehyde/xSIRkW03">aldehyde</a>. 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. <a href="/facts/Ynolate/lPXEMufI">Ynolates</a> are also unsaturated alkoxides derived from acetylenic alcohols. </p><p><a href="/facts/Phenoxides/b5pKVn1X">Phenoxides</a> are close relatives of the alkoxides, in which the alkyl group is replaced by a phenyl group. <a href="/facts/Phenol/ACJs5NIU">Phenol</a> is more acidic than a typical alcohol; thus, phenoxides are correspondingly less basic and less nucleophilic than alkoxides. They are, however, often easier to handle and yield derivatives that are more crystalline than those of the alkoxides. </p>