{{Short description|Salts or other derivatives of phenols}} 150px|thumb|Structural formula of the phenolate ion '''Phenolates''' (also called '''phenoxides''') are anions, salts, and esters of phenols, containing the phenolate ion. They may be formed by reaction of phenols with strong base.<ref>{{March6th|page = 506}}</ref>
== Properties == {{main|sodium phenoxide}} Alkali metal phenolates, such as sodium phenolate hydrolyze in aqueous solution to form basic solutions.<ref>{{Cite book|last1=Jakubke|first1=Hans-Dieter|title=Lexikon der Chemie in drei Bänden, Band 3|last2=Karcher|first2=Ruth|publisher=Spektrum Verlag|year=1999|isbn=3-8274-0381-2|location=Heidelberg|pages=14}}</ref> At pH = 10, phenol and phenolate are in approximately 1:1 proportions.
The phenoxide anion (aka phenolate) is a strong nucleophile with a comparable to the one of carbanions or tertiary amines.<ref>[https://www.cup.lmu.de/oc/mayr/reaktionsdatenbank2/]. Mayr's Database of Reactivity Parameters. Retrieved July 10, 2019.</ref> Generally, oxygen attack of phenoxide anions is kinetically favored, while carbon-attack is thermodynamically preferred (see Thermodynamic versus kinetic reaction control). Mixed oxygen/carbon attack and by this a loss of selectivity is usually observed if the reaction rate reaches diffusion control.<ref>{{cite journal|last1=Mayer|first1=Robert J.|last2=Breugst|first2=Martin|last3=Hampel|first3=Nathalie|last4=Ofial|first4=Armin R.|last5=Mayr|first5=Herbert|date=2019-06-26|title=Ambident Reactivity of Phenolate Anions Revisited: A Quantitative Approach to Phenolate Reactivities|journal=Journal of Organic Chemistry|volume=84|issue=14|pages=8837–8858|doi=10.1021/acs.joc.9b01485|pmid=31241938|s2cid=195696760}}</ref>
== Uses == Alkyl aryl ethers can be synthesized through the Williamson ether synthesis by treating sodium phenolate with an alkyl halide:<ref name="Beyer">{{Cite book|last1=Beyer|first1=Hans|title=Organische Chemie|last2=Walter|first2=Wolfgang|publisher=S. Hirzel Verlag|year=1984|isbn=3-7776-0406-2|location=Stuttgart|pages=463–464}}</ref> :C<sub>6</sub>H<sub>5</sub>ONa + CH<sub>3</sub>I → C<sub>6</sub>H<sub>5</sub>OCH<sub>3</sub> + NaI :C<sub>6</sub>H<sub>5</sub>ONa + (CH<sub>3</sub>O)<sub>2</sub>SO<sub>2</sub> → C<sub>6</sub>H<sub>5</sub>OCH<sub>3</sub> + (CH<sub>3</sub>O)SO<sub>3</sub>Na
=== Production of salicylic acid === Salicylic acid is produced in the Kolbe–Schmitt reaction between carbon dioxide and sodium phenolate.
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== See also == * Sodium phenolate
== References == {{Reflist}}
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Category:Phenolates