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.[1]
Alkali metal phenolates, such as sodium phenolate hydrolyze in aqueous solution to form basic solutions.[2] 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.[3] 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.[4]
^Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, p. 506, ISBN978-0-471-72091-1
^Jakubke, Hans-Dieter; Karcher, Ruth (1999). Lexikon der Chemie in drei Bänden, Band 3. Heidelberg: Spektrum Verlag. p. 14. ISBN3-8274-0381-2.
^[1]. Mayr’s Database of Reactivity Parameters. Retrieved July 10, 2019.
^Mayer, Robert J.; Breugst, Martin; Hampel, Nathalie; Ofial, Armin R.; Mayr, Herbert (2019-06-26). "Ambident Reactivity of Phenolate Anions Revisited: A Quantitative Approach to Phenolate Reactivities". Journal of Organic Chemistry. 84 (14): 8837–8858. doi:10.1021/acs.joc.9b01485. PMID 31241938. S2CID 195696760.
^Beyer, Hans; Walter, Wolfgang (1984). Organische Chemie. Stuttgart: S. Hirzel Verlag. pp. 463–464. ISBN3-7776-0406-2.
This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.
phenolates, also, called, phenoxides, anions, salts, esters, phenols, containing, phenolate, they, formed, reaction, phenols, with, strong, base, structural, formula, phenolate, contents, properties, uses, production, salicylic, acid, also, referencespropertie. 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 1 Structural formula of the phenolate ion Contents 1 Properties 2 Uses 2 1 Production of salicylic acid 3 See also 4 ReferencesProperties editMain article sodium phenoxide Alkali metal phenolates such as sodium phenolate hydrolyze in aqueous solution to form basic solutions 2 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 3 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 4 Uses editAlkyl aryl ethers can be synthesized through the Williamson ether synthesis by treating sodium phenolate with an alkyl halide 5 C6H5ONa CH3I C6H5OCH3 NaI C6H5ONa CH3O 2SO2 C6H5OCH3 CH3O SO3Na Production of salicylic acid edit Salicylic acid is produced in the Kolbe Schmitt reaction between carbon dioxide and sodium phenolate nbsp See also editSodium phenolateReferences edit Smith Michael B March Jerry 2007 Advanced Organic Chemistry Reactions Mechanisms and Structure 6th ed New York Wiley Interscience p 506 ISBN 978 0 471 72091 1 Jakubke Hans Dieter Karcher Ruth 1999 Lexikon der Chemie in drei Banden Band 3 Heidelberg Spektrum Verlag p 14 ISBN 3 8274 0381 2 1 Mayr s Database of Reactivity Parameters Retrieved July 10 2019 Mayer Robert J Breugst Martin Hampel Nathalie Ofial Armin R Mayr Herbert 2019 06 26 Ambident Reactivity of Phenolate Anions Revisited A Quantitative Approach to Phenolate Reactivities Journal of Organic Chemistry 84 14 8837 8858 doi 10 1021 acs joc 9b01485 PMID 31241938 S2CID 195696760 Beyer Hans Walter Wolfgang 1984 Organische Chemie Stuttgart S Hirzel Verlag pp 463 464 ISBN 3 7776 0406 2 nbsp This article about an aromatic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Phenolates amp oldid 1184939110, wikipedia, wiki, book, books, library,
