Sodium phenoxide (sodium phenolate) is an organic compound with the formula NaOC6H5. It is a white crystalline solid. Its anion, phenoxide, also known as phenolate, is the conjugate base of phenol. It is used as a precursor to many other organic compounds, such as aryl ethers.
Most commonly, solutions of sodium phenoxide are produced by treating phenol with sodium hydroxide.[2] Anhydrous derivatives can be prepared by combining phenol and sodium. A related, updated procedure uses sodium methoxide instead of sodium hydroxide:[3]
NaOCH3 + HOC6H5 → NaOC6H5 + HOCH3
Sodium phenoxide can also be produced by the "alkaline fusion" of benzenesulfonic acid, whereby the sulfonate groups are displaced by hydroxide:
C6H5SO3Na + 2 NaOH → C6H5OH + Na2SO3
This route once was the principal industrial route to phenol.[citation needed]
Structureedit
Like other sodium alkoxides, solid sodium phenoxide adopts a complex structure involving multiple Na-O bonds. Solvent-free material is polymeric, each Na center being bound to three oxygen ligands as well as the phenyl ring. Adducts of sodium phenoxide are molecular, such as the cubane-type cluster [NaOPh]4(HMPA)4.[4]
Part of the crystal structure of pure sodium phenoxide
Subunit of the crystal structure of pure sodium phenoxide, illustrating the binding of phenoxide ions to sodium through both the oxygen and the arene.
Reactionsedit
Sodium phenoxide is a moderately strong base. Acidification gives phenol:[5]
PhOH ⇌ PhO− + H+ (K = 10−10)
The acid-base behavior is complicated by homoassociation, reflecting the association of phenol and phenoxide.[6]
Sodium phenoxide reacts with alkylating agents to afford alkyl phenyl ethers:[2]
NaOC6H5 + RBr → ROC6H5 + NaBr
The conversion is an extension of the Williamson ether synthesis. With acylating agents, one obtains phenyl esters:
NaOC6H5 + RC(O)Cl → RCO2C6H5 + NaCl
Sodium phenoxide is susceptible to certain types of electrophilic aromatic substitutions. For example, it reacts with carbon dioxide to form 2-hydroxybenzoate, the conjugate base of salicylic acid. In general however, electrophiles irreversibly attack the oxygen center in phenoxide.
^ abC. S. Marvel; A. L. Tanenbaum (1929). "γ-Phenoxypropyl Bromide". Org. Synth. 9: 72. doi:10.15227/orgsyn.009.0072.
^Kornblum, Nathan; Lurie, Arnold P. (1959). "Heterogeneity as a Factor in the Alkylation of Ambident Anions: Phenoxide Ions1,2". Journal of the American Chemical Society. 81 (11): 2705–2715. doi:10.1021/ja01520a030.
^Michael Kunert, Eckhard Dinjus, Maria Nauck, Joachim Sieler "Structure and Reactivity of Sodium Phenoxide - Following the Course of the Kolbe-Schmitt Reaction" Chemische Berichte 1997 Volume 130, Issue 10, pages 1461–1465. doi:10.1002/cber.19971301017
^Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN978-0-471-72091-1
Media related to Sodium phenoxide at Wikimedia Commons
March 16, 2024
sodium, phenoxide, sodium, phenolate, organic, compound, with, formula, naoc6h5, white, crystalline, solid, anion, phenoxide, also, known, phenolate, conjugate, base, phenol, used, precursor, many, other, organic, compounds, such, aryl, ethers, namespreferred,. Sodium phenoxide sodium phenolate is an organic compound with the formula NaOC6H5 It is a white crystalline solid Its anion phenoxide also known as phenolate is the conjugate base of phenol It is used as a precursor to many other organic compounds such as aryl ethers Sodium phenoxide NamesPreferred IUPAC name Sodium phenoxide 1 Other names Sodium phenolateIdentifiersCAS Number 139 02 6 Y3D model JSmol Interactive imageChemSpider 8420ECHA InfoCard 100 004 862PubChem CID 4445035UNII 4NC0T56V35 YCompTox Dashboard EPA DTXSID4027072InChI InChI 1S C6H6O Na c7 6 4 2 1 3 5 6 h1 5 7H q 1 p 1Key NESLWCLHZZISNB UHFFFAOYSA MInChI 1 C6H6O Na c7 6 4 2 1 3 5 6 h1 5 7H q 1 p 1Key NESLWCLHZZISNB REWHXWOFAPSMILES Na O c1ccccc1PropertiesChemical formula C6H5NaOMolar mass 116 09 g molAppearance White solidHazardsOccupational safety and health OHS OSH Main hazards Harmful CorrosiveFlash point Non flammableAutoignitiontemperature Non flammableExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Synthesis and structure 2 Structure 3 Reactions 4 References 5 External linksSynthesis and structure editMost commonly solutions of sodium phenoxide are produced by treating phenol with sodium hydroxide 2 Anhydrous derivatives can be prepared by combining phenol and sodium A related updated procedure uses sodium methoxide instead of sodium hydroxide 3 NaOCH3 HOC6H5 NaOC6H5 HOCH3Sodium phenoxide can also be produced by the alkaline fusion of benzenesulfonic acid whereby the sulfonate groups are displaced by hydroxide C6H5SO3Na 2 NaOH C6H5OH Na2SO3This route once was the principal industrial route to phenol citation needed Structure editLike other sodium alkoxides solid sodium phenoxide adopts a complex structure involving multiple Na O bonds Solvent free material is polymeric each Na center being bound to three oxygen ligands as well as the phenyl ring Adducts of sodium phenoxide are molecular such as the cubane type cluster NaOPh 4 HMPA 4 4 nbsp Part of the crystal structure of pure sodium phenoxide nbsp Subunit of the crystal structure of pure sodium phenoxide illustrating the binding of phenoxide ions to sodium through both the oxygen and the arene Reactions editSodium phenoxide is a moderately strong base Acidification gives phenol 5 PhOH PhO H K 10 10 The acid base behavior is complicated by homoassociation reflecting the association of phenol and phenoxide 6 Sodium phenoxide reacts with alkylating agents to afford alkyl phenyl ethers 2 NaOC6H5 RBr ROC6H5 NaBrThe conversion is an extension of the Williamson ether synthesis With acylating agents one obtains phenyl esters NaOC6H5 RC O Cl RCO2C6H5 NaClSodium phenoxide is susceptible to certain types of electrophilic aromatic substitutions For example it reacts with carbon dioxide to form 2 hydroxybenzoate the conjugate base of salicylic acid In general however electrophiles irreversibly attack the oxygen center in phenoxide nbsp The Kolbe Schmitt reaction References edit International Union of Pure and Applied Chemistry 2014 Nomenclature of Organic Chemistry IUPAC Recommendations and Preferred Names 2013 The Royal Society of Chemistry pp 1071 1129 doi 10 1039 9781849733069 ISBN 978 0 85404 182 4 a b C S Marvel A L Tanenbaum 1929 g Phenoxypropyl Bromide Org Synth 9 72 doi 10 15227 orgsyn 009 0072 Kornblum Nathan Lurie Arnold P 1959 Heterogeneity as a Factor in the Alkylation of Ambident Anions Phenoxide Ions1 2 Journal of the American Chemical Society 81 11 2705 2715 doi 10 1021 ja01520a030 Michael Kunert Eckhard Dinjus Maria Nauck Joachim Sieler Structure and Reactivity of Sodium Phenoxide Following the Course of the Kolbe Schmitt Reaction Chemische Berichte 1997 Volume 130 Issue 10 pages 1461 1465 doi 10 1002 cber 19971301017 Smith Michael B March Jerry 2007 Advanced Organic Chemistry Reactions Mechanisms and Structure 6th ed New York Wiley Interscience ISBN 978 0 471 72091 1 K Izutsu 1990 Acid Base Dissociation Constants in Dipolar Aprotic Solvents Vol 35 Blackwell Scientific Publications External links edit nbsp Media related to Sodium phenoxide at Wikimedia Commons Retrieved from https en wikipedia org w index php title Sodium phenoxide amp oldid 1177810390, wikipedia, wiki, book, books, library,
