Sodium phenoxide-Wikipedia

Sodium phenoxide

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Sodium phenoxide

Structural formula of sodium phenoxide.svg

Names

Preferred IUPAC name

Sodium phenoxide

[1]

Other names

Sodium phenolate
Identifiers

CAS Number

  • 139-02-6 checkY
3D model (

JSmol

)

  • Interactive image

ChemSpider

  • 8420

ECHA InfoCard

100.004.862

Edit this at Wikidata

PubChem

CID

  • 4445035

UNII

  • 4NC0T56V35

     checkY

CompTox Dashboard

(EPA)

  • DTXSID4027072

    Edit this at Wikidata

InChI

  • InChI=1S/C6H6O.Na/c7-6-4-2-1-3-5-6;/h1-5,7H;/q;+1/p-1
    Key: NESLWCLHZZISNB-UHFFFAOYSA-M
  • InChI=1/C6H6O.Na/c7-6-4-2-1-3-5-6;/h1-5,7H;/q;+1/p-1
    Key: NESLWCLHZZISNB-REWHXWOFAP

SMILES

  • [Na+].[O-]c1ccccc1
Properties

Chemical formula

C6H5NaO

Molar mass

116.09 g/mol
Appearance White solid
Hazards
Main

hazards

Harmful, Corrosive

Flash point

Nonflammable

Autoignition
temperature

Nonflammable
Except where otherwise noted, data are given for materials in their

standard state

(at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

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

.

Xem thêm: Thăm, tặng quà, chúc Tết các đơn vị lực lượng vũ trang trên địa bàn

Synthesis and structure[

edit

]

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

Structure[

edit

]

Like other sodium

alkoxides

, solid sodium phenolate 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]

Sodium phenoxide can be produced by the “alkaline fusion” of

benzenesulfonic acid

, whereby the sulfonate groups are displaced by hydroxide:

C6H5SO3Na + 2 NaOH → C6H5ONa + Na2SO3

This route once was the principal industrial route to phenol.

Subunit of the structure of solvent-free sodium phenoxide, illustrating the binding of phenoxide to sodium through both the arene and the oxygen.

Xem thêm: Hoán vị-Tổ hợp-Chỉnh hợp-O2 Education

Reactions[

edit

]

Sodium phenoxide is a moderately strong base. Acidification gives phenol:

[5]

PhOH ⇌ PhO + H+          (K = 10−10)

Alkylation affords phenyl ethers:

[2]

NaOC6H5 + RBr → ROC6H5 + NaBr

The conversion is an extension of the

Williamson ether synthesis

. With acylating agents, one obtains 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.

The Kolbe–Schmitt reaction.

Xem thêm: Phương trình bậc hai một ẩn: Lý thuyết và cách giải phương trình

References[

edit

]

  1. ^

    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

    .

  2. ^

    a

    b

    C. S. Marvel, A. L. Tanenbaum (1929). “γ-Phenoxypropyl Bromide”. Org. Synth. 9: 72.

    doi

    :

    10.15227/orgsyn.009.0072

    .CS1 maint: uses authors parameter (

    link

    )

  3. ^

    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

    .

  4. ^

    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

  5. ^

    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

External links[

edit

]

Media related to

Sodium phenoxide

at Wikimedia Commons

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