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Variables generated for this change
| Variable | Value |
|---|---|
Edit count of the user (user_editcount) | null |
Name of the user account (user_name) | '79.119.58.214' |
Age of the user account (user_age) | 0 |
Groups (including implicit) the user is in (user_groups) | [
0 => '*'
] |
Global groups that the user is in (global_user_groups) | [] |
Whether or not a user is editing through the mobile interface (user_mobile) | true |
Page ID (page_id) | 13224606 |
Page namespace (page_namespace) | 0 |
Page title without namespace (page_title) | 'Sodium phenoxide' |
Full page title (page_prefixedtitle) | 'Sodium phenoxide' |
Last ten users to contribute to the page (page_recent_contributors) | [
0 => 'The chemistds',
1 => 'DePiep',
2 => 'Smokefoot',
3 => 'ChemNerd',
4 => 'Rifleman 82',
5 => 'Cacycle'
] |
Action (action) | 'edit' |
Edit summary/reason (summary) | 'Fixed typo' |
Whether or not the edit is marked as minor (no longer in use) (minor_edit) | false |
Old page wikitext, before the edit (old_wikitext) | '{{Chembox
| ImageFile = Fenolan sodu.svg
| ImageSize = 75px
| ImageAlt =
| IUPACName =
| OtherNames = Sodium phenylate
|Section1={{Chembox Identifiers
| CASNo = 139-02-6
| PubChem = 4445035
| ChemSpiderID = 8420
| SMILES = c1ccc(cc1)[O-].[Na+]
| InChI = 1/C6H6O.Na/c7-6-4-2-1-3-5-6;/h1-5,7H;/q;+1/p-1
| InChIKey = NESLWCLHZZISNB-REWHXWOFAP
| StdInChI = 1S/C6H6O.Na/c7-6-4-2-1-3-5-6;/h1-5,7H;/q;+1/p-1
| StdInChIKey = NESLWCLHZZISNB-UHFFFAOYSA-M }}
|Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>5</sub>NaO
| MolarMass = 116.09 g/mol
| Appearance = White solid
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
'''Sodium phenoxide''' is an [[organic compound]] with the formula NaOC<sub>6</sub>H<sub>5</sub>. This white solid is the [[conjugate base]] of [[phenol]]. It is used as a precursor to many other organic compounds, such as aryl [[ether]]s.
==Synthesis and structure==
Most commonly, solutions of sodium phenoxide are produced by treating phenol with sodium hydroxide.<ref name=Speed>C. S. Marvel and A. L. Tanenbaum "γ-Phenoxypropyl Bromide" Org. Synth. 1929, vol. 9, pp. 72.</ref> Anhydrous derivatives can be prepared from phenol and sodium:
:Na + HOC<sub>6</sub>H<sub>5</sub> → NaOC<sub>6</sub>H<sub>5</sub> + 1/2 H<sub>2</sub>
Like other sodium [[alkoxide]]s, crystalline sodium phenolate adopts a complex structures 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 [NaOPh]<sub>4</sub>([[HMPA]])<sub>4</sub>.<ref>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}}</ref>
==Reactions==
Sodium phenoxide is a moderately strong base. At low pH's gives phenol:<ref>{{March6th}}</ref>
:PhOH {{unicode|⇌}} PhO<sup>−</sup> + H<sup>+</sup> (K = 10<sup>−10</sup>)
Sodium phenoxide can be used to prepare phenyl ethers and metal phenolates:<ref name=Speed/>
:NaOC<sub>6</sub>H<sub>5</sub> + RBr → ROC<sub>6</sub>H<sub>5</sub> + NaBr
==References==
<references />
==External links==
{{commons category inline}}
[[Category:Phenols]]
[[Category:Sodium compounds]]' |
New page wikitext, after the edit (new_wikitext) | '{{Chembox
| ImageFile = Fenolan sodu.svg
| ImageSize = 75px
| ImageAlt =
| IUPACName =
| OtherNames = Sodium phenolate
|Section1={{Chembox Identifiers
| CASNo = 139-02-6
| PubChem = 4445035
| ChemSpiderID = 8420
| SMILES = c1ccc(cc1)[O-].[Na+]
| InChI = 1/C6H6O.Na/c7-6-4-2-1-3-5-6;/h1-5,7H;/q;+1/p-1
| InChIKey = NESLWCLHZZISNB-REWHXWOFAP
| StdInChI = 1S/C6H6O.Na/c7-6-4-2-1-3-5-6;/h1-5,7H;/q;+1/p-1
| StdInChIKey = NESLWCLHZZISNB-UHFFFAOYSA-M }}
|Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>5</sub>NaO
| MolarMass = 116.09 g/mol
| Appearance = White solid
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
'''Sodium phenoxide''' is an [[organic compound]] with the formula NaOC<sub>6</sub>H<sub>5</sub>. This white solid is the [[conjugate base]] of [[phenol]]. It is used as a precursor to many other organic compounds, such as aryl [[ether]]s.
==Synthesis and structure==
Most commonly, solutions of sodium phenoxide are produced by treating phenol with sodium hydroxide.<ref name=Speed>C. S. Marvel and A. L. Tanenbaum "γ-Phenoxypropyl Bromide" Org. Synth. 1929, vol. 9, pp. 72.</ref> Anhydrous derivatives can be prepared from phenol and sodium:
:Na + HOC<sub>6</sub>H<sub>5</sub> → NaOC<sub>6</sub>H<sub>5</sub> + 1/2 H<sub>2</sub>
Like other sodium [[alkoxide]]s, crystalline sodium phenolate adopts a complex structures 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 [NaOPh]<sub>4</sub>([[HMPA]])<sub>4</sub>.<ref>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}}</ref>
==Reactions==
Sodium phenoxide is a moderately strong base. At low pH's gives phenol:<ref>{{March6th}}</ref>
:PhOH {{unicode|⇌}} PhO<sup>−</sup> + H<sup>+</sup> (K = 10<sup>−10</sup>)
Sodium phenoxide can be used to prepare phenyl ethers and metal phenolates:<ref name=Speed/>
:NaOC<sub>6</sub>H<sub>5</sub> + RBr → ROC<sub>6</sub>H<sub>5</sub> + NaBr
==References==
<references />
==External links==
{{commons category inline}}
[[Category:Phenols]]
[[Category:Sodium compounds]]' |
Unified diff of changes made by edit (edit_diff) | '@@ -4,5 +4,5 @@
| ImageAlt =
| IUPACName =
-| OtherNames = Sodium phenylate
+| OtherNames = Sodium phenolate
|Section1={{Chembox Identifiers
| CASNo = 139-02-6
' |
New page size (new_size) | 2560 |
Old page size (old_size) | 2560 |
Size change in edit (edit_delta) | 0 |
Lines added in edit (added_lines) | [
0 => '| OtherNames = Sodium phenolate'
] |
Lines removed in edit (removed_lines) | [
0 => '| OtherNames = Sodium phenylate'
] |
Whether or not the change was made through a Tor exit node (tor_exit_node) | 0 |
Unix timestamp of change (timestamp) | 1450277332 |