فينولات الصوديوم

فينولات الصوديوم
الأسماء
	اسم أيوپاك المفضل Sodium phenoxide
	أسماء أخرى Sodium phenolate
المُعرِّفات
رقم CAS
3D model (JSmol)	Interactive image;
ChemSpider	8420;
ECHA InfoCard	100.004.862
PubChem CID	4445035;
UNII	4NC0T56V35 ;
CompTox Dashboard (EPA)	DTXSID4027072 ;
	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;
الخصائص
الصيغة الجزيئية	C6H5NaO
كتلة مولية	116.09 g/mol
المظهر	White solid
المخاطر
خطر رئيسي	Harmful, Corrosive
نقطة الوميض	Non-flammable
درجة حرارة; الاشتعال الذاتي	Non-flammable
	ما لم يُذكر غير ذلك، البيانات المعطاة للمواد في حالاتهم العيارية (عند 25 °س [77 °ف]، 100 kPa).
	مراجع الجدول

فينولات الصوديوم وهو ملح الصوديوم للفينول، صيغته 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.

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

التحضير

يحضر فينولات الصوديوم من تفاعل الفينول مع هيدروكسيد الصوديوم.^[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 → C₆H₅ONa + Na₂SO₃

This route once was the principal industrial route to phenol.^{[بحاجة لمصدر]}

الاستخدامات

يستخدم مركب فينولات الصوديوم من أجل تحضير حمض الساليسيليك عن طريق تفاعل كولبة-شميت. يجري التفاعل بتسخين المركب تحت الضغط بوجود غاز ثنائي أكسيد الكربون فينتج لدينا مركب ساليسيلات الصوديوم، الذي يعالج بحمض الكبريتيك

البنية

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.

التفاعلات

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.

المراجع

^ 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.
^ ^أ ^ب "γ-Phenoxypropyl Bromide". Org. Synth. 9: 72. 1929. doi:10.15227/orgsyn.009.0072. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
^ 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
^ قالب:March6th
^ K. Izutsu (1990). Acid-Base Dissociation Constants in Dipolar Aprotic Solvents. Vol. 35. Blackwell Scientific Publications.

هذه بذرة مقالة عن الكيمياء تحتاج للنمو والتحسين، ساهم في إثرائها بالمشاركة في تحريرها.

الكلمات الدالة:

[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.

[Speed-2] أ ^ب "γ-Phenoxypropyl Bromide". Org. Synth. 9: 72. 1929. doi:10.15227/orgsyn.009.0072. {{cite journal}}: Cite uses deprecated parameter |authors= (help)

[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] قالب:March6th

[6] K. Izutsu (1990). Acid-Base Dissociation Constants in Dipolar Aprotic Solvents. Vol. 35. Blackwell Scientific Publications.

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