酚鹽

酚鹽是酚類有機物的羥基氫被金屬離子取代得到的化合物，通式為ArOM（Ar為芳基）。

製備

酚鹽可由酚和鹼金屬氫氧化物反應製得。^[1]

\mathrm {ArOH\ +\ MOH\longrightarrow \ ArOM\ +\ H_{2}O}

其它鹼，如金屬氫化物、烷基金屬、三甲基矽基氨基化物^[2]^[3]也可用作酚類的脫質子試劑製備酚鹽。

酸性較強的酚可以直接和金屬化合物反應，生成相應的酚。例如苦味酸（2,4,6-三硝基苯酚）和碳酸鉛或乙酸鉛反應，可以得到苦味酸鉛。^[4]

性質

Mⁿ⁺和OAr⁻形成配陰離子的結構示意圖。（原子顏色：灰色碳，紅色氧，深藍色金屬）

鹼金屬酚鹽可以作為親核試劑和鹵代烴發生威廉姆遜反應，例如：^[5]

\mathrm {C_{6}H_{5}{-}ONa\ +\ CH_{3}{-}I\longrightarrow \ C_{6}H_{5}{-}O{-}CH_{3}\ +\ NaI}

苯酚鈉或苯酚鉀在加熱、加壓下還能發生科爾貝－施密特反應，這一反應在工業上用於製備水楊酸：^[6]

過渡金屬和芳氧基陰離子可以形成酚鹽配合物，例如(Ph₄P)₂[Cu(OAr)₄]中含有[Cu(OAr)₄]²⁻離子。^[7]鐵鹽可以和酚發生顯色反應，其顏色也來自形成的配合物。^[8]

參考文獻

^ Hans-Dieter Jakubke, Ruth Karcher (Koordinatoren): Lexikon der Chemie in drei Bänden, Spektrum Verlag, Heidelberg, Band 3, 1999, pp. 14. ISBN 3-8274-0381-2
^ Huang, Yong; Wang, Wei; Lin, Chu-Chieh; Blake, Matthew P.; Clark, Lawrence; Schwarz, Andrew D.; Mountford, Philip. Potassium, zinc, and magnesium complexes of a bulky OOO-tridentate bis(phenolate) ligand: synthesis, structures, and studies of cyclic ester polymerisation. Dalton Transactions. 2013, 42 (25): 9313. ISSN 1477-9226. doi:10.1039/c3dt50135c.
^ Binda, Pascal I.; Delbridge, Ewan E.; Dugah, Divine T.; Skelton, Brian W.; White, Allan H. Synthesis and Structural Characterization of Some Potassium Complexes of Some Bis(phenolate) Ligands and Some Novel Heterobimetallic Binuclear Arrays Formed with Trivalent Lanthanoid Ions. Zeitschrift für anorganische und allgemeine Chemie. 2008, 634 (2): 325–334. ISSN 0044-2313. doi:10.1002/zaac.200700442.
^ Matsukawa M, Matsunaga T, Yoshida M, et al. Synthesis and properties of lead picrates. Science and Technology of Energetic Materials, 2004, 65(1): 7-13.
^ Hans Beyer und Wolfgang Walter: Organische Chemie, S. Hirzel Verlag, Stuttgart, 1984, pp. 463–464, ISBN 3-7776-0406-2.
^ Lindsey, Alan S.; Jeskey, Harold. The Kolbe-Schmitt Reaction. Chemical Reviews. 1957, 57 (4): 583–620. ISSN 0009-2665. doi:10.1021/cr50016a001.
^ Buzzeo, Marisa C.; Iqbal, Amber H.; Long, Charli M.; Millar, David; Patel, Sonal; Pellow, Matthew A.; Saddoughi, Sahar A.; Smenton, Abigail L.; Turner, John F. C.; Wadhawan, Jay D.; Compton, Richard G.; Golen, James A.; Rheingold, Arnold L.; Doerrer, Linda H. Homoleptic Cobalt and Copper Phenolate A₂[M(OAr)₄] Compounds: The Effect of Phenoxide Fluorination. Inorganic Chemistry. 2004, 43 (24): 7709–7725. ISSN 0020-1669. doi:10.1021/ic0493954.
^ Gore, P.H.; Newman, P.J. Quantitative aspects of the colour reaction between Iron(III) and phenols. Analytica Chimica Acta. 1964, 31: 111–120. ISSN 0003-2670. doi:10.1016/S0003-2670(00)88791-7.

參見

醇鹽

[1] Hans-Dieter Jakubke, Ruth Karcher (Koordinatoren): Lexikon der Chemie in drei Bänden, Spektrum Verlag, Heidelberg, Band 3, 1999, pp. 14. ISBN 3-8274-0381-2

[2] Huang, Yong; Wang, Wei; Lin, Chu-Chieh; Blake, Matthew P.; Clark, Lawrence; Schwarz, Andrew D.; Mountford, Philip. Potassium, zinc, and magnesium complexes of a bulky OOO-tridentate bis(phenolate) ligand: synthesis, structures, and studies of cyclic ester polymerisation. Dalton Transactions. 2013, 42 (25): 9313. ISSN 1477-9226. doi:10.1039/c3dt50135c.

[3] Binda, Pascal I.; Delbridge, Ewan E.; Dugah, Divine T.; Skelton, Brian W.; White, Allan H. Synthesis and Structural Characterization of Some Potassium Complexes of Some Bis(phenolate) Ligands and Some Novel Heterobimetallic Binuclear Arrays Formed with Trivalent Lanthanoid Ions. Zeitschrift für anorganische und allgemeine Chemie. 2008, 634 (2): 325–334. ISSN 0044-2313. doi:10.1002/zaac.200700442.

[4] Matsukawa M, Matsunaga T, Yoshida M, et al. Synthesis and properties of lead picrates. Science and Technology of Energetic Materials, 2004, 65(1): 7-13.

[5] Hans Beyer und Wolfgang Walter: Organische Chemie, S. Hirzel Verlag, Stuttgart, 1984, pp. 463–464, ISBN 3-7776-0406-2.

[6] Lindsey, Alan S.; Jeskey, Harold. The Kolbe-Schmitt Reaction. Chemical Reviews. 1957, 57 (4): 583–620. ISSN 0009-2665. doi:10.1021/cr50016a001.

[7] Buzzeo, Marisa C.; Iqbal, Amber H.; Long, Charli M.; Millar, David; Patel, Sonal; Pellow, Matthew A.; Saddoughi, Sahar A.; Smenton, Abigail L.; Turner, John F. C.; Wadhawan, Jay D.; Compton, Richard G.; Golen, James A.; Rheingold, Arnold L.; Doerrer, Linda H. Homoleptic Cobalt and Copper Phenolate A₂[M(OAr)₄] Compounds: The Effect of Phenoxide Fluorination. Inorganic Chemistry. 2004, 43 (24): 7709–7725. ISSN 0020-1669. doi:10.1021/ic0493954.

[8] Gore, P.H.; Newman, P.J. Quantitative aspects of the colour reaction between Iron(III) and phenols. Analytica Chimica Acta. 1964, 31: 111–120. ISSN 0003-2670. doi:10.1016/S0003-2670(00)88791-7.

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