酚盐

酚盐是酚类有机物的羟基氢被金属离子取代得到的化合物，通式为ArOM（Ar为芳基）。

制备

酚盐可由酚和碱金属氢氧化物反应制得。^[1]

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

其它碱，如金属氢化物、烷基金属、三甲基硅基氨基化物^[2]^[3]也可用作酚类的脱质子试剂制备酚盐。

酸性较强的酚可以直接和金属化合物反应，生成相应的酚。例如苦味酸（2,4,6-三硝基苯酚）和碳酸铅或乙酸铅反应，可以得到苦味酸铅。^[4]

性质

Mⁿ⁺和OAr⁻形成配阴离子的结构示意图。（原子颜色：灰色碳，红色氧，深蓝色金属）

碱金属酚盐可以作为亲核试剂和卤代烃发生威廉姆逊反应，例如：^[5]

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

苯酚钠或苯酚钾在加热、加压下还能发生科尔贝－施密特反应，这一反应在工业上用于制备水杨酸：^[6]

过渡金属和芳氧基阴离子可以形成酚盐配合物，例如(Ph₄P)₂[Cu(OAr)₄]中含有[Cu(OAr)₄]²⁻离子。^[7]铁盐可以和酚发生显色反应，其颜色也来自形成的配合物。^[8]

参考文献

^ 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.

参见

醇盐

[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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