硫酚盐

硫酚盐是硫酚失去巯基的氢后和金属离子、金属簇或非金属离子形成的盐。当芳环上连接多个巯基时，它们脱质子后可以与金属形成配位聚合物或金属有机框架材料。

因可以形成多种具有高导电性的材料（如[Cu6(C6S6)]n等）而倍受研究者关注。Xiangzhi Meng; et al. Tunable Thiolate Coordination Networks on Metal Surfaces. ChemNanoMat, 2020. 6 (10): 1479-1484. .
合成及反应
由于硫酚具有较强的酸性，它的盐可由相应的碱在乙醇甚至水中反应得到：Dillon M. Love; et al. Amine Induced Retardation of the Radical-Mediated Thiol–Ene Reaction via the Formation of Metastable Disulfide Radical Anions. J. Org. Chem. 2018, 83, 5, 2912–2919. .Pooja Dubey; et al. Sonogashira Coupling (Cu/Amine-Free) of ArBr/Cl in Aerobic Condition and N-Benzylation of Aniline with Benzyl Alcohol Catalyzed by Complexes of Pd(II) with Sulfated/Selenated NHCs. ChemistrySelect (2020), 5(10), 2925-2934. .
 300px

二价铜（以及三价金、四价铂等）可以将硫酚氧化为二芳基二硫化物，并形成CuISAr，若要制得纯净的硫酚亚铜，需要用合适的溶剂将二硫化物洗去。Michael E. Peach. Preparation and thermal decomposition of some metal thiophenolates. J. Inorg. Nucl. Chem, 1979. 41 (9), 1390–1392. .

在钯配合物催化下，硫酚盐（如硫酚钠）可以和卤代烃反应，生成相应的芳基硫醚。Thomas Scattolin; et al. Site-Selective C−S Bond Formation at C−Br over C−OTf and C−Cl Enabled by an Air-Stable, Easily Recoverable, and Recyclable Palladium(I) Catalyst. Angew Chem Int Ed. 2018. 57 (38). 12425-12429. .

硫酚盐列表
已被报道的硫酚盐参见下表：
 化合物  化学式  外观  熔点（°C）  空间群  注释  参考文献 苯硫酚亚铜  CuSC6H5  黄绿色  252-254 (dec)    [a] 苯硫酚银  AgSC6H5  黄色  312-315    [a] 4-氟苯硫酚银  [AgSC6H4F]n  白色   P21/n  无光致发光现象  Saly Hawila; et al. Tuning the 1D–2D dimensionality upon ligand exchange in silver thiolate coordination polymers with photoemission switching. J. Mater. Chem. B, 2023,11, 3979-3984. . ... the lamellar 1 and 2, which are non-luminescent 4-氯苯硫酚银  [AgSC6H4Cl]n  白色    Iba2  无光致发光现象   苯硫酚亚金  AuSC6H5  浅黄色  198-203 (dec)    [a] 二苯硫基金(I)酸四丁基铵  [(C4H9)4N][Au(SC6H5)2]  无色  66.5-67.5   λem(max)=501 nm（λex=350 nm） Seiji Watase; et al. Solid-state luminescence and crystal structures of novel gold(I) benzenethiolate complexes. J. Chem. Soc., Dalton Trans., 2000, 3585-3590. . 二十(4-叔丁基苯硫基)二十八金  Au28(tC4H9C6H4S)20  棕色   P   Chenjie Zeng; et al. Chiral Structure of Thiolate-Protected 28-Gold-Atom Nanocluster Determined by X-ray Crystallography. J. Am. Chem. Soc. 2013, 135, 27, 10011–10013. . 二十八(4-叔丁基苯硫基)四十四金  Au44(tC4H9C6H4S)28  黑色   C2/c   Chenjie Zeng; et al. Gold Quantum Boxes: On the Periodicities and the Quantum Confinement in the Au28, Au36, Au44, and Au52 Magic Series. J. Am. Chem. Soc. 2016, 138, 12, 3950–3953. . 五十二(4-叔丁基苯硫基)一百三十三金  Au133(tC4H9C6H4S)52  暗紫色针状   P（170 K）   Chenjie Zeng; et al. Structural patterns at all scales in a nonmetallic chiral Au133(SR)52 nanoparticle. Sci. Adv, 2015. 1 (2). . 苯硫酚三(4-三氟甲基苯基)膦亚金  (F3CC6H4)3PAuSC6H5  黄色针状   P  Keiko Nunokawa; et al. Substituent effects on aurophilicity and π–π interaction in crystals of arylphosphine–Au(I) derivatives. Synthesis and X-ray structural studies of compounds (CX3C6H4)3P-Au-X and {(CF3)2C6H3}3P-Au-X. Inorganic Chimica Acta, 2001. 322 (1-2). 56-64. . 4-吡啶硫基(三苯基膦)金(I)二聚体  [(C5H4NS)Au(P(C6H5)3)]2  浅黄色   P   苯硫酚亚铊  TlSC6H5  浅黄色  255-260 (dec)    [a] 苯硫酚锌  Zn(SC6H5)2  白色  222-227    [a] 苯硫酚镉  Cd(SC6H5)2  白色  320-325  P212121   [a]Ian G. Dance; et al. The different nonmolecular polyadamantanoid crystal structures of cadmium benzenethiolate and 4-methylbenzenethiolate. Analogies with microporous aluminosilicate frameworks. Inorg. Chem. 1987, 26, 24, 4057–4064. . 4-甲基苯硫酚镉  Cd(SC6H4CH3)2   285 (dec)  P21/c    苯硫酚汞  Hg(SC6H5)2  白色  150-154    [a] 4-叔丁基苯硫酚汞  Hg(SC6H4tC4H9)2  白色   P   Jonathan G. Melnick; et al. Synthesis, Structure, and Reactivity of Two-Coordinate Mercury Alkyl Compounds with Sulfur Ligands: Relevance to Mercury Detoxification. Inorg. Chem. 2009, 48, 14, 6763–6772. . 苯硫酚锡  Sn(SC6H5)2  浅黄色  153-154 (dec)    [a] 苯硫酚铅  Pb(SC6H5)2  黄色  190-195    [a] 苯硫酚铁(III)  Fe(SC6H5)3  深棕色        苯硫酚钴  Co(SC6H5)2  棕绿色  290-295    [a] 苯硫酚镍  Ni(SC6H5)2  红棕色  310-315 (dec)    [a] 苯硫酚钯  Pd(SC6H5)2  红棕色  320    [a] 苯硫酚亚铂  Pt(SC6H5)2  亮黄色  320    [a] 苯硫酚钼(III)  [Mo(SC6H5)3]n  深红色    Pnmn  Ulrich Berger; Joachim Strähle. Polymere Thiolatokomplexe [M(SPh)3]∞ der Metalle Molybdän, Wolfram, Eisen und Ruthenium mit linearen Metallketten. Synthese und Struktur von (OC)3Fe(SPh)3Fe(SPh)3Fe(CO)3·2(CH3)2CO. Zeitschrift fur Anorganische und Allgemeine Chemie, 1984, 516, 19, . 苯硫酚钌(III)  [Ru(SC6H5)3]n  暗绿色    Pnmn    苯硫酚钨(III)  [W(SC6H5)3]n  棕黑色    Pnmn    苯硫酚铋  Bi(SC6H5)3  橙色  95-97 (dec)    [a]
注释：[a] 文献

参考文献

*