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十甲基二茂铁

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十甲基二茂铁
IUPAC名
Decamethylferrocene
识别
CAS号 12126-50-0  ✓
PubChem 5148079
ChemSpider 4321548
SMILES
InChI
InChIKey SEYZDJPFVVXSRB-UHFFFAOYAP
性质
化学式 C20H30Fe
摩尔质量 326.3 g·mol−1
外观 黄色晶体[1]
熔点 291-295 °C(564-568 K)([1]
升华条件 413 K, 5.3 Pa[2]
升华条件 413 K, 5.3 Pa[2]
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

十甲基二茂铁,又称双(五甲基环五二烯)铁(II),是一种有机化合物,化学式 Fe(C
5
(CH
3
)
5
)
2
或C
20
H
30
Fe。它是一种夹心配合物,由亚铁离子(Fe2+)和两个五甲基环戊二烯阴离子(Cp*-或(CH
3
)
5
C
5
)组成。它是二茂铁的衍生物,由甲基取代所有的原子而成。十甲基二茂铁有时简写为DmFc[3] Me
10
Fc [4]或FeCp*2[5]

十甲基二茂铁是一种黄色晶体,是一种还原剂Fe(II)中心可以被轻易氧化成Fe(III),产生一价正离子十甲基二茂铁(III)阳离子,甚至更高的氧化态。[6]

制备

十甲基二茂铁可以由五甲基环戊二烯衍生物和氯化亚铁反应而成:[7]

2 Li(C5Me5) + FeCl2 → Fe(C5Me5)2 + 2 LiCl

产物可以通过升华纯化。铁-碳平均距离约为 2.050 Å。它的结构已被X射线晶体学确认。[8]

反应

类似二茂铁,十甲基二茂铁的 Fe(II) 容易被氧化成 Fe(III)。由于十个甲基的诱导效应,十甲基二茂铁的还原性比二茂铁强。氧气在十甲基二茂铁的酸性溶液中会被还原成过氧化氢[9]

使用强氧化剂(例如SbF
5
或AsF
5
的SO
2
溶液,或是XeF+/Sb
2
F
11
的HF/SbF
5
溶液)氧化十甲基二茂铁可以得到稳定的十甲基二茂铁(IV)双阳离子。在它的Sb
2
F
11
盐中,两个Cp环是平行的。相比之下,两个Cp环在SbF
6
盐中有17°的倾斜。[5]

参考资料

  1. ^ 1.0 1.1 King, R. B.; Bisnette, M. B. Organometallic Chemistry of the Transition Metals XXI. Some π-pentamethylcyclopentadienyl Derivatives of Various Transition Metals. J. Organomet. Chem. 1967, 8 (2): 287–297. doi:10.1016/S0022-328X(00)91042-8. 
  2. ^ Connelly, N.; Geiger, W. E. Chemical Redox Agents for Organometallic Chemistry. Chem. Rev. 1996, 96 (2): 877–910. PMID 11848774. doi:10.1021/cr940053x. 
  3. ^ Torriero, Angel A.J. Characterization of decamethylferrocene and ferrocene in ionic liquids: argon and vacuum effect on their electrochemical properties. Electrochimica Acta. 2014, 137: 235–244. doi:10.1016/j.electacta.2014.06.005. 
  4. ^ Noviandri, Indra; Brown, Kylie N.; Fleming, Douglas S.; Gulyas, Peter T.; Lay, Peter A.; Masters, Anthony F.; Phillips, Leonidas. The Decamethylferrocenium/Decamethylferrocene Redox Couple: A Superior Redox Standard to the Ferrocenium/Ferrocene Redox Couple for Studying Solvent Effects on the Thermodynamics of Electron Transfer. The Journal of Physical Chemistry B. 1 August 1999, 103 (32): 6713–6722. ISSN 1520-6106. doi:10.1021/jp991381+. 
  5. ^ 5.0 5.1 Malischewski, M.; Adelhardt, M.; Sutter, J.; Meyer, K.; Seppelt, K. Isolation and structural and electronic characterization of salts of the decamethylferrocene dication. Science. 2016, 353 (6300): 678–682. Bibcode:2016Sci...353..678M. PMID 27516596. doi:10.1126/science.aaf6362. 
  6. ^ M. Malischewski, M. Adelhardt, J. Sutter, K. Meyer, K. Seppelt. Isolation and structural and electronic characterization of salts of the decamethylferrocene dication. Science. 2016-08-12, 353 (6300): 678–682 [2021-07-20]. ISSN 0036-8075. doi:10.1126/science.aaf6362 (英语). 
  7. ^ R.B. King, M.B. Bisnette: Organometallic chemistry of the transition metals XXI. Some π-pentamethylcyclopentadienyl derivatives of various transition metals. In: Journal of Organometallic Chemistry. 8, 1967, S. 287, doi:10.1016/S0022-328X(00)91042-8.
  8. ^ Freyberg, Derek P.; Robbins, John L.; Raymond, Kenneth N.; Smart, James C. Crystal and molecular structures of decamethylmanganocene and decamethylferrocene. Static Jahn-Teller distortion in a metallocene. J. Am. Chem. Soc. 1979, 101 (4): 892–897. doi:10.1021/ja00498a017. 
  9. ^ Su, Bin; Hatay, Imren; Ge, Pei Yu; Mendez, Manuel; Corminboeuf, Clemence; Samec, Zdenek; Ersoz, Mustafa; Girault, Hubert H. Oxygen and proton reduction by decamethylferrocene in non-aqueous acidic media. Chem. Commun. 2010, 46 (17): 2918–2919 [2021-07-18]. PMID 20386822. doi:10.1039/B926963K. (原始内容存档于2020-06-12). 
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十甲基二茂铁
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