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环戊二烯基钠

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环戊二烯基钠
别名 烯环钠
识别
CAS号 4984-82-1  ✓
PubChem 78681
ChemSpider 71032
SMILES
InChI
EINECS 225-636-8
性质
化学式 C5H5Na
摩尔质量 88.08 g·mol−1
外观 无色固体
溶解性 分解
溶解性 THF
危险性
主要危害 易燃
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

环戊二烯基钠是一种有机钠化合物,又称烯环钠,化学式为NaC5H5。通常简称为NaCp或CpNa,其中Cp环戊二烯阴离子。在配位化学中,Cp也作为环戊二烯基配体的缩写。[1]环戊二烯基钠是无色固体,但样本会因为氧化而呈粉红色。[2]

制备

市售有环戊二烯基钠的THF的溶液。可通过用处理环戊二烯制备:[3]

2 Na + 2 C5H6 → 2 NaC5H5 + H2

通常是在双环戊二烯中加热钠至熔融态以进行反应[2]。以前的常见做法是用“钠丝”或“钠砂”,这可通过二甲苯熔融回流钠,同时快速搅拌来制得这种细分散体的形式[4][5]。使用氢化钠更易制备:[6]

NaH + C5H6 → NaC5H5 + H2

早期的实验使用格氏试剂作为反应物。环戊二烯pKa为15,因此可以被许多试剂去质子化。

NaCp的性质很大程度上取决于它所处的介质。在一些合成路线中,该试剂通常表示为Na+C5H5的盐形式。少见的无溶剂结晶NaCp是一个像防滑垫式的夹心型配合物,含有夹在μ-η55-C5H5配体中交替的Na+中心构成的无限链条[7]。在溶剂中,NaCp是高度溶剂化的,特别是碱金属加合物Na(tmeda)Cp更能增加区分度[8]

应用

环戊二烯基钠是一种常见制备茂金属的试剂。如二茂铁[4]二氯二茂锆[9]的制备:

2 NaC5H5 + FeCl2 → Fe(C5H5)2 + 2 NaCl
ZrCl4(thf)2 + 2 NaCp → Cp2ZrCl2 + 2 NaCl + 2 THF

参考

  1. ^ International Union of Pure and Applied Chemistry (2005). Nomenclature of Inorganic Chemistry (IUPAC Recommendations 2005). Cambridge (UK): RSC–IUPAC. ISBN 0-85404-438-8. pp. 262 (PDF页面存档备份,存于互联网档案馆))
  2. ^ 2.0 2.1 Tarun K. Panda, Michael T. Gamer, Peter W. Roesky. An Improved Synthesis of Sodium and Potassium Cyclopentadienide. Organometallics. 2003, 22: 877–878 [2015-12-04]. doi:10.1021/om0207865. (原始内容存档于2021-07-13). 
  3. ^ Cotton, F. Albert; Wilkinson, Geoffrey, Advanced Inorganic Chemistry 5th, New York: Wiley-Interscience: 139, 1988, ISBN 0-471-84997-9 
  4. ^ 4.0 4.1 Geoffrey Wilkinson (1963). "Ferrocene". Org. Synth.; Coll. Vol. 4: 473. 
  5. ^ Partridge, John J.; Chadha, Naresh K.; Uskokovic, Milan R. (1990). "An asymmetric hydroboration of 5-substituted cyclopentadienes: synthesis of methyl (1R,5R)-5-hydroxy-2-cyclopentene-1-acetate". Org. Synth.; Coll. Vol. 7: 339. 
  6. ^ Girolami, G. S.; Rauchfuss, T. B. and Angelici, R. J. Synthesis and Technique in Inorganic Chemistry. CA: University Science Books: Mill Valley. 1999. ISBN 0935702482. 
  7. ^ Robert E. Dinnebier, Ulrich Behrens, and Falk Olbrich. Solid State Structures of Cyclopentadienyllithium, -sodium, and -potassium. Determination by High-Resolution Powder Diffraction. Organometallics. 1997, 16: 3855–3858. doi:10.1021/om9700122. 
  8. ^ Elschenbroich, C. Organometallics. Wiley-VCH: Weinheim. 2006. ISBN 978-3-527-29390-2. 
  9. ^ Geoffrey Wilkinson; Birmingham, J. G. Bis-cyclopentadienyl Compounds of Ti, Zr, V, Nb and Ta. J. Am. Chem. Soc. 1954, 76 (17): 4281–84. doi:10.1021/ja01646a008. 
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环戊二烯基钠
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