Phenylsilver

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Phenylsilver
Phenylsilver Polymer.svg
Identifiers
3D model (JSmol)
PubChem CID
  • InChI=1S/C6H5.Ag/c1-2-4-6-5-3-1;/h1-5H;/q-1;+1
    Key: APUVPJCKRFJPND-UHFFFAOYSA-N
  • c1ccccc1[Ag]
Properties
C6H5Ag
Molar mass 184.974 g·mol−1
Appearancewhite solid [1]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Phenylsilver is an organosilver compound with the chemical formula C 6 H 5 Ag . It is a white solid. The structure is a one-dimensional coordination polymer of silver(I) tetrads. [2]

Contents

Synthesis

It can be produced by treating silver nitrate with trialkylphenyltin (or trialkylphenyllead at −10 °C). In the presence of excess silver nitrate, the reaction produces the bright yellow complex C6H5Ag·2AgNO3. [1] Phenylsilver can also be produced by treating silver nitrate with diphenylzinc in a 1:2 molar ratio and 0 °C. If the molar ratio is 1:1, it will produce orange C6H5Ag·2AgNO3. [3] Earlier syntheses using phenyl magnesium bromide will produce phenylsilver that contains silver or magnesium salt impurities, which destabilize it. [3] [4]

When heating phenylsilver in a speed of 5 °C/min, it decomposes at 67 °C. If the heating speed is 10 °C/min, it will explode at 47 °C. [1]

2 C6H5Ag → C6H5−C6H5 + 2 Ag [3]

References

  1. 1 2 3 Beverwijk, C. D. M.; van der Kerk, G. J. M. (1972). "The synthesis and properties of phenylsilver". Journal of Organometallic Chemistry. 43 (1): C11 –C12. doi:10.1016/S0022-328X(00)81760-X. hdl: 1874/15839 .
  2. ↑ Lenz, Tabea; Hebenbrock, Marian (2024). "Phenylsilver – an unexpected one-dimensional coordination polymer of silver(i) tetrads". Dalton Transactions. 53: 423–427. doi:10.1039/D3DT03007E.
  3. 1 2 3 J. Boersma; F.J.A. Des Tombe; F. Weijers; G.J.M. Van Der Kerk (January 1977). "A new, easy synthesis of phenylsilver". Journal of Organometallic Chemistry. 124 (2): 229–233. doi:10.1016/S0022-328X(00)90970-7 . Retrieved 2020-12-09.
  4. ↑ Reich, Rene. New organometallic compounds: Copper phenyl and silver phenyl. Compt. rend., 1923. 177: 322-324. CAN18: 2618.

Further reading

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