Phenylsilver Explained

Phenylsilver is an organosilver compound with the chemical formula C6H5Ag. It is a white solid. The structure is a one-dimensional coordination polymer of silver(I) tetrads.[1]

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.[2] 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.[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.

2 C6H5Ag → C6H5-C6H5 + 2 Ag

Further reading

Notes and References

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

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