Bis(pentafluorophenyl)xenon explained

Bis(pentafluorophenyl)xenon is an unstable organic compound of xenon.[1] [2] It consists of two fluorinated phenyl rings connected to xenon.

Structure

Bis(pentafluorophenyl)xenon is a molecular substance. In the solid form it crystallises in the monoclinic system with space group P21/n.[3] The unit cell has four molecules with a = 13.635 Å. b = 8.248 Å. c = 11.511 Å, β = 102.624°. The unit cell volume is 1263.18 Å3.[4]

The molecules have carbon to xenon to carbon bonds in nearly a straight line (the bond angle is at least 175°). The carbon–xenon bond lengths are 2.35 and 2.39 Å. The two pentafluorophenyl rings are twisted by 72° with respect to each other.[3]

Properties

Bis(pentafluorophenyl)xenon decomposes above −20 °C and can explode.

Preparation

Xe(C6F5)2 is prepared from the [(CH<sub>3</sub>)<sub>4</sub>N]F catalyzed reactions of (CH3)3SiC6F5 and XeF2 in propionitrile, propionitrile/acetonitrile, acetonitrile, or CH2Cl2, at -60 to -40 °C as the first [10-Xe-2] species with two xenon-carbon bonds as a colorless solid that decomposes above −20 °C and spontaneously at 20 °C. C6F5XeF is formed  as an intermediate which has been characterized by NMR spectroscopy.

XeF2 + (CH3)3SiC6F5 → C6F5XeF + (CH3)3SiF

XeF2 + 2 (CH3)3SiC6F5 → Xe(C6F5)2 + 2 (CH3)3SiF

Xe(C6F5)2 is also formed from the reaction of C6F5XeF with Cd(C6F5)2

2 C6F5XeF + Cd(C6F5)2 → Xe(C6F5)2 + CdF2

However, the direct introduction of the C6F5 group into XeF2 with Cd(C6F5)2 is not successful.

Bis(pentafluorophenyl)xenon is crystallized from dichloromethane at −40 °C.

Reactions

Bis(pentafluorophenyl)xenon reacts with mercury to make bis(pentafluorophenyl)mercury.

Bis(pentafluorophenyl)xenon reacts with hydrogen fluoride to form pentafluorophenyl xenon fluoride C6F5XeF.In acetonitrile solution bis(pentafluorophenyl)xenon decomposes to form C6F5-C6F5 (C12F10) and xenon.[5] But in dichloromethane solution the product is mostly pentafluorobenzene.

It reacts with iodine to make (C6F5I).

Notes and References

  1. Maggiarosa . N. . Naumann . D. . Tyrra . W. . 2000 . Bis(pentafluorophenyl)xenon, Xe(C6F5)2: A Homoleptic Diorganoxenon Derivative . Angewandte Chemie International Edition . 39 . 24 . 4588–4591 . Angewandte Chemie International Edition, 39(24), 4588–4591. . 10.1002/1521-3773(20001215)39:24<4588::AID-ANIE4588>3.0.CO;2-5. 11169679 .
  2. Frohn . H.-J. . Theißen . M. . 2000 . C6F5XeF, A Key Substrate in Xenon–Carbon Chemistry: Synthesis of Symmetric and Asymmetric Pentafluorophenylxenon(II) Derivatives. . Angewandte Chemie International Edition . 39 . 24 . 4591–4593 . Angewandte Chemie International Edition, 39(24), 4591–4593. . 10.1002/1521-3773(20001215)39:24<4591::AID-ANIE4591>3.0.CO;2-8. 11169680 .
  3. Bock . Harald . Hinz-Hübner . Dirk . Ruschewitz . Uwe . Naumann . Dieter . Structure of Bis(pentafluorophenyl)xenon, Xe(C6F5)2 . Angewandte Chemie International Edition . 1 February 2002 . 41 . 3 . 448–450 . 10.1002/1521-3773(20020201)41:3<448::AID-ANIE448>3.0.CO;2-W. 12491374 .
  4. 10.5517/cc5pb7d. 2002. Bock. H.. Hinz-Hubner. D.. Ruschewitz. U.. Naumann. D.. CCDC 169453: Experimental Crystal Structure Determination. Cambridge Crystallographic Data Centre.
  5. Frohn . Hermann-Josef . Bardin . Vadim V. . November 2001 . Preparation and Reactivity of Compounds Containing a Carbon−Xenon Bond . Organometallics . 20 . 23 . 4750–4762 . 10.1021/om010490j.