Bis(pentafluorophenyl)xenon

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

Bis(pentafluorophenyl)xenon

Names
IUPAC name bis(2,3,4,5,6-pentafluorophenyl)xenon
Identifiers
CAS Number	328379-54-0
3D model (JSmol)	Interactive image
ChemSpider	21781720
PubChem CID	57397093
CompTox Dashboard (EPA)	DTXSID00725423
InChI InChI=1S/C12F10Xe/c13-1-3(15)7(19)11(8(20)4(1)16)23-12-9(21)5(17)2(14)6(18)10(12)22 Key: YAQWCIUPEXZIQW-UHFFFAOYSA-N
SMILES C1(=C(C(=C(C(=C1F)F)[Xe]C2=C(C(=C(C(=C2F)F)F)F)F)F)F)F
Properties
Chemical formula	C12F10Xe
Molar mass	465.409 g·mol−1
Density	2.447 g/cm3 (at 50 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[1]

Preparation

Xe(C₆F₅)₂ is prepared from the [(CH₃)₄N]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.^[1] C₆F₅XeF^[1][2] 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]

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.^[2]

Bis(pentafluorophenyl)xenon is crystallized from dichloromethane at −40 °C.^[3]

Reactions

Bis(pentafluorophenyl)xenon reacts with mercury to make bis(pentafluorophenyl)mercury.^[1]

Bis(pentafluorophenyl)xenon reacts with hydrogen fluoride to form pentafluorophenyl xenon fluoride C₆F₅XeF.^[2] In acetonitrile solution bis(pentafluorophenyl)xenon decomposes to form C₆F₅-C₆F₅ (C₁₂F₁₀) and xenon.^[5] But in dichloromethane solution the product is mostly pentafluorobenzene.^[5]

It reacts with iodine to make pentafluoroiodobenzene (C₆F₅I).^[2]