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
3D model (JSmol)
ChemSpider
  • 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
  • C1(=C(C(=C(C(=C1F)F)[Xe]C2=C(C(=C(C(=C2F)F)F)F)F)F)F)F
Properties
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]

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