Bis(pentafluorophenyl)xenon
{{Chembox
| IUPACName = bis(2,3,4,5,6-pentafluorophenyl)xenon
| ImageFile = Bis(pentafluorophenyl)xenon conformation.png
|Section1 = {{Chembox Identifiers
| PubChem = 57397093
| CASNo = 328379-54-0
| DTXSID = DTXSID00725423
| ChemSpiderID = 21781720
| StdInChI=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
| StdInChIKey = 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
}}
|Section2 = {{Chembox Properties
|C=12|F=10|Xe=1
| Density = 2.447 g/cm3 (at 50 K)
}}
}}
Bis(pentafluorophenyl)xenon is an unstable organic compound of xenon.{{Cite journal |last1=Maggiarosa |first1=N. |last2=Naumann |first2=D. |last3=Tyrra |first3=W. |year=2000 |title=Bis(pentafluorophenyl)xenon, Xe(C6F5)2: A Homoleptic Diorganoxenon Derivative |journal=Angewandte Chemie International Edition |volume=39 |issue=24 |pages=4588–4591 |url=https://doi.org/10.1002/1521-3773(20001215)39:24 |archive-url= |access-date= |publisher=Angewandte Chemie International Edition, 39(24), 4588–4591. |doi=10.1002/1521-3773(20001215)39:24<4588::AID-ANIE4588>3.0.CO;2-5|pmid=11169679 }}{{Cite journal |last1=Frohn |first1=H.-J. |last2=Theißen |first2=M. |year=2000 |title=C6F5XeF, A Key Substrate in Xenon–Carbon Chemistry: Synthesis of Symmetric and Asymmetric Pentafluorophenylxenon(II) Derivatives. |journal=Angewandte Chemie International Edition |volume=39 |issue=24 |pages=4591–4593 |url=https://doi.org/10.1002/1521-3773(20001215)39:24<4591::AID-ANIE4591>3.0.CO;2-8 |publisher=Angewandte Chemie International Edition, 39(24), 4591–4593. |doi=10.1002/1521-3773(20001215)39:24<4591::AID-ANIE4591>3.0.CO;2-8|pmid=11169680 }} 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.{{cite journal |last1=Bock |first1=Harald |last2=Hinz-Hübner |first2=Dirk |last3=Ruschewitz |first3=Uwe |last4=Naumann |first4=Dieter |title=Structure of Bis(pentafluorophenyl)xenon, Xe(C6F5)2 |journal=Angewandte Chemie International Edition |date=1 February 2002 |volume=41 |issue=3 |pages=448–450 |doi=10.1002/1521-3773(20020201)41:3<448::AID-ANIE448>3.0.CO;2-W|pmid=12491374 }} 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.{{cite journal |doi=10.5517/cc5pb7d|year=2002|last1=Bock|first1=H.|last2=Hinz-Hubner|first2=D.|last3=Ruschewitz|first3=U.|last4=Naumann|first4=D.|title=CCDC 169453: Experimental Crystal Structure Determination|publisher=Cambridge Crystallographic Data Centre}}
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.
Properties
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. 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.{{cite journal |last1=Frohn |first1=Hermann-Josef |last2=Bardin |first2=Vadim V. |date=November 2001 |title=Preparation and Reactivity of Compounds Containing a Carbon−Xenon Bond |journal=Organometallics |volume=20 |issue=23 |pages=4750–4762 |doi=10.1021/om010490j}} But in dichloromethane solution the product is mostly pentafluorobenzene.
It reacts with iodine to make {{chem name|pentafluoroiodobenzene}} (C6F5I).
References
{{Reflist}}{{Xenon compounds}}{{Noble gas compounds}}{{Fluorine compounds}}