8??halogens and noble gases

8 Halogens and noble gases

A. K. Brisdon*

Department of Chemistry, UMIST, Manchester, UK M60 1QD

Forty years after the isolation of the first noble-gas compound there has been some-what of a renaissance in this area with, this year, four new Au–Xe compounds beingreported and, using matrix techniques, HKrF and xenon-uranium compounds beingformed and stabilised.

1 Introduction

This chapter reviews the year 2002 literature for the elemental halogens and the noblegases and compounds containing these elements in their positive oxidation states. Asin previous years, publications which involve halide, interhalide or oxohalide anions ascounter ions are generally not described.

2 Halogens

The importance of halogen chemistry in atmospheric chemistry is well known — notleast for the part played by these elements, and their compounds, in ozone depletion.There has been considerable recent interest in the processes occurring at the marineboundary layer involving halogens. In particular it has been determined that halogenspecies significantly affect ozone concentrations immediately after sunrise.1 Modellingof this phenomenon suggests that acid-catalysed activation of bromine from sea saltaerosol occurs and is responsible for a distinct diurnal variation in atmospheric con-centrations of bromine-containing compounds.2 In a related study it was shown thathalogen-containing species were more effective at oxidising sulfur() species in seasalt aerosols than either hydrogen peroxide or ozone.3 A previously unrecognizedsource of aerial particles based on iodine chemistry has also been proposed.4 Experi-ments suggest that these particles can be formed from condensable iodine-containingvapours derived from organic iodine-containing sources such as CH2I2. Such a find-ing, which may be expected to have a significant effect on global radiative forcing, isconsistent with the previously noted differences between chlorine and bromine con-centrations which are lowered in sea-salt aerosols and iodine concentrations thatincrease. Of relevance to this area is a report of biological methylation of a wide rangeof elements, including the halogens (by marine kelp and seaweeds).5

DOI: 10.1039/b211479h Annu. Rep. Prog. Chem., Sect. A, 2003, 99, 115–123 115

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. View Article Online / Journal Homepage / Table of Contents for this issue

http://dx.doi.org/10.1039/b211479h

http://pubs.rsc.org/en/journals/journal/IC

http://pubs.rsc.org/en/journals/journal/IC?issueid=IC003099

Research into the adducts formed between halogens and Lewis bases, in the past awidespread research activity, appears to be waning, with many fewer studies, eitherpractical or theoretical, of these systems being reported. The interaction of water withdibromine in the gas phase has been studied by rotational spectroscopy, thus complet-ing the series of H2O�X2 and H2O�XY adducts (X, Y = halogens) studied in this way.6

All these adducts have now been determined to be pyramidal at oxygen with anglesbetween the H2O and dihalogen internuclear axes lying between 41 and 56�. A com-parison across the series shows that the interactions between the halogen moiety andwater increases in the order F2<Cl2<Br2<BrCl<ClF<ICl.

The interaction of diiodine with some heterocyclic thioamides has been investi-gated. With thiazolidine-2-thione a rare example of an S–I�–S dimer is produced,the solid-state structure of which is shown in Figure 1. The unit cell contains threemoieties, the dimer, an I3

� counter-ion and diiodine.7 The S–I–S unit is linear withd(S–I) = 2.654(6) Å and the S(2)–C(2) distance at 1.65(3) Å being one of the shortestsuch distances known.

Neutral dihalogen molecules have also been found to provide effective linkers inmetal complexes. When powdered chromium is heated with 1,2-dicyanobenzene anddiiodine diiodo[phthalocyaninato]chromium() complexes result, which in the solidstate are linked by neutral (as determined from X-ray bond length data) diiodinemolecules to form a one-dimensional polymer.8 The reaction of [NBu4][PtX3(CO)](X = Cl, Br) with dibromine gives rise to the new platinum() salts [NBu4]2[Pt2-Br10].(Br2)7 and [NBu4]2[PtBr4Cl2].(Br2)6 which in the solid state form a polymericnetwork of bromine–bromine interactions.9

Fig. 1 ORTEP representation of the diiodine adduct of {(thiazolidine-2-thione)2I�}�I3

��I2,thermal ellipsoids are shown at the 50% probability level.

116 Annu. Rep. Prog. Chem., Sect. A, 2003, 99, 115–123

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. View Article Online


The introduction of halogens into molecules can be achieved in a variety of differ-ent ways. A new protocol for introducing iodine into sterically hindered benzenemolecules has been reported using elemental iodine activated by 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor, F-TEDA-BF4).10 Activation of fluorine is not required, quite the reverse, its extreme reactivityneeding to be controlled; further reports on the use of fluorine diluted in nitrogendemonstrate that it is possible to controllably fluorinate a range of hydrocarbons in anelectrophilic fashion using elemental fluorine.11 Alternative routes rely on more readilyhandled fluorinating agents; the dialkylether/poly(hydrogen fluoride) complexes havebeen proposed as new, convenient and effective fluorinating agents.12 Thus, the com-plex of dimethylether/poly(hydrogen fluoride) which is calculated to have a cyclicpoly(hydrogen fluoride) bridged structure introduces fluorine into alcohols andalkenes effectively at room temperature. Finally, calculations suggest that endohedralencapsulation of Cl2, Br2, I2, BrCl, ICl and IBr within C70 should give rise to stablecompounds.13

3 Interhalogens and polyhalide ions

Interhalogen compounds are often used as tests for structure and bonding theories. Astudy of the chemical bonding in hypervalent molecules using the atoms-in-molecules(AIM) approach, including ClF3, BrF3, ClF5 and BrF5, concludes that the bonding inhypervalent molecules need be treated no differently from that in non-hypervalentmolecules.14 A review of the bonding in polyiodides in terms of interactions betweenI�, I2 and I3

� units, and computational modelling of these interactions has alsoappeared.15

The use of interhalogens as halogenating agents is well known; they may also beused as promoters of reactions. Studies of interhalogen/silver triflate promoted glyco-sylation reactions have shown that whilst variable yields of ca. 40% can be obtainedusing ICl, in this application they can be substantially increased (to 74%) using IBr. Inthis system there is no apparent activation of the interhalogen, instead the silver ionsare believed to reduce the halide nucleophile concentration.16

A review of the structures of the BrF4� and IF4

� cations has been undertakenfollowing the recognition that the observed and predicted structures for the iso-electronic series ClF4

�, BrF4�, IF4

�, SF4, SeF4 and TeF4 are in agreement for theneutral species, but not for the cations. The latest data resolves these problems follow-ing a redetermination of the solid-state structures of BrF4

� and IF4�.17 In both cases

these cations adopt a trigonal bipyramidal shape with one equatorial site occupied bya lone pair of electrons. However strong anion–cation interactions in [BrF4]

�[Sb2F11]�

result in an infinite zigzag chain and distortion of the equatorial F–Br–F bond angle.In comparison, for [IF4]

�[SbF6]� an infinite polymeric sheet motif is observed due to

four short I � � � F interactions which results in a compression of the axial F–I–Fangle.

Annu. Rep. Prog. Chem., Sect. A, 2003, 99, 115–123 117

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4 Halogen oxides and organoiodine compounds

The environmental chlorine reservoir species chlorine nitrate, ClONO2, is well known,but analogues for the heavier elements are not. A study of the recombination of IOwith NO2, to give iodine nitrate, reports that at temperatures below 290 K photolyticdissociation dominates and that this has potential implications for ozone destructionin the lower troposphere.18 The kinetics of another environmentally relevant species,ClO2, has been studied in detail, this time in aqueous solution.19 The rate of electrontransfer between ClO2 and BrO2 is enhanced by the presence of a nucleophile, the rateof this process being enhanced not by the nucleophilicity but the degree of interactionbetween the nucleophile and ClO2.

The trigonal bipyramidally-based shapes of the halogen oxide-fluorides of the typeXOF3 have been determined from spectroscopic methods, as previously has beenconfirmed for IOF3 using X-ray diffraction methods. Now the solid-state structures ofClOF3 and BrOF3 have been reported as well. Both show the anticipated trigonalbipyramidal geometry around the central halogen atom with two axial fluorideligands. Interestingly, the structure of ClOF3, shown in Figure 2, which is described asa tube-like stacking of pseudo-hexagonal, eight-membered rings in which the different‘tubes’ are weakly interconnected, gives rise to a formal coordination number of 7 toeach chlorine atom. This is higher than the usual maximum coordination number ofsix, such as is found in the ClF6

� anion.20

Fig. 2 ORTEP representation of the solid state structure of IOF3, showing the interactionsbetween adjacent molecules, thermal ellipsoids are drawn at the 50% probability level.(Reproduced by permission from Z. Anorg. Allg. Chem., 2002, 628, 1991, Copyright 2002,John Wiley & Sons.)


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High-oxidation state and hypervalent iodine reagents continue to attract consider-able attention as mild and selective oxidising agents in organic synthesis due to theirlow toxicity and ready availability, and this area has been reviewed.21,22 Some of thebest known reagents of this type are derivatives of o-iodoxybenzoic acid (IBX, 1), aniodine() reagent used for selective oxidation reactions. Modifications of IBX havebeen reported which resulted in a compound (mIBX, 2) that may be used in water andother environmentally benign solvent systems.23 The use of water as a solvent systemfor the facile and clean oxidation of alcohols using an iodine() reagent, PhIO in thepresence of KBr has also been reported.24

The use of iodine() oxide, I2O5, and its acid, HIO3, have been demonstrated for themild and atom-efficient dehydrogenation of a wide range of substrates.25 When eitherof these compounds are added to DMSO 1 : 1 complexes (3 and 4) are formed whichare mild and efficient oxidants and can be used for dehydrogenation of aldehydes andketones.

With so many applications of moderate and high oxidation-state iodine compoundsit is not surprising that new analogues are sought. This year sees the first iodine()compound with a chelating polydentate nitrogen ligand, [PhI(O)(2,2�-bipy)](OTf )2,being reported,26 and a new direct synthesis of alkenyl(phenyl)iodonium salts fromalkynes and PhIO.27

5 Noble gases and noble gas compounds

The year under review marks forty years since the first report of a chemical reactionof a Group-18 element by Neil Bartlett so necessitating a change in the name of theseelements from the inert gases to the noble gases; fittingly a considerable number ofnoble gas publications appeared this year.

Originally the noble gasses were used precisely because they were believed to beinert, and in many contexts they are, for example they are often the gases of choice toform low-temperature inert matrices for spectroscopic studies and this area hasrecently been reviewed.28 However, it is now obvious that noble gas matrices are notalways inert, and this approach has been used to generate new noble gas species.HKrF, the analogue of HArF, reported last year, has been prepared by the photolysisof HF in a krypton matrix followed by annealing of the matrix.29 Subsequent studiesidentified a number of different matrix-site geometries for compounds of the typeHRgY (Rg = Rare Gas atom).30 These calculations may help to explain the effects thatwarming the matrix has on HRgF molecules. Since many of these species are assigned

Scheme 1


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with the aid of computational calculations a study has been undertaken whichconsiders the accuracy of calculations, at a variety of different levels of theory,towards these types of materials.31 The principal conclusion is that DFT calculationsalone are not, generally, sufficient for computational work in this area. Using what isnow a well tested approach the photolysis of H2S, HI and H2CO in solid xenonmatrices are reported to generate the species HXeSH, HXeI and HXeH according toelectronic absorption spectroscopic studies.32 More intriguing is the report that whenuranium atoms, derived from the laser ablation of an uranium target, are cocondensedwith carbon monoxide and argon and xenon species of the type CUO (Ar)4�n(Xe)n

(n = 1–4) are produced.33,34 The data from these studies show that four noble gas atomsare intimately involved in the coordination sphere of uranium, making this the firstcharacterisation of a neutral complex involving four noble-gas atoms around onemetal centre.

Theoretical studies identify a number of potential targets for future studies, includ-ing the suggestions that xenon should insert into the C–H bonds of a variety ofhydrocarbons including acetylene, benzene and phenol.35 Further, the authors suggestthat it may be possible to insert two xenon atoms into molecules, such as acetylene, togenerate molecules of the type H–Xe–C2–Xe–H.

The report last year of the preparation of the gold–xenon complex [Au-Xe4]

2�[Sb2F11]�

2 has resulted in the search for further related species by varying theconditions of reaction and concentrations of the reagents. In this way the new Au()species cis-[AuXe2]

2�[Sb2F11]�

2 was prepared from a 2 : 1 HF : SbF5 solution of AuF3

in the presence of a pressure of xenon.36 The structure of this complex, which isshown in Figure 3, shows a square-planar cis-arrangement of two xenon and twobridging fluoride ligands around the gold centre. The average Au–Xe distanceis slightly shorter, 2.665 Å, than in the previously known [AuXe4]

2� species[d(Au–Xe)av = 2.752 Å] and the complex is slightly more thermally stable. The trans-[AuXe2]

2�[SbF6]�

2 complex has also been prepared, but in this case from finely dividedgold powder dissolved in an HF–SbF5 solution pressurised with xenon and oxidisedwith XeF2. The Au � � � F distances in the trans-complex are markedly shorter than inthe cis-analogue, presumably due to the different basicity of SbF6

� and Sb2F11�. At

lower xenon pressures a binuclear Au–Xe complex of remarkable stability, decompos-ing only slightly below room temperature, containing a Z-shaped [Xe–Au–F–Au–Xe]3� ion is prepared. Finally, in a less acidic solution (HF : SbF5 = 5 : 1) a gold()xenon complex, trans-[AuXe2F]2�[SbF6]

�[Sb2F11]�, may be synthesised. Once again

the single crystal structure has been obtained and shows that the gold centre resides ina square-planar environment with the gold surrounded by two trans xenon atoms withthe terminal fluoride opposite a bridging fluoride ligand from the SbF6

� anion.The nature of the Au–Rg bond in the [AuRg4]

2� complexes has been studied com-putationally, which concluded that the gold–rare gas bonding is dominated by electro-static interactions and that the unpaired electron density (0.16 e for [AuXe4]

2�) isconcentrated on the gold atom.37

The solid-state structure of the first homoleptic organoxenon() compound,Xe(C6F5)2, the synthesis of which was reported last year, has been reported based onX-ray powder data obtained at low temperature (the compound explodes at �20 �C).38

The C–Xe–C unit is almost linear [178(3)�] and the Xe–C bonds are 0.3 Å longer thanthe corresponding bond in [Xe(C6F5)][AsF6]. The two C6F5 rings are twisted by 72.5�


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with respect to each other, this torsion angle being comparable with that observed inthe isoelectronic [I(C6F5)2]

� ion.The coordination chemistry of xenon difluoride has received much attention this

year. The starting point for many of these studies are metal() hexafluoroarsenates()which represent excellent starting materials for the preparation of new coordinationcompounds due to the practically naked metal centres and weakly interacting AsF6

�

anions. Thus when Ln(AsF6)3 [Ln = lanthanide element] is reacted with XeF2 inanhydrous HF, coordination complexes of the type [Ln(XeF2)3](AsF6)3 result.39 In asimilar way [M(XeF2)3](AsF6)2 [M = Pb, Sr] 40 and Ba(SbF6)2�5XeF2

41 may be pre-pared. The latter compound representing the first example of a xenon() compoundof barium.

XeF2 is a very mild and convenient fluorinating or oxidising agent, examples ofsuch applications this year include a study of the fluorination of C60Br24 with XeF2

42

and the formation of Ni2F5, probably an important intermediate in the electro-chemical fluorination (ecf ) process, from RNiF3.

43 The oxidative fluorination oftris(anthryl)bismuth 44 and its phosphorus analogues 45 gave the difluorides whilstthe reaction of R2Te with XeF2 followed by reaction with Me3SiN3 results in the

Fig. 3 ORTEP representation of the solid state structure of cis-[AuXe2]2�[Sb2F11]

�2, showing

the interactions between adjacent molecules, thermal ellipsoids are drawn at the 50% probabilitylevel. (Reproduced by permission from Angew. Chem., Int. Ed., 2002, 41, 454, Copyright 2002,John Wiley & Sons.)


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formation of novel organotellurium() azides.46 Meanwhile, reaction of RfBF2 andK[RfBF3] with xenon difluoride in HF resulted in either xenodeborylation, formationof C6F5Xe�, or fluorine addition to the Rf group.47 Fluoroalkyl-substituted com-pounds were found to be relatively inert and when Rf = alkenyl exclusive fluorineaddition occurred, for fluoroaryl compounds a preference for xenodeborylationoccurred, as shown in Scheme 2.

The report last year of fluorine-18 exchange with XeF2 in the absence of a carrierdoes not appear to be correct. Attempts to repeat the work were unsuccessful and haveresulted in a re-investigation of the fluorine exchange processes of XeF2 which sug-gested that the exchange between XeF2 and F� proceeds via the formation of XeF3

�.48

Krypton forms a more limited range of compounds than xenon and these have beencomprehensively reviewed.49 However, endohedrally encapsulated Kr@C60 has beenreported following the pressurisation of C60 under krypton, followed by chromato-graphic separation.50 A similar compound is possible with xenon, and when 129Xeenriched xenon gas is used the 129Xe NMR spectrum may be obtained.51 This NMRstudy suggests that a much larger interaction exists between the xenon nucleus and theπ-system of C60 than is observed with helium in He@C60. Continuous flow hyperpolar-ised 129Xe NMR studies have been applied for the first time to microporous films andappears to offer methods for recording information about the porosity of very smallamounts of materials.52 Xenon-129 is usually the NMR-active xenon nucleus of choicefor study due to the quadrupolar nature of the alternative, 131Xe, nucleus. However, thefirst 131Xe-NMR study of a chemically bound species has now been reported, in this caseof the highly-symmetric, and thermally unstable, XeO4 molecule.53

Abbreviations

Rf perfluoroalkyl or perfluoroaryl residueTfO triflate

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6/1–16.

Scheme 2


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8??halogens and noble gases

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