Organoxenon compound

Organoxenon compounds in organic chemistry contain carbon to xenon chemical bonds. The first organoxenon compounds were divalent, such as (C₆F₅)₂Xe. The first tetravalent organoxenon compound, [C₆F₅XeF₂][BF₄], was synthesized in 2004.^[1] So far, more than one hundred organoxenon compounds have been researched.

Most of the organoxenon compounds are more unstable than xenon fluorides due to the high polarity. The molecular dipoles of xenon difluoride and xenon tetrafluoride are both 0 D. The early synthesized ones only contain perfluoro groups, but later some other groups were found, e.g. 2,4,6-trifluorophenyl.^[2]

Xe(II)

The most common bivalent organoxenon compound is C₆F₅XeF, which is always used as a precursor to other organoxenon compounds. Due to the instability of xenon fluoride, it is impossible to synthesize organoxenon compounds by using general organic reagents. Most frequently used fluorinating agents include Cd(Ar_F)₂(subscript "F" means fluorine-including aryl), C₆F₅SiF₃, and C₆F₅SiMe₃ (should be used along with fluoride).

With the use of stronger Lewis acids, such as C₆F₅BF₂, ionic compounds like [RXe][Ar_FBF₃] can be produced. Alkenyl and alkyl organoxenon compounds are prepared in this way as well, for example, C₆F₅XeCF=CF₂ and C₆F₅XeCF₃.^[2]

Some typical reactions are listed below:

{\rm {\ 2C_{6}F_{5}XeF+Cd(C_{6}F_{5})_{2}\rightarrow Xe(C_{6}F_{5})_{2}+CdF_{2}\downarrow }}

{\rm {\ C_{6}F_{5}XeF+Me_{3}SiCN\rightarrow C_{6}F_{5}XeCN+Me_{3}SiF}}

{\rm {\ C_{6}F_{5}XeF+Cd(2,4,6-C_{6}H_{2}F_{3})_{2}\rightarrow 2,4,6-C_{6}H_{2}F_{3}XeC_{6}F_{5}+CdF_{2}\downarrow }}

The third reaction also produces (C₆F₅)₂Xe, Xe(2,4,6-C₆H₂F₃)₂ and so on.

The precursor C₆F₅XeF can be prepared by the reaction of trimethyl(pentaflurophenyl)silane (C₆F₅SiMe₃) and xenon difluoride. Adding fluoride to the adduct of C₆F₅XeF and arsenic pentafluoride is another method.^[2]

Xe(IV)

In 2000, Karel Lutar and Boris Žemva et al. produced an ionic compound. They treated xenon tetrafluoride and difluoro(pentaflurophenyl)borane in dichloromethane at -55 °C:

{\rm {\ XeF_{4}+C_{6}F_{5}BF_{2}{\xrightarrow[ {-55^{o}C}]{CH_{2}Cl_{2}}}[C_{6}F_{5}XeF_{2}]^{+}BF_{4}^{-}}}

The compound is an extremely strong fluorinating agent, and it is capable of converting (C₆F₅)₃P to (C₆F₅)₃PF₂, C₆F₅I to C₆F₅IF₂, and iodine to iodine pentafluoride.^[1]

CH				He
CLi	CBe	CB	CC	CN	CO	CF	Ne
CNa	CMg	CAl	CSi	CP	CS	CCl	CAr
CK	CCa	CSc	CTi	CV	CCr	CMn	CFe	CCo	CNi	CCu	CZn	CGa	CGe	CAs	CSe	CBr	CKr
CRb	CSr	CY	CZr	CNb	CMo	CTc	CRu	CRh	CPd	CAg	CCd	CIn	CSn	CSb	CTe	CI	CXe
CCs	CBa		CHf	CTa	CW	CRe	COs	CIr	CPt	CAu	CHg	CTl	CPb	CBi	CPo	CAt	Rn
Fr	CRa	Rf	Db	CSg	Bh	Hs	Mt	Ds	Rg	Cn	Nh	Fl	Mc	Lv	Ts	Og
	↓
	CLa	CCe	CPr	CNd	CPm	CSm	CEu	CGd	CTb	CDy	CHo	CEr	CTm	CYb	CLu
	Ac	CTh	CPa	CU	CNp	CPu	CAm	CCm	CBk	CCf	CEs	Fm	Md	No	Lr

**Chemical bonds to carbon**
Core organic chemistry	Many uses in chemistry
Academic research, but no widespread use	Bond unknown

References

1 2 LeBlond, Nicolas, Lutar, Karel, Žemva, Boris (2000-01-16). "The First Organoxenon(IV) Compound: Pentafluorophenyldifluoroxenonium(IV) Tetrafluoroborate". Angewandte Chemie International Edition. 39 (2): 391–393. doi:10.1002/(SICI)1521-3773(20000117)39:2<391::AID-ANIE391>3.0.CO;2-U.
1 2 3 FROHN, H (2004-05-31). "C6F5XeF, a versatile starting material in xenon-carbon chemistry". Journal of Fluorine Chemistry. 125 (6): 981–988. doi:10.1016/j.jfluchem.2004.01.019.

Xenon compounds

Xenon(0)

AuXe₄(Sb₂F₁₁)₂

Xenon(I)

XePtF₆
XeRhF₆
XeRuF₆
XePuF₆
XeF

Xenon(II)

Organoxenon(II) compounds	XeC₆F₅F XeC₆F₅C₂F₃ XeC₆F₅CF₃ Xe(C₆F₅)₂ XeC₆F₅C₆H₂F₃ XeC₆F₅CN Xe(CF₃)₂

Xenon(IV)

XeO₂
XeF₄
XeOF₂
N(CH₃)₄XeF₅
XeCl₄

Organoxenon(IV) compounds	XeF₂C₆F₅BF₄

Xenon(VI)

XeO₃
XeF₆
XeOF₄
H₂XeO₄
(NO)₂XeF₈
CsXeF₇
RbXeF₇

Xenon(VIII)

Noble gas compounds

Helium compounds

Neon compounds

neon compounds

Argon compounds

Krypton compounds

Xenon compounds

Xe(0)	AuXe₄(Sb₂F₁₁)₂

Xe(I)	XePtF₆ XeRhF₆

Xe(II)	XeF₂ XeFPtF₅ XeFPt₂F₁₁ Xe₂F₃PtF₆ XeCl₂ Organoxenon(II) compounds

Xe(IV)	XeO₂ XeF₄ XeOF₂ N(CH₃)₄XeF₅ Organoxenon(IV) compounds

Xe(VI)	XeO₃ XeF₆ XeOF₄ H₂XeO₄ (NO)₂XeF₈

Xe(VIII)	XeO₄ H₄XeO₆

Radon compounds

Rn(II)	RnF₂ RnFSb₂F₁₁

Rn(VI)	RnO₃

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CH																	He
CLi	CBe											CB	CC	CN	CO	CF	Ne
CNa	CMg											CAl	CSi	CP	CS	CCl	CAr
CK	CCa	CSc	CTi	CV	CCr	CMn	CFe	CCo	CNi	CCu	CZn	CGa	CGe	CAs	CSe	CBr	CKr
CRb	CSr	CY	CZr	CNb	CMo	CTc	CRu	CRh	CPd	CAg	CCd	CIn	CSn	CSb	CTe	CI	CXe
CCs	CBa		CHf	CTa	CW	CRe	COs	CIr	CPt	CAu	CHg	CTl	CPb	CBi	CPo	CAt	Rn
Fr	CRa		Rf	Db	CSg	Bh	Hs	Mt	Ds	Rg	Cn	Nh	Fl	Mc	Lv	Ts	Og
		↓
		CLa	CCe	CPr	CNd	CPm	CSm	CEu	CGd	CTb	CDy	CHo	CEr	CTm	CYb	CLu
		Ac	CTh	CPa	CU	CNp	CPu	CAm	CCm	CBk	CCf	CEs	Fm	Md	No	Lr

CH																	He
CLi	CBe											CB	CC	CN	CO	CF	Ne
CNa	CMg											CAl	CSi	CP	CS	CCl	CAr
CK	CCa	CSc	CTi	CV	CCr	CMn	CFe	CCo	CNi	CCu	CZn	CGa	CGe	CAs	CSe	CBr	CKr
CRb	CSr	CY	CZr	CNb	CMo	CTc	CRu	CRh	CPd	CAg	CCd	CIn	CSn	CSb	CTe	CI	CXe
CCs	CBa		CHf	CTa	CW	CRe	COs	CIr	CPt	CAu	CHg	CTl	CPb	CBi	CPo	CAt	Rn
Fr	CRa		Rf	Db	CSg	Bh	Hs	Mt	Ds	Rg	Cn	Nh	Fl	Mc	Lv	Ts	Og
		↓
		CLa	CCe	CPr	CNd	CPm	CSm	CEu	CGd	CTb	CDy	CHo	CEr	CTm	CYb	CLu
		Ac	CTh	CPa	CU	CNp	CPu	CAm	CCm	CBk	CCf	CEs	Fm	Md	No	Lr

Organoxenon compound

Xe(II)

Xe(IV)

See also

References

CH																	He
CLi	CBe											CB	CC	CN	CO	CF	Ne
CNa	CMg											CAl	CSi	CP	CS	CCl	CAr
CK	CCa	CSc	CTi	CV	CCr	CMn	CFe	CCo	CNi	CCu	CZn	CGa	CGe	CAs	CSe	CBr	CKr
CRb	CSr	CY	CZr	CNb	CMo	CTc	CRu	CRh	CPd	CAg	CCd	CIn	CSn	CSb	CTe	CI	CXe
CCs	CBa		CHf	CTa	CW	CRe	COs	CIr	CPt	CAu	CHg	CTl	CPb	CBi	CPo	CAt	Rn
Fr	CRa		Rf	Db	CSg	Bh	Hs	Mt	Ds	Rg	Cn	Nh	Fl	Mc	Lv	Ts	Og
		↓
		CLa	CCe	CPr	CNd	CPm	CSm	CEu	CGd	CTb	CDy	CHo	CEr	CTm	CYb	CLu
		Ac	CTh	CPa	CU	CNp	CPu	CAm	CCm	CBk	CCf	CEs	Fm	Md	No	Lr