Oxalate fluoride

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An oxalate fluoride is a mixed anion compound contains both oxalate and fluoride anions. Many of these compounds have high birefringence. [1]

Contents

With nonmetals, some are related to the oxalatophosphates and oxalatoborates with the addition of fluoride.

Formation

For some metal oxalate complexes, fluoride can displace some oxalate. This happens with aluminium. [2]

With gallium the reverse happens, and oxalate displaces fluoride ligands. [2]

Use

Difluorooxalaotoborates are under investigation as electrolytes, or electrolyte additives in lithium ion batteries or supercapacitors. Their advantage is greater thermal stability, up to 200 or 300 °C, ability to form ionic liquids, and for supercapacitors, support for higher voltages (3 volts). [3]

List

formulanamecrystalspace groupcellvolumedensitycommentref
N(CH3)4BF2C2O4tetramethylammonium difluoro(oxalato)borate [4]
N(CH2CH3)4BF2C2O4tetraethylammonium difluoro(oxalato)borate [5]
triethylmethylammonium difluoro(oxalato)boratemelt 15 °C; white [6]
N(-CH2CH2CH2CH2-)(CH2CH2CH3)(CH3)BF2C2O4N-Propyl-N-Methylpyrrolidinium Difluoro(oxalato)borate (Py13DFOB)melt 3.21 °C [7]
N(-CH2CH2CH2CH2-)(CH2CH2CH2CH3)(CH3)BF2C2O4N-butyl-N-methylpyrrolidinium difluoro(oxalato)borate (Py14DFOB)melt −5 °C [8]
N(-CH2CH2CH2CH2-)(CH2CH2CH2CH2CH3)(CH3)BF2C2O4N-pentyl-N-methylpyrrolidinium difluoro(oxalato)borate (Py15DFOB)glass transition −74 °C [8]
N(-CH2CH2CH2CH2-)(CH2CH2CH2CH2CH2CH3)(CH3)BF2C2O4N-hexyl-N-methylpyrrolidinium difluoro(oxalato)borate (Py16DFOB)melt 31 °C [8]
1-ethyl-1-methylpyrrolidinium difluoro(oxalato)boratemelt 10 °C; white [6]
N-ethoxyethyl-N-methylpiperidinium difluoro(oxalato)borate [3]
1-ethyl-3-methylimidazolium difluoro(oxalato)borate, [C2mim][DFOB] [6]
1-butyl-3-methylimidazolium difluoro(oxalato)borate [6]
N-ethoxyethyl-N-methylpiperidinium difluoro(oxalate)borateionic liquid, gl;ass transition -70 °C [9]
N-propyl-N-methylpiperidinium difluoro(oxalate)borateionic liquid [9]
LiBF2C2O4lithium difluoro(oxalato)borateorthorhombicCmcma = 6.2623 b = 11.437 c = 6.3002 Z = 4451.22 [10]
LiBF2C2O4·2H2Olithium difluoro(oxalato)borate dihydratemonoclinicP21/ca = 9.5580 b = 12.7162 c = 5.4387 Z = 4634.63 [10]
NaBF2C2O4sodium difluoro(oxalato)boratetetragonalI41mda=7.7316 c=8.5343510.16 [11]
Na(C2BF2O4)(CH3CN)2orthorhombicPnmaa=11.6932 b = 14.1254 c = 6.5130 Z=41075.76B tertrahedral coordination by 2 F and twice by -OCCO- [12]
Na2Mn2(C2O4)2.5F·2H2OtriclinicP1a =7.9129 b=8.8497 c=8.9252 α=74.623° β=72.361° γ=78.193°birefringence 0.064@550 nm [13]
Na3Al(C2O4)2F2.3H2Osoluble [2]
triethylmethylphosphonium difluoro(oxalato)boratemelt 9 °C; white [6]
diethylisobutylmethylphosphonium difluoro(oxalato)boratemelt 23 °C; white [6]
triisobutylmethylphosphonium difluoro(oxalato)borate [6]
tributylethylphosphonium difluoro(oxalato)borate [6]
lithium tetrafluoro(oxalato)phosphate (LiTFOP)Octahedral arrangement; P-OCCO- ring [14]
lithium difluorobis bis (oxalato) phosphate (LiDFBOP)Octahedral arrangement Two F trans on P; two oxalate diligands on equator [14]
K3Al(C2O4)2F2.3H2Osoluble [2]
[NH4]2VO2F(C2O4) [15]
[N(CH3)4]2VO2F(C2O4) [15]
Na2VO2F(C2O4) [15]
K2VO2F(C2O4) [15]
[NH4][Cr(H2O)2F2(C2O4)]green [16]
[NH4]3[Cr(C2O4)2F2]·5H2Ogreen [17]
[NH4]3[Cr(C2O4)F4]·4H2O [17]
PyH[Cr(H2O)2F2(C2O4)] Py=pyridinegreen [16]
enH2[Cr(H2O)2F2(C2O4)]2. 2H2O en=ethylenediaminegreen [16]
[Cr(en)(H2O)2(C2O4)]2F. 2H2O en=ethylenediamine [16]
[Cr(en)2(C2O4)]2F. 2H2O en=ethylenediamine [16]
Na[Cr(H2O)2F2(C2O4)]. H2Ogreen [16]
Na3[Cr(C2O4)2F2]·5H2Ogreen [17]
Na3[Cr(C2O4)F4]·9H2O [17]
K[Cr(H2O)2F2(C2O4)]green; 2 water and two fluorides in cis position [16]
K3[Cr(C2O4)2F2]·5H2Ogreen [17]
K3[Cr(C2O4)F4]·3H2O [17]
[NH4][MnF(C2O4)]pale pink [18]
[NH4]2Mn(C2O4)F3pink; CAS 94138-08-6 [19]
pyH[MnF2(C2O4)(H2O)2]monoclinicI2/aa = 7.2260 b = 15.2398 c = 9.916 β = 98.22° Z = 4Octahedral coordination on Mn, Cis-F opposite oxalate. 2 aqua is trans [20]
Na[MnF(C2O4)]·2H2Opale pink [18]
Na2Mn(C2O4)F3pink; CAS 94138-06-4 [19]
Na2Mn2(C2O4)2.5F·2H2OtriclinicP1a = 7.9129 b = 8.8497 c = 8.9252 α = 74.623oβ = 72.361 oγ = 78.193 o, Z = 2birefringence 0.064@550 nm; light yellow [1]
K[MnF(C2O4)]pale pink [18]
K2Mn(C2O4)F3pink; CAS 4138-07-5; [19]
Na2Fe(C2O4)F2monoclinicC12/c1a=15.8349 b=5.962 c=12.2784

β=111.968° Z=8

1075.02.816green [21]
[NH4]3[Fe(C2O4)2F2]·H2O [22]
[NH4][Fe(C2O4)F2]·3H2O [22]
Na[Fe(C2O4)F2]·2H2O [22]
Fe(phen)3(BF4)(C2O4BF2)∙H2O

phen = 1,10-phenanthroline

tris(1,10-phenanthroline)-iron tetrafluoroborate [ethanedioato](difluoro)borate monohydrateorthorhombicPca21a=10.816 b=16.929 c=19.491 [23]
(imidH)2[Fe2(C2O4)F6]orthorhombicPbana=9.143 b=20.837 c=3.890 Z=2ladder, oxalate rungs [24]
[Fe2(C2O4)F4(DMSO)4]monoclinicP21/na=7.259 b=11.409 c=13.374 β=97.26° Z=2dimer, oxalate bridged [24]
Na3[Fe(C2O4)2F2]·4H2Olight green [22]
KFe(C2O4)ForthorhombicCmc21a=7.7633 b=11.8767 c=10.4206red or orange [25]
K[Fe(C2O4)F2]·2H2Oyellowish green [22]
K2[Fe(C2O4)2F]·3H2O [22]
K3[Fe(C2O4)2F2]·2.8H2Olight green [22]
Co(NH3)6Al(C2O4)2F2.3H2Oorange yellow; insoluble [2]
[Co(NH3)6][Cr(C2O4)2F2]·6H2Opale green [17]
[Co(NH3)6][Cr(C2O4)F4]·4H2Opale green [17]
[Co(NH3)6][Cr(H2O)2F2(C2O4)]3. 2H2Oyellowish-green; sparingly soluble [16]
[Co(en)3][Cr(C2O4)2F2]·7H2Opale green [17]
[Co(en)3][Cr(C2O4)F4]·3H2Opale green [17]
[Co(en)3][Cr(H2O)2F2(C2O4)]3. 3H2Oyellowish green [16]
[Co(NH3)6][Fe(C2O4)F2]3·6H2Oorange yellow [22]
[Co(en)3][Fe(C2O4)F2]3orange yellow [22]
[Co(NH3)6]2[Fe(C2O4)2F]3·9H2Oorange yellow [22]
[Co(en)3]2[Fe(C2O4)2F]3·4H2Oorange yellow [22]
[Co(NH3)6][Ga(C2O4)2F2].3H2Oinsoluble [2]
Ni[Cr(H2O)2F2(C2O4)]2. 2H2Ogreen [16]
Na2[GeF2(C2O4)2]·5.5H2O [26]
K2[GeF2(C2O4)2]·1.5H2O [26]
K2Ge(C2O4)2F2·2H2O [27]
Rb2VO2F(C2O4) [15]
Rb2Ge(C2O4)2F2·2H2O [27]
Rb2GeC2O4F4 [27]
[YF(C2O4)(H2O)2]·2H2O [28]
K4Zr(C2O4)3F2·3H2O [29]
Zr4O3F2(C2O4)4 · 2H2O [30]
K14Zr4 (C2O4)5F20·2H2O [29]
Na2ZrC2O4F4·2H2O [29]
Na2Zr2C2O4F8·4H2O [29]
K2ZrC2O4F4·2H2O [29]
KZr2(OH)3F2(C2O4)2 · 4H2O [30]
KZrF3C2O4 [31]
KZrF3C2O4 · 3H2O [30]
K2ZrF4C2O4 [31]
K2ZrF4C2O4 · 2H2O [30]
K3Zr(C2O4)2F3· 3H2O [29]
K3ZrF5C2O4 [30]
K4ZrF2(C2O4)3 ⋅ 2H2O [30]
K4Zr(C2O4)2CO3F2·5H2O [32]
Rb2ZrC2O4F4·2H2O [29]
Rb2Zr2C2O4F8·4H2O [29]
Rb3Zr(C2O4)2F3· 3H2O [29]
Na3[NbO(C2O4)2F2]·3H2O [33]
K3[NbO(C2O4)2F2]·3H2O [33]
K3[Nb(C2O4)3F2]·5H2O [33]
Rb3[NbO(C2O4)2F2]·3H2O [33]
Rb4[Mo2O4 (C2O4)2F2]orthorhombica=1065 b=8.88 c=8.09 Z=23.52 [34]
In(C2O4)F. 3H2O [35]
NH4[In(C2O4)F2].2H2O [35]
Na[In(C2O4)F2].2H2O [35]
K[In(C2O4)F2].3H2O [35]
K2[InF3(C2O4)H2O]monoclinicP21/ca=7.6943 b=9.8135

c=7.7252 β=109.648 Z=4

549.353.300 [36]
Rb2[InF3(C2O4)H2O]monoclinicP21/ca=7.8308 b=9.9671

c=7.9327 β=111.266 Z=4

576.983.676 [36]
[Co(NH3)6][In(C2O4)2F2].2H2O [35]
[Sn(C2O4)F-][NH4+]monoclinicP21/ca = 8.2736 b = 9.6386 c = 7.7473 β = 111.229° Z = 4 [37]
NaSnC2O4F·H2OtriclinicP1a = 5.9880 b = 7.2468 c = 8.2925 α = 111.020°β = 107.986° γ = 96.873° Z=2308.532.871birefringence 0.189 @ 532 nm; colourless [1] [38]
Na4Sn4(C2O4)3F6triclinicP1a = 6.0283 b = 8.7916 c = 9.1191 α = 69.486 β = 81.508 γ = 83.017446.413.514birefringence 0.160 @532 nm; colourless; Na 5 or 6 coordinated; Sn type 1: coordinates 2 F and 2 O's from oxalate, which bridges to another Sn type 1) Type 2 Sn has one bond to F, two bonds to Os from an oxalate, and another O from another oxalate. Sn also has weak bonds to other Sn [1] [39]
KSn(C2O4)FmonoclinicP21/ca = 8.0692 b = 9.5398 c = 7.7245 β= 111.600° Z=4552.863.181colourless [40]
K2[SnF2(C2O4)2] · 3H2O [26]
K2[SnF4(C2O4)] · 6.5H2O [26]
K2[Sn2F2(C2O4)6] · 2H2O [26]
K6[Sn2F4(C2O4)5] · 2H2O [26]
NH4Sb2(C2O4)F5birefringence 0.111 @546 nm [1]
(CN4H7)SbC2O4F2(H2O)0.5birefringence 0.126 @546 nm [1]
Na2Sb2(C2O4)F6birefringence 0.188 @546 nm [1]
KSb2C2O4F5monoclinicP21/ca=5.8691 b=6.5124 c=22.178 β=91.893° Z=4847.223.650birefringence 0.170 @532 nm [41] [1]
K2Sb2(C2O4)F6birefringence 0.097 @546 nm [1]
RbSb2(C2O4)F5orthorhombicP212121a=5.9822 b=6.5652 c=22.7919895.14SHG 1.3×KDP; birefringence 0.09 @546 nm [42]
[C(NH2)3]Sb(C2O4)F2·H2Obirefringence 0.323 @546 nm [1]
Cs2Ge(C2O4)2F2·H2O [27]
Cs2GeC2O4F4 [27]
Cs2VO2F(C2O4)
Cs2ZrC2O4F4·2H2O [29]
Cs2Zr2C2O4F8·4H2O [29]
Cs4[Mo2O4 (C2O4)2F2]orthorhombica=10.72 b=9.80 c=7.95 Z=23.98 [34]
Cs2Sb2(C2O4)2F4∙H2Obirefringence 0.325@546 [1]
Lanthanum fluorooxalate ?? [43]
Neodymium fluorooxalate ?? [43]
[TbrF(C2O4)(H2O)2]·2H2O [28]
?[DyF(C2O4)(H2O)2]·2H2ODysprosium fluorooxalateC2/ca=12.0047 b=11.0842 =8.2182 β=129.021° [43] [44]
[HoF(C2O4)(H2O)2]·2H2OHolmium fluorooxalate [43]
[ErF(C2O4)(H2O)2]·2H2Oorthorhombica=11.217 b=13.046 c=9.191 Z=6 [28] [45]
[TmF(C2O4)(H2O)2]·2H2O [28]
[YBF(C2O4)(H2O)2]·2H2O [28]
[LuF(C2O4)(H2O)2]·2H2O [28]
K4Hf(C2O4)3F2·3H2O [29]
K14Hf4(C2O4)5F20·2H2O [29]
K3Hf(C2O42F3· 3H2O [29]
Rb3Hf(C2O42F3· 3H2O [29]
K4Hf(C2O4)2CO3F2·5H2Owater soluble and stable [32]
H2[(C2O4)(OH)3Re·O·Re(OH)3F2]brown
[NH4]2[(C2O4)(OH)3Re·O·Re(OH)3F2]brown
[Co(NH3)6]2[(C2O4)(OH)3Re·O·Re(OH)3F2]3yellowish brown [46]
[Co en3]2[(C2O4)(OH)3Re·O·Re(OH)3F2]3yellowish brown [46]
K2[(C2O4)(OH)3Re·O·Re(OH)3F2]brown
Ni[(C2O4)(OH)3Re·O·Re(OH)3F2]brown [46]
Ba[(C2O4)(OH)3Re·O·Re(OH)3F2]brown [46]
Tl2[(C2O4)(OH)3Re·O·Re(OH)3F2]brown [46]
(UF2)C2O4 · 11/2H2O [47]
(UF)2(C2O4)3 [47]
UF3(H2O)(C2O4)0.5monoclinicC2/ca = 17.246, b = 6.088 c = 8.589 β = 95.43° Z = 8Light green

UIV tricapped trigonal prism coordination (9 fold); each U coordinates 6 bridging fluoride, one water, and two oxalates, which bridge to 3 other U atoms. One oxalate O is in the capped position, and the other 2 O are all on the common face.

 [48]
(H4TREN)[U2F6(C2O4)3]·4H2O

(TREN = tris(2-aminoethyl)amine)

monoclinicP21/ca = 19.1563, b = 8.9531 c = 16.6221 β = 114.633° Z = 42591.42.759green [49]
(H4APPIP)[U2F6(C2O4)3]·4H2O (APPIP = 1,4-bis(3-amino-propyl)piperazine)monoclinicP21/ca = 10.3309 b = 15.564 c = 17.537 β = 95.430° Z=42807.12.675green [49]
Na3[UO2(C2O4)F3]⋅4H2OorthorhombicPnnma=7.9967 b=21.092 c=7.252 Z=41223.23.020yellow [50]
Na3[UO2(C2O4)F3]⋅6H2Otriclinicα°β°γ° [50]
K3[UO2(C2O4)F3]triclinicP1a=9.682 b=10.274 c=10.612 α=104.008° β=97.041° γ=108.774° Z=4946.43.736yellow [50]
K3[UO2(C2O4)2F]⋅3H2OtriclinicP1a=6.6530 b=9.105 c=12.120 α=96.372° β=90.714° γ=93.193° Z=2728.42.902 [50]
Cs[UO2(C2O4)F]⋅H2OmonoclinicP21a=5.4954 b=16.226 c=9.6277 β=98.509° Z=4849.04.130yellow [50]
K2[UO2F2(C2O4)]triclinicP1a=10.981 b=11.038 c=12.629 α=108.00° β=86.79° γ=123.99°1.31yellow [51]
K4[UO2F2(C2O4)2]triclinicP1a=8.768 b=8.777 c=14.857 α=101.58° β=114.27° γ=85.27°4.16yellow [51]
K2[(UO2)2F4(C2O4)]monoclinica=10.792 b=12.028 c=10.615 β=136.88°2.92yellow; oxalate is tetradentate, bridging 2 U [51]
Rb2[UO2F2(C2O4)]yellow [51]
Rb4[UO2F2(C2O4)2]yellow [51]
Rb2[(UO2)2F4(C2O4)]yellow [51]

References

  1. 1 2 3 4 5 6 7 8 9 10 11 Ji, Sen; Kang, Lei; Han, Yanyang; Liu, Shanshan; Liu, Ye; Yang, Xin; Feng, Kai (December 2024). "A novel sodium manganese fluorooxalate crystal Na2Mn2(C2O4)2.5F·2H2O: Synthesis, structure, optical and thermal properties" . Journal of Solid State Chemistry. 340: 125031. doi:10.1016/j.jssc.2024.125031.{{cite journal}}: CS1 maint: article number as page number (link)
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  4. ↑ Tian, Shengfeng; Qi, Li; Yoshio, Masaki; Wang, Hongyu (June 2014). "Tetramethylammonium difluoro(oxalato)borate dissolved in ethylene/propylene carbonates as electrolytes for electrochemical capacitors" . Journal of Power Sources. 256: 404–409. Bibcode:2014JPS...256..404T. doi:10.1016/j.jpowsour.2014.01.101.
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  6. 1 2 3 4 5 6 7 8 Kang, Colin S. M.; Hutt, Oliver E.; Pringle, Jennifer M. (2022-07-05). "Halide-Free Synthesis of New Difluoro(oxalato)borate [DFOB] − -Based Ionic Liquids and Organic Ionic Plastic Crystals". ChemPhysChem. 23 (13): e202200115. doi:10.1002/cphc.202200115. ISSN   1439-4235. PMC   9401595 . PMID   35451216.{{cite journal}}: CS1 maint: article number as page number (link)
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