An oxalate fluoride is a mixed anion compound contains both oxalate and fluoride anions. Many of these compounds have high birefringence. [1]
With nonmetals, some are related to the oxalatophosphates and oxalatoborates with the addition of fluoride.
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]
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]
formula | name | crystal | space group | cell | volume | density | comment | ref |
---|---|---|---|---|---|---|---|---|
N(CH3)4BF2C2O4 | tetramethylammonium difluoro(oxalato)borate | [4] | ||||||
N(CH2CH3)4BF2C2O4 | tetraethylammonium difluoro(oxalato)borate | [5] | ||||||
triethylmethylammonium difluoro(oxalato)borate | melt 15 °C; white | [6] | ||||||
N(-CH2CH2CH2CH2-)(CH2CH2CH3)(CH3)BF2C2O4 | N-Propyl-N-Methylpyrrolidinium Difluoro(oxalato)borate (Py13DFOB) | melt 3.21 °C | [7] | |||||
N(-CH2CH2CH2CH2-)(CH2CH2CH2CH3)(CH3)BF2C2O4 | N-butyl-N-methylpyrrolidinium difluoro(oxalato)borate (Py14DFOB) | melt −5 °C | [8] | |||||
N(-CH2CH2CH2CH2-)(CH2CH2CH2CH2CH3)(CH3)BF2C2O4 | N-pentyl-N-methylpyrrolidinium difluoro(oxalato)borate (Py15DFOB) | glass transition −74 °C | [8] | |||||
N(-CH2CH2CH2CH2-)(CH2CH2CH2CH2CH2CH3)(CH3)BF2C2O4 | N-hexyl-N-methylpyrrolidinium difluoro(oxalato)borate (Py16DFOB) | melt 31 °C | [8] | |||||
1-ethyl-1-methylpyrrolidinium difluoro(oxalato)borate | melt 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)borate | ionic liquid, gl;ass transition -70 °C | [9] | ||||||
N-propyl-N-methylpiperidinium difluoro(oxalate)borate | ionic liquid | [9] | ||||||
LiBF2C2O4 | lithium difluoro(oxalato)borate | orthorhombic | Cmcm | a = 6.2623 b = 11.437 c = 6.3002 Z = 4 | 451.22 | [10] | ||
LiBF2C2O4·2H2O | lithium difluoro(oxalato)borate dihydrate | monoclinic | P21/c | a = 9.5580 b = 12.7162 c = 5.4387 Z = 4 | 634.63 | [10] | ||
NaBF2C2O4 | sodium difluoro(oxalato)borate | tetragonal | I41md | a=7.7316 c=8.5343 | 510.16 | [11] | ||
Na(C2BF2O4)(CH3CN)2 | orthorhombic | Pnma | a=11.6932 b = 14.1254 c = 6.5130 Z=4 | 1075.76 | B tertrahedral coordination by 2 F and twice by -OCCO- | [12] | ||
Na2Mn2(C2O4)2.5F·2H2O | triclinic | P1 | a =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)2F2.3H2O | soluble | [2] | ||||||
triethylmethylphosphonium difluoro(oxalato)borate | melt 9 °C; white | [6] | ||||||
diethylisobutylmethylphosphonium difluoro(oxalato)borate | melt 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)2F2.3H2O | soluble | [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]·5H2O | green | [17] | ||||||
[NH4]3[Cr(C2O4)F4]·4H2O | [17] | |||||||
PyH[Cr(H2O)2F2(C2O4)] Py=pyridine | green | [16] | ||||||
enH2[Cr(H2O)2F2(C2O4)]2. 2H2O en=ethylenediamine | green | [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)]. H2O | green | [16] | ||||||
Na3[Cr(C2O4)2F2]·5H2O | green | [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]·5H2O | green | [17] | ||||||
K3[Cr(C2O4)F4]·3H2O | [17] | |||||||
[NH4][MnF(C2O4)] | pale pink | [18] | ||||||
[NH4]2Mn(C2O4)F3 | pink; CAS 94138-08-6 | [19] | ||||||
pyH[MnF2(C2O4)(H2O)2] | monoclinic | I2/a | a = 7.2260 b = 15.2398 c = 9.916 β = 98.22° Z = 4 | Octahedral coordination on Mn, Cis-F opposite oxalate. 2 aqua is trans | [20] | |||
Na[MnF(C2O4)]·2H2O | pale pink | [18] | ||||||
Na2Mn(C2O4)F3 | pink; CAS 94138-06-4 | [19] | ||||||
Na2Mn2(C2O4)2.5F·2H2O | triclinic | P1 | a = 7.9129 b = 8.8497 c = 8.9252 α = 74.623oβ = 72.361 oγ = 78.193 o, Z = 2 | birefringence 0.064@550 nm; light yellow | [1] | |||
K[MnF(C2O4)] | pale pink | [18] | ||||||
K2Mn(C2O4)F3 | pink; CAS 4138-07-5; | [19] | ||||||
Na2Fe(C2O4)F2 | monoclinic | C12/c1 | a=15.8349 b=5.962 c=12.2784 β=111.968° Z=8 | 1075.0 | 2.816 | green | [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 monohydrate | orthorhombic | Pca21 | a=10.816 b=16.929 c=19.491 | [23] | |||
(imidH)2[Fe2(C2O4)F6] | orthorhombic | Pban | a=9.143 b=20.837 c=3.890 Z=2 | ladder, oxalate rungs | [24] | |||
[Fe2(C2O4)F4(DMSO)4] | monoclinic | P21/n | a=7.259 b=11.409 c=13.374 β=97.26° Z=2 | dimer, oxalate bridged | [24] | |||
Na3[Fe(C2O4)2F2]·4H2O | light green | [22] | ||||||
KFe(C2O4)F | orthorhombic | Cmc21 | a=7.7633 b=11.8767 c=10.4206 | red or orange | [25] | |||
K[Fe(C2O4)F2]·2H2O | yellowish green | [22] | ||||||
K2[Fe(C2O4)2F]·3H2O | [22] | |||||||
K3[Fe(C2O4)2F2]·2.8H2O | light green | [22] | ||||||
Co(NH3)6Al(C2O4)2F2.3H2O | orange yellow; insoluble | [2] | ||||||
[Co(NH3)6][Cr(C2O4)2F2]·6H2O | pale green | [17] | ||||||
[Co(NH3)6][Cr(C2O4)F4]·4H2O | pale green | [17] | ||||||
[Co(NH3)6][Cr(H2O)2F2(C2O4)]3. 2H2O | yellowish-green; sparingly soluble | [16] | ||||||
[Co(en)3][Cr(C2O4)2F2]·7H2O | pale green | [17] | ||||||
[Co(en)3][Cr(C2O4)F4]·3H2O | pale green | [17] | ||||||
[Co(en)3][Cr(H2O)2F2(C2O4)]3. 3H2O | yellowish green | [16] | ||||||
[Co(NH3)6][Fe(C2O4)F2]3·6H2O | orange yellow | [22] | ||||||
[Co(en)3][Fe(C2O4)F2]3 | orange yellow | [22] | ||||||
[Co(NH3)6]2[Fe(C2O4)2F]3·9H2O | orange yellow | [22] | ||||||
[Co(en)3]2[Fe(C2O4)2F]3·4H2O | orange yellow | [22] | ||||||
[Co(NH3)6][Ga(C2O4)2F2].3H2O | insoluble | [2] | ||||||
Ni[Cr(H2O)2F2(C2O4)]2. 2H2O | green | [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] | orthorhombic | a=1065 b=8.88 c=8.09 Z=2 | 3.52 | [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] | monoclinic | P21/c | a=7.6943 b=9.8135 c=7.7252 β=109.648 Z=4 | 549.35 | 3.300 | [36] | ||
Rb2[InF3(C2O4)H2O] | monoclinic | P21/c | a=7.8308 b=9.9671 c=7.9327 β=111.266 Z=4 | 576.98 | 3.676 | [36] | ||
[Co(NH3)6][In(C2O4)2F2].2H2O | [35] | |||||||
[Sn(C2O4)F-][NH4+] | monoclinic | P21/c | a = 8.2736 b = 9.6386 c = 7.7473 β = 111.229° Z = 4 | [37] | ||||
NaSnC2O4F·H2O | triclinic | P1 | a = 5.9880 b = 7.2468 c = 8.2925 α = 111.020°β = 107.986° γ = 96.873° Z=2 | 308.53 | 2.871 | birefringence 0.189 @ 532 nm; colourless | [1] [38] | |
Na4Sn4(C2O4)3F6 | triclinic | P1 | a = 6.0283 b = 8.7916 c = 9.1191 α = 69.486 β = 81.508 γ = 83.017 | 446.41 | 3.514 | birefringence 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)F | monoclinic | P21/c | a = 8.0692 b = 9.5398 c = 7.7245 β= 111.600° Z=4 | 552.86 | 3.181 | colourless | [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)F5 | birefringence 0.111 @546 nm | [1] | ||||||
(CN4H7)SbC2O4F2(H2O)0.5 | birefringence 0.126 @546 nm | [1] | ||||||
Na2Sb2(C2O4)F6 | birefringence 0.188 @546 nm | [1] | ||||||
KSb2C2O4F5 | monoclinic | P21/c | a=5.8691 b=6.5124 c=22.178 β=91.893° Z=4 | 847.22 | 3.650 | birefringence 0.170 @532 nm | [41] [1] | |
K2Sb2(C2O4)F6 | birefringence 0.097 @546 nm | [1] | ||||||
RbSb2(C2O4)F5 | orthorhombic | P212121 | a=5.9822 b=6.5652 c=22.7919 | 895.14 | SHG 1.3×KDP; birefringence 0.09 @546 nm | [42] | ||
[C(NH2)3]Sb(C2O4)F2·H2O | birefringence 0.323 @546 nm | [1] | ||||||
Cs2Ge(C2O4)2F2·H2O | [27] | |||||||
Cs2GeC2O4F4 | [27] | |||||||
Cs2VO2F(C2O4) | ||||||||
Cs2ZrC2O4F4·2H2O | [29] | |||||||
Cs2Zr2C2O4F8·4H2O | [29] | |||||||
Cs4[Mo2O4 (C2O4)2F2] | orthorhombic | a=10.72 b=9.80 c=7.95 Z=2 | 3.98 | [34] | ||||
Cs2Sb2(C2O4)2F4∙H2O | birefringence 0.325@546 | [1] | ||||||
Lanthanum fluorooxalate ?? | [43] | |||||||
Neodymium fluorooxalate ?? | [43] | |||||||
[TbrF(C2O4)(H2O)2]·2H2O | [28] | |||||||
?[DyF(C2O4)(H2O)2]·2H2O | Dysprosium fluorooxalate | C2/c | a=12.0047 b=11.0842 =8.2182 β=129.021° | [43] [44] | ||||
[HoF(C2O4)(H2O)2]·2H2O | Holmium fluorooxalate | [43] | ||||||
[ErF(C2O4)(H2O)2]·2H2O | orthorhombic | a=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)2CO3F2·5H2O | water 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]3 | yellowish brown | [46] | ||||||
[Co en3]2[(C2O4)(OH)3Re·O·Re(OH)3F2]3 | yellowish 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)0.5 | monoclinic | C2/c | a = 17.246, b = 6.088 c = 8.589 β = 95.43° Z = 8 | Light 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) | monoclinic | P21/c | a = 19.1563, b = 8.9531 c = 16.6221 β = 114.633° Z = 4 | 2591.4 | 2.759 | green | [49] | |
(H4APPIP)[U2F6(C2O4)3]·4H2O (APPIP = 1,4-bis(3-amino-propyl)piperazine) | monoclinic | P21/c | a = 10.3309 b = 15.564 c = 17.537 β = 95.430° Z=4 | 2807.1 | 2.675 | green | [49] | |
Na3[UO2(C2O4)F3]⋅4H2O | orthorhombic | Pnnm | a=7.9967 b=21.092 c=7.252 Z=4 | 1223.2 | 3.020 | yellow | [50] | |
Na3[UO2(C2O4)F3]⋅6H2O | triclinic | α°β°γ° | [50] | |||||
K3[UO2(C2O4)F3] | triclinic | P1 | a=9.682 b=10.274 c=10.612 α=104.008° β=97.041° γ=108.774° Z=4 | 946.4 | 3.736 | yellow | [50] | |
K3[UO2(C2O4)2F]⋅3H2O | triclinic | P1 | a=6.6530 b=9.105 c=12.120 α=96.372° β=90.714° γ=93.193° Z=2 | 728.4 | 2.902 | [50] | ||
Cs[UO2(C2O4)F]⋅H2O | monoclinic | P21 | a=5.4954 b=16.226 c=9.6277 β=98.509° Z=4 | 849.0 | 4.130 | yellow | [50] | |
K2[UO2F2(C2O4)] | triclinic | P1 | a=10.981 b=11.038 c=12.629 α=108.00° β=86.79° γ=123.99° | 1.31 | yellow | [51] | ||
K4[UO2F2(C2O4)2] | triclinic | P1 | a=8.768 b=8.777 c=14.857 α=101.58° β=114.27° γ=85.27° | 4.16 | yellow | [51] | ||
K2[(UO2)2F4(C2O4)] | monoclinic | a=10.792 b=12.028 c=10.615 β=136.88° | 2.92 | yellow; oxalate is tetradentate, bridging 2 U | [51] | |||
Rb2[UO2F2(C2O4)] | yellow | [51] | ||||||
Rb4[UO2F2(C2O4)2] | yellow | [51] | ||||||
Rb2[(UO2)2F4(C2O4)] | yellow | [51] |