An oxalate chloride or oxalato chloride is a mixed anion compound contains both oxalate and chloride anions .
Related compounds include oxalate fluorides [ 1] and oxalate bromides .[ 2]
Production
Oxalate chlorides may be produced by treating an oxalate salt with concentrated hydrochloric acid, or with a metal oxide dissolved in oxalic acid and hydrochloric acid solutions that are evaporated.[ 3]
List
name
formula
crystal
space group
cell
volume
density
comment
ref
Novgorodovaite
Ca2 (C2 O4 )Cl2 •2H2 O
monoclinic
I 2/m
a=6.936 b=7.382 c=7.443 β=94.3°
loses water over 205°C; refract: α=1.500 β=1.545 γ=1.568 2V=71° (−)
[ 4] [ 5] [ 6]
Ca2 (C2 O4 )Cl2 •7H2 O
triclinic
P 1
a = 7.3928 b = 8.9925 c = 10.484 α = 84.070 β = 70.95 γ = 88.545°
655.3
looses water at 25°C to 2H2 O; refract: α=1.571 β=1.648 γ=1.718 2V=87° (−)
[ 4] [ 7]
Ca4 (C2 O4 )3 Cl2 •8H2 O
dubious
[ 4]
octakis(ethyl(dimethyl)ammonium) dodecakis(μ-oxalato)-tetrachloro-tetra-chromium-tetra-manganese
[NH(CH3 )2 (C2 H5 )]8 [Mn4 Cl4 Cr4 (C2 O4 )12 ]
monoclinic
P 21
a =13.8321 b =17.1042 c =20.4209 β =91.874°
[ 8]
octakis(diethyl(methyl)ammonium) dodecakis(μ-oxalato)-tetrachloro-tetra-chromium-tetra-manganese
[NH(CH3 )(C2 H5 )2 ]8 [Mn4 Cl4 Cr4 (C2 O4 )12 ]
monoclinic
P 21
a =14.1863 b =17.3479 c =20.4140 β =91.937°
[ 8]
DABCO=1,4-diazabicyclo[2.2.2]octane;
(DABCO-H+ )2 (DABCO-2H2+ )[MnII (CH3 OH)(Cl− )CrIII (oxalate)3 ]2− 2 (CH3 OH)
triclinic
P 1
a =8.093 b =9.070 c =19.574 α =83.471° β =89.875° γ =86.765°
[ 9]
tetrakis(methylammonium) tetrakis(μ-oxalato)-octachloro-tetra-iron(iii) pentahydrate
(MeNH3 )2 [Fe2 (ox)2 Cl4 ]·2.5H2 O
monoclinic
P 21 /c
a 10.7832 b 13.913 c 13.0578 β 104.060°
[ 10]
methylammonium (μ-hydroxo)-bis(μ-oxalato)-dichloro-di-iron(iii) trihydrate
MeNH3 [Fe2 (OH)(ox)2 Cl2 ]·2H2 O
monoclinic
Cc
a =8.945 b =14.936 c =12.408 β =108.531°
[ 10]
methylammonium oxonium bis(μ-oxalato)-(μ-oxo)-dichloro-di-iron(iii) dihydrate
(H3 O)(MeNH3 )[Fe2 O(ox)2 Cl2 ]·3H2 O
orthorhombic
Fdd 2
a =14.914 b =23.507 c =9.261
[ 10]
DMF = dimethylformamide
Fe2 (C2 O4 )Cl4 (DMF)4
triclinic
P 1
a =8.3919 b =8.7834 c =11.2881 α =70.248° β =71.993° γ =64.423°
[ 11]
(dimim)2 [Fe2 Cl4 (μ-ox)]
ionic liquid
[ 12]
L2 =1,4-bis(imidazol-1-ylmethyl)benzene
bis(1,1'-(1,4-Phenylenebis(methylene))bis-1H-imidazol-3-ium) (μ2 -oxalato)-tetrachloro-bis(oxalato)-di-iron(iii)
(H2 -L2 )2 {Fe2 (C2 O4 )3 Cl4 }
triclinic
P 1
a =10.6758 b =10.7457 c =10.8774 α =113.219° β =109.138° γ =99.294° Z=1
1020.8
1.624
emerald
[ 13]
tetramelaminium trioxalatoferrate(III) chloride dihydrate
(C3 H7 N6 )4 {Fe(C2 O4 )3 }Cl·2H2 O
monoclinic
P 21 /c
a =11.597 b =22.299 c =13.655 β =94.344° Z=4
3521
1.698
green
[ 14]
methylammonium (μ-aqua)-tris(μ-chloro)-(μ-oxalato)-iron(iii)-potassium
K(MeNH3 )[Fe(ox)Cl3 (H2 O)
monoclinic
P 21 /m
a =8.725 b =7.508 c =9.026 β =112.421°
[ 10]
diethylmethylammonium
[NH(CH3 )(C2 H5 )2 ][FeCl2 (C2 O4 )]
monoclinic
P 21 /c
a=8.5125 b=10.775 c=14.9703 β =104.798° Z=4
1327.6
1.516
yellow; proton conductor
[ 15]
bis(Tetramethylammonium) bis(μ2 -oxalato)-tetrachloro-di-iron(iii)
Me4 N[FeIII (ox)Cl2 ]
monoclinic
P 21 /c
a =7.9441 b =8.6093 c =17.8251 β =91.869
[ 16]
hexakis(Triethylammonium) hexakis(μ2 -oxalato)-dodecachloro-hexa-iron(iii)
Et3 NH[FeIII (ox)Cl2 ]
triclinic
P 1
a =10.9609 b =14.4602 c =14.5780 α =85.006° β =78.845° γ =83.0191
[ 16]
Triethylammonium (μ2 -oxalato)-dichloro-iron(iii)
Et3 NH[FeIII (ox)Cl2 ]
orthorhombic
Fdd 2
a =13.5878 b =37.972 c =10.8210
[ 16]
bis(Tetra-n-butylammonium) bis(μ2 -oxalato)-tetrachloro-di-iron(iii)
n -Bu4 N[FeIII (ox)Cl2 ]
monoclinic
P 21 /c
a =8.8836 b =15.1939 c =17.968 β =91.556°
[ 16]
[Fe(oxalato)Cl2 ]3 (3,5-dimethylpyrazole)2 (3,5- dimethylpyrazolium)2
monoclinic
C 2/c
a=19.527 b=11.867 c=19.429 β =115.66° Z=4
4058.20
1.684
green
[ 17]
BETS = Bis(ethylenedithio)tetraselenafulvalene
κ-BETS2 [FeIII (C2 O4 )Cl2 ]
black; metallic;
[ 18]
bis(2-(5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithiin-1-ium) bis(μ-oxalato)-tetrachloro-di-iron(iii)
[BEDT-TTF][Fe(C2 O4 )Cl2 ]
triclinic
P 1
a =8.896 b =11.401 c =11.427 α =112.062° β =103.775° γ =100.328°
[ 19]
BEDT-TTF = Bis(ethylenedithio)tetrathiafulvalene
(BEDT-TTF)[Fe(C2 O4 )Cl2 ](CH2 Cl2 )
monoclinic
P 21 /c
a =8.858 b =11.012 c =14.932 β =103.39°
[ 20]
tris(ethylenediamine)cobalt(III)chloride oxalate trihydrate
[Co(en)3 ]Cl(C2 O4 )·3H2 O
monoclinic
C 2/c
a = 19.932 b = 9.3344 c = 19.088 β = 96.846° Z = 8
[ 21]
dpyam=di-2-pyridylamine; (μ2 -Oxalato)-bis(di-2-pyridylamine)-dichloro-di-copper(ii)
Cu2 (dpyam)2 (μ-C2 O4 )(Cl)2
triclinic
P 1
a =7.4122 b =8.6586 c =9.8002 α =87.900° β =72.022° γ =71.845°
[ 22]
L = 3,5-dimethyl-1H -pyrazole
Cu2 (C2 O4 )(L)2 Cl2 (MeOH)2
triclinic
P 1
a =7.244 b =8.039 c =8.848 α =92.16° β =92.73° γ =96.21°
[ 23]
bpy=bipyridine
[Fe(bpy)3 ]2 [NbO(C2 O4 )3 ]Cl·11H2 O
[ 24]
[Fe(bpy)3 ]2 [NbO(2 O4 )3 ]Cl·12H2 O
orthorhombic
P 21 21 21
a=14.975 b=21.708 c=22.351 Z=4
7266
1.530
dark red
[ 24]
[Co(bpy)3 ]2 [NbO(C2 O4 )3 ]Cl·11H2 O
monoclinic
P 21 /c
a=23.548 b=13.631 c=22.812 β =101.04
7187
1.536
orange red
[ 24]
[Co(bpy)3 ]2 [NbO(C2 O4 )3 ]Cl·12H2 O
orthorhombic
P 21 21 21
a=15.103 b=22.075 c=22.386 Z=4
7463
1.495
brown
[ 24]
[Ni(bpy)3 ]2 [NbO(C2 O4 )3 ]Cl·11H2 O
monoclinic
P 21 /c
a=23.875 b=13.265 c=23.115 β =101.69 Z=4
7169
1.539
pink
[ 24]
[Ni(bpy)3 ]2 [NbO(C2 O4 )3 ]Cl·12H2 O
orthorhombic
P 21 21 21
15.058 b=22.039 c=22.398 Z=4
7433
1.500
dark pink
[ 24]
[Cu(bpy)3 ]2 [NbO(C2 O4 )3 ]Cl·12H2 O
orthorhombic
P 21 21 21
a=15.035 b=22.267 c=22.538 Z=4
7545
1.487
blue
[ 24]
[Zn(bpy)3 ]2 [NbO(C2 O4 )3 ]Cl·11H2 O
monoclinic
P 21 /c
24.070 b=13.332 c=23.168 β=102.19 Z=4
7267
1.530
pink
[ 24]
[Zn(bpy)3 ]2 [NbO(C2 O4 )3 ]Cl·12H2 O
[ 24]
tris(Tetraethylammonium) tetrakis(μ3 -sulfido)-(oxalato-O,O')-trichloro-cyano-tri-iron-molybdenum
(Et4 N)5 {[C2 O4 )MoFe3 S4 Cl2 ]2 (μ-CN)(μ-S)}
monoclinic
P 21 /n
a =10.331 b =22.580 c =19.083 β =91.97°
double cubane structure
[ 25]
(μ2 -Oxalato)-dichloro-bis(η6 -p-cymene)-di-ruthenium
[Ru2 (μ-η4 -C2 O4 )Cl2 (η6 -p-Pri C6 H4 Me)2 ]
monoclinic
P 21 /n
a =7.571 b =8.998 c =16.528 β =95.52° Z=2
1120.73
yellow
[ 26]
chloro-(oxalato)-tris(pyridine)-rhodium
mer -[Rh(C2 O4 )Cl(py)3 ]
orthorhombic
P 21 21 21
a =9.9999 b =12.0930 c =14.9368 Z=4
1806.2
1.705
yellow
[ 27]
CHLOROPENTAAMMINECHROMIUM(III) BIS(OXALATO)PALLADATE
[Cr(NH3 )5 Cl][Pd(C2 O4 )2 ]
triclinic
a = 3.225 b = 10.290 c = 11.390 α = 116.5° β = 97.9° γ = 91.2°
334.5
[ 28]
C(NH2 )3 Cd(C2 O4 )Cl(H2 O)·H2 O
triclinic
P 1
a =6.8136 b =7.4890 c =10.0515 α =84.082° β =77.806° γ =88.813°
band gap 3.76 eV
[ 29]
SnC2 O4 Cl2
[ 30]
SnC2 O4 Cl2 . CuBr2 1/4EtOH
green
[ 30]
SnC2 O4 Cl2 . CuCl2 . H2 O
green
[ 30]
SnC2 O4 Cl2 . CoBr2 1/8EtOH
rose colour
[ 30]
(Et4 N)2 C2 O4 . SnCl2 F2 . 2H2 O:
white
[ 30]
(Me4 N)2 Sn(C2 O4 )Cl2
white
[ 30]
(Et4 N)2 Sn(C2 O4 )Cl2 .(Et4 N)2 C2 O4 (SnCl4 )2 . EtOH
white
[ 30]
Sn(C2 O4 )2 . 2[SnCl4 . (Pyridine)2 ]
white
[ 30]
(Et4 N)2 SnCl6 . (Et4 N)2 C2 O4 . 2SnC2 O4 (OH)2
white
[ 30]
(NH4 )2 Sb(C2 O4 )Cl3
orthorhombic
P 21 21 21
a=8.6961 b=8.7844 c=13.5956 Z=4
1038.57
2.253
[ 31]
K2 Sb(C2 O4 )Cl3
orthorhombic
P 21 21 21
a=8.3966 b=8.6023 c=13,6342 Z=4
984.80
2.660
[ 31]
Rb2 Sb(C2 O4 )Cl3
orthorhombic
P 21 21 21
a=8.6769 b=8.8485 c=13.8014 Z=4
1059.64
3.053
birefringence 0.22@546 nm;NLO 2.1 × KH2 PO4
[ 31]
Ba2 Mn2 Cl2 (C2 O4 )3 ·4H2 O
monoclinic
C 2/c
a =22.916 b =8.248 c =9.904 β =99.53°
[ 32]
Ba2 Fe2 Cl2 (C2 O4 )3 ·4H2 O
monoclinic
C 2/c
a =22.798 b =8.297 c =9.849 β =99.90°
[ 32]
Ba2 Co2 Cl2 (C2 O4 )3 ·4H2 O
monoclinic
C 2/c
a =22.675 b =8.230 c =9.757 β =100.00°
purple
[ 33] [ 32]
BaCd(C2 O4 )1.5 Cl(H2 O)2
monoclinic
C 2/c
a =23.101 b =8.253 c =10.040 β 99.14°
band gap 4.53 eV
[ 29]
La(C2 O4 )Cl
monoclinic
P 21 /n
a =8.489 b =16.19 c =5.880 β =104.14°
[ 34] [ 35]
La(C2 O4 )Cl·3H2 O
[ 36]
Ce(C2 O4 )Cl
[ 1]
Ce(C2 O4 )Cl·3H2 O
[ 36]
Pr(C2 O4 )Cl·3H2 O
stable to 163°C
[ 36] [ 1]
Nd(C2 O4 )Cl·3H2 O
stable to 167°C; dec 510° to NdOCl
[ 36] [ 1] [ 37]
Sm(C2 O4 )Cl·3H2 O
stable to 174°C; dec at 347° to EuC2 O4
[ 36] [ 1]
Eu(C2 O4 )Cl·3H2 O
stable to 178°C
[ 36] [ 1]
Gd(C2 O4 )Cl·3H2 O
[ 36] [ 38]
(Et4 N)2 Sn(C2 O4 )Cl2 . (Et4 N)2 C2 O4 (SnCl4 )2 . EtOH
[ 30]
[(Me4 N)2 C2 O4 SnCl4 ]2 . [(Me4 N)2 Sn(C2 O4 )2 Cl2 ]2 . Sn(WO4 )2
[ 30]
[Pt(HC2 O4 )Cl3 ]2−
[ 39]
[Pt(HC2 O4 )(C2 O4 )Cl]2−
[ 39]
K2 [Pt(C2 O4 )Cl2 ]·H2 O
triclinic
P 1
a=7.136 b=7.308 c=10.130 α=86.75° β=74.58° γ=54.28° Z=2
457.7
3.27
[ 40] [ 39]
[Pt(NH3 )5 Cl][Cr(C2 O4 )3 ] · 4H2 O
orthorhombic
Pccn
a =38.901 b =13.7267 c =14.9141
[ 41]
[Pt(NH3 )5 Cl][Fe(C2 O4 )3 ] · 4H2 O
orthorhombic
Pccn
a =39.0123 b =13.7232 c =14.8990
[ 41]
[Pt(NH3 )5 Cl][Co(C2 O4 )3 ] · 2H2 O
monoclinic
P 21
a =8.5158 b =12.6409 c =8.5726 β =105.000°
[ 41]
lead chloride oxalate
Pb2 Cl2 (C2 O4 )
monoclinic
C 2/m
a=5.9411 b=5.8714 c=9.4212 β=95.232° Z=2
327.26
5.82
dec 350°C to Pb, Pb5 O2 Cl6 and Pb3 O2 Cl2
[ 42]
Th4 Cl4 (C2 O4 )6 •20H2 O
Plutonium(III) oxalato chloride
?Pu(C2 O4 )Cl·3H2 O
blue; biaxial (−)
[ 43]
Am(C2 O4 )Cl·3H2 O
monoclinic
P 21 /n
a =5.852 b =15.823 c =8.351 β =104.243°
[ 44]
References
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Salts and covalent derivatives of the
chloride ion