Oxalate chloride

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An oxalate chloride or oxalato chloride is a mixed anion compound contains both oxalate and chloride anions.

Contents

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

nameformulacrystalspace groupcellvolumedensitycommentref
Novgorodovaite Ca2(C2O4)Cl2•2H2OmonoclinicI2/ma=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(C2O4)Cl2•7H2OtriclinicP1a = 7.3928 b = 8.9925 c = 10.484 α = 84.070 β = 70.95 γ = 88.545°655.3looses water at 25°C to 2H2O; refract: α=1.571 β=1.648 γ=1.718 2V=87° (−) [4] [7]
Ca4(C2O4)3Cl2•8H2Odubious [4]
octakis(ethyl(dimethyl)ammonium) dodecakis(μ-oxalato)-tetrachloro-tetra-chromium-tetra-manganese[NH(CH3)2(C2H5)]8[Mn4Cl4Cr4(C2O4)12]monoclinicP21a=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)(C2H5)2]8[Mn4Cl4Cr4(C2O4)12]monoclinicP21a=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(CH3OH)(Cl−)CrIII(oxalate)3]2−2(CH3OH)triclinicP1a=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)2Cl4]·2.5H2OmonoclinicP21/ca 10.7832 b 13.913 c 13.0578 β 104.060° [10]
methylammonium (μ-hydroxo)-bis(μ-oxalato)-dichloro-di-iron(iii) trihydrateMeNH3[Fe2(OH)(ox)2Cl2]·2H2OmonoclinicCca=8.945 b=14.936 c=12.408 β=108.531° [10]
methylammonium oxonium bis(μ-oxalato)-(μ-oxo)-dichloro-di-iron(iii) dihydrate(H3O)(MeNH3)[Fe2O(ox)2Cl2]·3H2OorthorhombicFdd2a=14.914 b=23.507 c=9.261 [10]
DMF = dimethylformamideFe2(C2O4)Cl4(DMF)4triclinicP1a=8.3919 b=8.7834 c=11.2881 α=70.248° β=71.993° γ=64.423° [11]
(dimim)2[Fe2Cl4(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(C2O4)3Cl4}triclinicP1a=10.6758 b=10.7457 c=10.8774 α=113.219° β=109.138° γ=99.294° Z=11020.81.624emerald [13]
tetramelaminium trioxalatoferrate(III) chloride dihydrate(C3H7N6)4{Fe(C2O4)3}Cl·2H2OmonoclinicP21/ca=11.597 b=22.299 c=13.655 β=94.344° Z=435211.698green [14]
methylammonium (μ-aqua)-tris(μ-chloro)-(μ-oxalato)-iron(iii)-potassiumK(MeNH3)[Fe(ox)Cl3(H2O)monoclinicP21/ma=8.725 b=7.508 c=9.026 β=112.421° [10]
diethylmethylammonium[NH(CH3)(C2H5)2][FeCl2(C2O4)]monoclinicP21/ca=8.5125 b=10.775 c=14.9703 β=104.798° Z=41327.61.516yellow; proton conductor [15]
bis(Tetramethylammonium) bis(μ2-oxalato)-tetrachloro-di-iron(iii)Me4N[FeIII(ox)Cl2]monoclinicP21/ca=7.9441 b=8.6093 c=17.8251 β=91.869 [16]
hexakis(Triethylammonium) hexakis(μ2-oxalato)-dodecachloro-hexa-iron(iii)Et3NH[FeIII(ox)Cl2]triclinicP1a=10.9609 b=14.4602 c=14.5780 α=85.006° β=78.845° γ=83.0191 [16]
Triethylammonium (μ2-oxalato)-dichloro-iron(iii)Et3NH[FeIII(ox)Cl2]orthorhombicFdd2a=13.5878 b=37.972 c=10.8210 [16]
bis(Tetra-n-butylammonium) bis(μ2-oxalato)-tetrachloro-di-iron(iii)n-Bu4N[FeIII(ox)Cl2]monoclinicP21/ca=8.8836 b=15.1939 c=17.968 β=91.556° [16]
[Fe(oxalato)Cl2]3(3,5-dimethylpyrazole)2(3,5- dimethylpyrazolium)2monoclinicC2/ca=19.527 b=11.867 c=19.429 β=115.66° Z=44058.201.684green [17]
BETS = Bis(ethylenedithio)tetraselenafulvaleneκ-BETS2[FeIII(C2O4)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(C2O4)Cl2]triclinicP1a=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(C2O4)Cl2](CH2Cl2)monoclinicP21/ca=8.858 b=11.012 c=14.932 β=103.39° [20]
tris(ethylenediamine)cobalt(III)chloride oxalate trihydrate[Co(en)3]Cl(C2O4)·3H2OmonoclinicC2/ca = 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-C2O4)(Cl)2triclinicP1a=7.4122 b=8.6586 c=9.8002 α=87.900° β=72.022° γ=71.845° [22]
L = 3,5-dimethyl-1H-pyrazoleCu2(C2O4)(L)2Cl2(MeOH)2triclinicP1a=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(C2O4)3]Cl·11H2O [24]
[Fe(bpy)3]2[NbO(2O4)3]Cl·12H2OorthorhombicP212121a=14.975 b=21.708 c=22.351 Z=472661.530dark red [24]
[Co(bpy)3]2[NbO(C2O4)3]Cl·11H2OmonoclinicP21/ca=23.548 b=13.631 c=22.812 β=101.0471871.536orange red [24]
[Co(bpy)3]2[NbO(C2O4)3]Cl·12H2OorthorhombicP212121a=15.103 b=22.075 c=22.386 Z=474631.495brown [24]
[Ni(bpy)3]2[NbO(C2O4)3]Cl·11H2OmonoclinicP21/ca=23.875 b=13.265 c=23.115 β=101.69 Z=471691.539pink [24]
[Ni(bpy)3]2[NbO(C2O4)3]Cl·12H2OorthorhombicP21212115.058 b=22.039 c=22.398 Z=474331.500dark pink [24]
[Cu(bpy)3]2[NbO(C2O4)3]Cl·12H2OorthorhombicP212121a=15.035 b=22.267 c=22.538 Z=475451.487blue [24]
[Zn(bpy)3]2[NbO(C2O4)3]Cl·11H2OmonoclinicP21/c24.070 b=13.332 c=23.168 β=102.19 Z=472671.530pink [24]
[Zn(bpy)3]2[NbO(C2O4)3]Cl·12H2O [24]
tris(Tetraethylammonium) tetrakis(μ3-sulfido)-(oxalato-O,O')-trichloro-cyano-tri-iron-molybdenum(Et4N)5{[C2O4)MoFe3S4Cl2]2(μ-CN)(μ-S)}monoclinicP21/na=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-C2O4)Cl2(η6-p-PriC6H4Me)2]monoclinicP21/na=7.571 b=8.998 c=16.528 β=95.52° Z=21120.73yellow [26]
chloro-(oxalato)-tris(pyridine)-rhodiummer-[Rh(C2O4)Cl(py)3]orthorhombicP212121a=9.9999 b=12.0930 c=14.9368 Z=41806.21.705yellow [27]
CHLOROPENTAAMMINECHROMIUM(III) BIS(OXALATO)PALLADATE[Cr(NH3)5Cl][Pd(C2O4)2]triclinica = 3.225 b = 10.290 c = 11.390 α = 116.5° β = 97.9° γ = 91.2°334.5 [28]
C(NH2)3Cd(C2O4)Cl(H2O)·H2OtriclinicP1a=6.8136 b=7.4890 c=10.0515 α=84.082° β=77.806° γ=88.813°band gap 3.76 eV [29]
SnC2O4Cl2 [30]
SnC2O4Cl2 . CuBr2 1/4EtOHgreen [30]
SnC2O4Cl2 . CuCl2 . H2Ogreen [30]
SnC2O4Cl2 . CoBr2 1/8EtOHrose colour [30]
(Et4N)2C2O4 . SnCl2F2 . 2H2O:white [30]
(Me4N)2Sn(C2O4)Cl2white [30]
(Et4N)2Sn(C2O4)Cl2 .(Et4N)2C2O4(SnCl4)2 . EtOHwhite [30]
Sn(C2O4)2 . 2[SnCl4 . (Pyridine)2]white [30]
(Et4N)2SnCl6 . (Et4N)2C2O4 . 2SnC2O4(OH)2white [30]
(NH4)2Sb(C2O4)Cl3orthorhombicP212121a=8.6961 b=8.7844 c=13.5956 Z=41038.572.253 [31]
K2Sb(C2O4)Cl3orthorhombicP212121a=8.3966 b=8.6023 c=13,6342 Z=4984.802.660 [31]
Rb2Sb(C2O4)Cl3orthorhombicP212121a=8.6769 b=8.8485 c=13.8014 Z=41059.643.053birefringence 0.22@546 nm;NLO 2.1 × KH2PO4 [31]
Ba2Mn2Cl2(C2O4)3·4H2OmonoclinicC2/ca=22.916 b=8.248 c=9.904 β=99.53° [32]
Ba2Fe2Cl2(C2O4)3·4H2OmonoclinicC2/ca=22.798 b=8.297 c=9.849 β=99.90° [32]
Ba2Co2Cl2(C2O4)3·4H2OmonoclinicC2/ca=22.675 b=8.230 c=9.757 β=100.00°purple [33] [32]
BaCd(C2O4)1.5Cl(H2O)2monoclinicC2/ca=23.101 b=8.253 c=10.040 β 99.14°band gap 4.53 eV [29]
La(C2O4)ClmonoclinicP21/na=8.489 b=16.19 c=5.880 β=104.14° [34] [35]
La(C2O4)Cl·3H2O [36]
Ce(C2O4)Cl [1]
Ce(C2O4)Cl·3H2O [36]
Pr(C2O4)Cl·3H2Ostable to 163°C [36] [1]
Nd(C2O4)Cl·3H2Ostable to 167°C; dec 510° to NdOCl [36] [1] [37]
Sm(C2O4)Cl·3H2Ostable to 174°C; dec at 347° to EuC2O4 [36] [1]
Eu(C2O4)Cl·3H2Ostable to 178°C [36] [1]
Gd(C2O4)Cl·3H2O [36] [38]
(Et4N)2Sn(C2O4)Cl2 . (Et4N)2C2O4(SnCl4)2 . EtOH [30]
[(Me4N)2C2O4SnCl4]2 . [(Me4N)2Sn(C2O4)2Cl2]2 . Sn(WO4)2 [30]
[Pt(HC2O4)Cl3]2− [39]
[Pt(HC2O4)(C2O4)Cl]2− [39]
K2[Pt(C2O4)Cl2]·H2OtriclinicP1a=7.136 b=7.308 c=10.130 α=86.75° β=74.58° γ=54.28° Z=2457.73.27 [40] [39]
[Pt(NH3)5Cl][Cr(C2O4)3] · 4H2OorthorhombicPccna=38.901 b=13.7267 c=14.9141 [41]
[Pt(NH3)5Cl][Fe(C2O4)3] · 4H2OorthorhombicPccna=39.0123 b=13.7232 c=14.8990 [41]
[Pt(NH3)5Cl][Co(C2O4)3] · 2H2OmonoclinicP21a=8.5158 b=12.6409 c=8.5726 β=105.000° [41]
lead chloride oxalatePb2Cl2(C2O4)monoclinicC2/ma=5.9411 b=5.8714 c=9.4212 β=95.232° Z=2327.265.82dec 350°C to Pb, Pb5O2Cl6 and Pb3O2Cl2 [42]
Th4Cl4(C2O4)6•20H2O
Plutonium(III) oxalato chloride?Pu(C2O4)Cl·3H2Oblue; biaxial (−) [43]
Am(C2O4)Cl·3H2OmonoclinicP21/na=5.852 b=15.823 c=8.351 β=104.243° [44]

References

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  2. ↑ Lugwisha, E. H. J.; Mulokozi, A. M.; Masabo, M. K. J. (November 1991). "Activation energy of thermal decomposition of LaC2O4Br" . Journal of Thermal Analysis. 37 (11–12): 2567–2572. doi:10.1007/BF01912801. ISSN   0368-4466. S2CID   95356620.
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  7. ↑ Piro, Oscar E.; Echeverría, Gustavo A.; González-Baró, Ana C.; Baran, Enrique J. (February 2018). "Crystal structure and spectroscopic behavior of synthetic novgorodovaite Ca2(C2O4)Cl2·2H2O and its twinned triclinic heptahydrate analog". Physics and Chemistry of Minerals. 45 (2): 185–195. doi:10.1007/s00269-017-0907-0. hdl: 11336/87551 . ISSN   0342-1791. S2CID   103745968.
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  9. ↑ Yoshitake, Masashi; Kubo, Kazuya; Endo, Toru; Noro, Shin-ichiro; Akutagawa, Tomoyuki; Nakamura, Takayoshi (2016-03-15). "Structural Design of Coordination Polymers Based on Manganese and Chromium Ions Bridged by Oxalate Ligands". Bulletin of the Chemical Society of Japan. 89 (3): 354–360. doi:10.1246/bcsj.20150373. ISSN   0009-2673.
  10. 1 2 3 4 Mastropietro, Teresa F.; Marino, Nadia; Munno, Giovanni De; Lloret, Francesc; Julve, Miguel; Pardo, Emilio; Armentano, Donatella (2016-11-07). "Selective Guest Inclusion in Oxalate-Based Iron(III) Magnetic Coordination Polymers" . Inorganic Chemistry. 55 (21): 11160–11169. doi:10.1021/acs.inorgchem.6b01769. ISSN   0020-1669. PMID   27749048.
  11. ↑ Zhang, Bin; Zhang, Yan; Kurmoo, Mohamedally (May 2007). "Preparation, crystal structure and magnetic property of a binuclear oxalate-bridged iron(III) compound: Fe2(C2O4)Cl4(DMF)4 (DMF=dimethylformamide)" . Inorganica Chimica Acta. 360 (7): 2513–2517. doi:10.1016/j.ica.2006.10.028.
  12. ↑ Cot, Sergi; Leu, Meike K.; Kalamiotis, Alexis; Dimitrakis, Georgios; Sans, Victor; de Pedro, Imanol; Cano, Israel (July 2019). "An Oxalate-Bridged Binuclear Iron(III) Ionic Liquid for the Highly Efficient Glycolysis of Polyethylene Terephthalate under Microwave Irradiation". ChemPlusChem. 84 (7): 786–793. doi:10.1002/cplu.201900075. hdl: 10234/185443 . ISSN   2192-6506. PMID   31943995. S2CID   196896383.
  13. ↑ Wang, Lei; Wang, Wenqiang; Guo, Dong; Zhang, Ao; Song, Yaoguang; Zhang, Yiheng; Huang, Keke (2014). "Design and syntheses of hybrid supramolecular architectures: based on [Fe(C 2 O 4 ) 3 ] 3− metallotectons and diverse organic cations" . CrystEngComm. 16 (24): 5437–5449. doi:10.1039/C4CE00357H. ISSN   1466-8033.
  14. ↑ Wang, Lei; Wang, Wenqiang; Guo, Dong; Zhang, Ao; Song, Yaoguang; Zhang, Yiheng; Huang, Keke (2014). "Design and syntheses of hybrid supramolecular architectures: based on [Fe(C 2 O 4 ) 3 ] 3− metallotectons and diverse organic cations" . CrystEngComm. 16 (24): 5437–5449. doi:10.1039/C4CE00357H. ISSN   1466-8033.
  15. ↑ Burazer, Sanja; Molčanov, Krešimir; Šantić, Ana; Klaser, Teodoro; Wenger, Emmanuel; Pajić, Damir; Jagličić, Zvonko; Popović, Jasminka; Jurić, Marijana (2021-09-24). "Humidity-Sensing Properties of an 1D Antiferromagnetic Oxalate-Bridged Coordination Polymer of Iron(III) and Its Temperature-Induced Structural Flexibility". Materials. 14 (19): 5543. Bibcode:2021Mate...14.5543B. doi: 10.3390/ma14195543 . ISSN   1996-1944. PMC   8509436 . PMID   34639934.
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  17. ↑ "Oxalate-Bridged Binuclear Iron (III) Complexes of 3, 5-Dimethylpyrazole Ligands: Synthesis, Structure, Spectral and Electrochemical Properties". International Journal of Chemical Engineering. 31 (2): 1179.
  18. ↑ Zhang, Bin; Wang, Zheming; Zhang, Yan; Takahashi, Kazuyuki; Okano, Yoshinori; Cui, Hengbo; Kobayashi, Hayao; Inoue, Katsuya; Kurmoo, Mohamedally; Pratt, Francis L.; Zhu, Daoben (2006-04-17). "Hybrid Organic−Inorganic Conductor with a Magnetic Chain Anion: κ-BETS 2 [Fe III (C 2 O 4 )Cl 2 ][BETS = Bis(ethylenedithio)tetraselenafulvalene]" . Inorganic Chemistry. 45 (8): 3275–3280. doi:10.1021/ic051870q. ISSN   0020-1669. PMID   16602784.
  19. ↑ Zhang, B.; Zhang, Y.; Wang, Z.; Yang, D.; Gao, Z.; Wang, D.; Guo, Y.; Zhu, D.; Mori, T. (2016). "[BEDT-TTF][Fe(C 2 O 4 )Cl 2 ]: an organic–inorganic hybrid semiconductive antiferromagnet" . Dalton Transactions. 45 (42): 16561–16565. doi:10.1039/C6DT01845A. ISSN   1477-9226. PMID   27344978.
  20. ↑ Zhang, Bin; Zhang, Yan; Gao, Zengqiang; Chang, Guangcai; Su, Shaokui; Wang, Dongwei; Guo, Yanjun; Zhu, Daoben (August 2014). "Synthesis, Crystal Structure, and Characterization of the Charge-Transfer Salt (BEDT-TTF)[Fe(C 2 O 4 )Cl 2 ](CH 2 Cl 2 ), {BEDT‐TTF = Bis(ethylenedithio)tetrathiafulvalene}" . European Journal of Inorganic Chemistry. 2014 (24): 4028–4032. doi:10.1002/ejic.201402112. ISSN   1434-1948.
  21. ↑ Jone Kirubavathy, S.; Velmurugan, R.; Parameswari, K.; Chitra, S. (November 2019). "Synthesis, characterization, single crystal XRD, in vitro antimicrobial and cytotoxicity study of tris(ethylenediamine)cobalt(III)chloride oxalate trihydrate". Arabian Journal of Chemistry. 12 (7): 1581–1586. doi: 10.1016/j.arabjc.2014.10.013 .
  22. ↑ Youngme, Sujittra; Cheansirisomboon, Achareeya; Danvirutai, Chanaiporn; Chaichit, Narongsak; Pakawatchai, Chaveng; van Albada, Gerard A.; Reedijk, Jan (September 2006). "Two new oxalato-bridged dinuclear copper(II) complexes with di-2-pyridylamine: crystal structures, spectroscopic and magnetic properties" . Inorganic Chemistry Communications. 9 (9): 973–977. doi:10.1016/j.inoche.2006.05.022.
  23. ↑ Bahemmat, Samira; Neumüller, Bernhard; Ghassemzadeh, Mitra (August 2015). "One-Pot Synthesis of an Oxalato-Bridged Cu II Coordination Polymer Containing an In Situ Produced Pyrazole Moiety: A Precursor for the Preparation of CuO Nanostructures" . European Journal of Inorganic Chemistry. 2015 (24): 4116–4124. doi:10.1002/ejic.201500255. ISSN   1434-1948.
  24. 1 2 3 4 5 6 7 8 9 Jurić, Marijana; Perić, Berislav; Brničević, Nevenka; Planinić, Pavica; Pajić, Damir; Zadro, Krešo; Giester, Gerald; Kaitner, Branko (2008). "Supramolecular motifs and solvatomorphism within the compounds [M(bpy) 3 ] 2 [NbO(C 2 O 4 ) 3 ]Cl·nH 2 O (M = Fe 2+ , Co 2+ , Ni 2+ , Cu 2+ and Zn 2+ ; n = 11, 12). Syntheses, structures and magnetic properties" . Dalton Trans. (6): 742–754. doi:10.1039/B707937K. ISSN   1477-9226. PMID   18239829.
  25. ↑ Demadis, Konstantinos D.; Chen, Sue-Jane; Coucouvanis, Dimitri (November 1994). "The synthesis, and properties of Fe/Mo/S clusters with MoFe3S4 cubane subunits, Mo bound bidentate oxalate ligands and terminal or bridging cyanide ligands. Structural characterization of (Et4N)3[(C2O4)(CN)MoFe3S4Cl3] and (Et4N)5{[C2O4)MoFe3S4Cl2]2(μ-CN)(μ-S)}". Polyhedron. 13 (22): 3147–3151. doi:10.1016/S0277-5387(00)83684-0. hdl: 2027.42/31244 .
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  27. ↑ Vasilchenko, Danila; Tkachev, Sergey; Baidina, Iraida; Korolkov, Ilya; Berdyugin, Semen; Kozlova, Ekaterina; Kozlov, Denis (2018). "Preparation of a rhodium( iii ) cis -diaquacomplex by protic acid induced oxalate-release from mer -[Rh(C 2 O 4 )Cl(py) 3 ]" . New Journal of Chemistry. 42 (24): 19637–19643. doi:10.1039/C8NJ04264K. ISSN   1144-0546.
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