Sodium hydrogenoxalate

Sodium hydrogenoxalate
Names
	Preferred IUPAC name Sodium carboxyformate
	Other names Ethanedioate, hydrogen sodium salt (1:1:1); Ethanedioic acid, sodium salt (1:1); Monosodium oxalate; Sodium hydrogen ethanedioate (1:1:1); Oxalic acid sodium salt; Oxalic acid, sodium salt; Sodium acid oxalate; Sodium and hydrogen and oxalate; Sodium bioxalate
Identifiers
CAS Number	1186-49-8;
3D model (JSmol)	Interactive image;
ChemSpider	4953678;
ECHA InfoCard	100.013.356
EC Number	214-691-3;
PubChem CID	23684893;
UNII	2T9TH558WS;
CompTox Dashboard (EPA)	DTXSID1047499 ;
	InChI InChI=1S/C2H2O4.Na/c3-1(4)2(5)6;/h(H,3,4)(H,5,6);/q;+1/p-1 Key: UJRAXLUXHBUNDO-UHFFFAOYSA-M;
	SMILES [Na+].[O-]C(=O)C(=O)O;
Properties
Chemical formula	C2HNaO4
Molar mass	112.0167
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312
Precautionary statements	P264, P270, P280, P301+P312, P302+P352, P312, P322, P330, P363, P501
Related compounds
Other anions	Sodium bicarbonate (oxalate replaced with carbonate)
Other cations	Potassium hydrogenoxalate (potassium instead of sodium); Oxalic acid (hydrogen instead of sodium); Sodium oxalate (sodium instead of hydrogen)
Related compounds	Hydrogenoxalate (sodium ion removed); Hydrogenoxalate (sodium and hydrogen ions removed)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Sodium hydrogenoxalate is salt (ionic compound) of formula NaHC
₂O
₄, consisting of sodium cations Na⁺
and hydrogenoxalate anions HC
₂O⁻
₄ or -. The anion can be described as the result of removing one hydrogen ion H⁺
from oxalic acid H
₂C
₂O
₄, or adding one to the oxalate cation C
₂O²⁺
₄.

Properties[]

Hydrates[]

The compound is commonly encountered as the anhydrous form or as the monohydrate NaHC
₂O
₄.H
₂O. Both are colorless crystalline solids at ambient temperature.

The monohydrate can be obtained by evaporating a solution of the compound at room temperature.^[4]

The crystal structure of NaHC2O4·H2O is triclinic normal (pinacoidal, space group $P_{\bar {1}}$ ). The lattice parameters are a = 650.3 pm, b = 667.3 pm, c = 569.8 pm, α = 85.04°, β = 110.00°, γ = 105.02°, and Z = 2. The hydrogen oxalate ions are linked end to end in infinite chains by hydrogen bonds (257.1 pm). The chains are cross linked to form layers by both O–H···O bonds from the water molecules (280.8 pm, 282.6 pm) and by ionic bonds Na+···O. These layers are in turn held together by Na+···O bonds. The oxalate group is non-planar with an angle of twist about the C–C bond of 12.9°.^[5]

Reactions[]

Upon being heated, sodium hydrogenoxalate converts to oxalic acid and sodium oxalate, the latter of which decomposes into sodium carbonate and carbon monoxide.^[6]

2NaHC
₂O
₄ → Na
₂C
₂O
₄ + H
₂C
₂O
₄

Na
₂C
₂O
₄ → Na
₂CO3 + CO

Toxicity[]

The health hazards posed by this compound are largely due to its acidity and to the toxic effects of oxalic acid and other oxalate or hydrogenoxalate salts, which can follow ingestion or absorption through the skin. The toxic effects include necrosis of tissues due to sequestration of calcium ions, and the formation of poorly soluble calcium oxalate stones in the kidneys that can obstruct the kidney tubules.^[2]

References[]

^ ^a ^b "2T9TH558WS: NaHC2O4". ChemSpider website, accessed on 2018-09-11
^ ^a ^b "Monosodium oxalate". NCBI PubChem website, accessed on 2018-09-11
^ "Sodium Hydrogen Oxalate NaHC₂O₄". EndMemo.com website, accessed on 2018-09-11
^ C. Ramki, R. Ezhil Vizhi (2017): "Growth, optical, electrical and mechanical properties of sodium hydrogen oxalate hydrate (NaHC2O4·H2O) single crystal for NLO applications". Materials Chemistry and Physics, volume 197, pages 70-78. doi:10.1016/j.matchemphys.2017.04.066
^ Roland Tellgren and Ivar Olovsson (1971): "Hydrogen Bond Studies. XXXXVI. The Crystal Structures of Normal and Deuterated Sodium Hydrogen Oxalate Monohydrate NaHC2O4·H2O and NaDC2O4·D2O". Journal of Chemical Physics, volume 54, issue 1. doi:10.1063/1.1674582
^ W. Balcerowiak; Cz. Latocha; J. Wasilewski (1980). "Thermoanalytical investigation of mixtures containing oxalic acid, sodium hydrogen oxalate and sodium oxalate". Journal of Thermal Analysis. 18: 57–63. doi:10.1007/BF01909453.

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[chsp2018-1] "2T9TH558WS: NaHC2O4". ChemSpider website, accessed on 2018-09-11

[ncbi2018-2] "Monosodium oxalate". NCBI PubChem website, accessed on 2018-09-11

[endm2018-3] "Sodium Hydrogen Oxalate NaHC₂O₄". EndMemo.com website, accessed on 2018-09-11

[ramk2017-4] C. Ramki, R. Ezhil Vizhi (2017): "Growth, optical, electrical and mechanical properties of sodium hydrogen oxalate hydrate (NaHC2O4·H2O) single crystal for NLO applications". Materials Chemistry and Physics, volume 197, pages 70-78. doi:10.1016/j.matchemphys.2017.04.066

[tell1971-5] Roland Tellgren and Ivar Olovsson (1971): "Hydrogen Bond Studies. XXXXVI. The Crystal Structures of Normal and Deuterated Sodium Hydrogen Oxalate Monohydrate NaHC2O4·H2O and NaDC2O4·D2O". Journal of Chemical Physics, volume 54, issue 1. doi:10.1063/1.1674582

[6] W. Balcerowiak; Cz. Latocha; J. Wasilewski (1980). "Thermoanalytical investigation of mixtures containing oxalic acid, sodium hydrogen oxalate and sodium oxalate". Journal of Thermal Analysis. 18: 57–63. doi:10.1007/BF01909453.

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Names

Preferred IUPAC name Sodium carboxyformate
Other names Ethanedioate, hydrogen sodium salt (1:1:1) Ethanedioic acid, sodium salt (1:1) Monosodium oxalate Sodium hydrogen ethanedioate (1:1:1) Oxalic acid sodium salt Oxalic acid, sodium salt Sodium acid oxalate Sodium and hydrogen and oxalate Sodium bioxalate^[1]
Identifiers^[2]^[1]
CAS Number	1186-49-8
3D model (JSmol)	Interactive image
ChemSpider	4953678
ECHA InfoCard	100.013.356
EC Number	214-691-3
PubChem CID	23684893
UNII	2T9TH558WS
CompTox Dashboard (EPA)	DTXSID1047499
InChI InChI=1S/C2H2O4.Na/c3-1(4)2(5)6;/h(H,3,4)(H,5,6);/q;+1/p-1 Key: UJRAXLUXHBUNDO-UHFFFAOYSA-M
SMILES [Na+].[O-]C(=O)C(=O)O
Properties
Chemical formula	C₂HNaO₄
Molar mass	112.0167^[3]
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312
Precautionary statements	P264, P270, P280, P301+P312, P302+P352, P312, P322, P330, P363, P501
Related compounds
Other anions	Sodium bicarbonate (oxalate replaced with carbonate)
Other cations	Potassium hydrogenoxalate (potassium instead of sodium) Oxalic acid (hydrogen instead of sodium) Sodium oxalate (sodium instead of hydrogen)
Related compounds	Hydrogenoxalate (sodium ion removed) Hydrogenoxalate (sodium and hydrogen ions removed)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references