Sodium hydrogenoxalate

Last updated
Sodium hydrogenoxalate
Sodium hydrogenoxalate.svg
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]
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.356 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 214-691-3
PubChem CID
UNII
  • 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
  • [Na+].[O-]C(=O)C(=O)O
Properties
C2HNaO4
Molar mass 112.0167 [3]
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H312
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)
Oxalate (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).

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

Contents

Properties

Hydrates

The compound is commonly encountered as the anhydrous form or as the monohydrate NaHC
2
O
4
·H
2
O
. 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 P1). 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
2
O
4
Na
2
C
2
O
4
+ H
2
C
2
O
4
Na
2
C
2
O
4
Na
2
CO
3
+ 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]

Related Research Articles

<span class="mw-page-title-main">Carbonate</span> Salt of carbonic acid

A carbonate is a salt of carbonic acid (H2CO3), characterized by the presence of the carbonate ion, a polyatomic ion with the formula CO2−3. The word carbonate may also refer to a carbonate ester, an organic compound containing the carbonate group C(=O)(O–)2.

<span class="mw-page-title-main">Ionic bonding</span> Chemical bonding involving attraction between ions

Ionic bonding is a type of chemical bonding that involves the electrostatic attraction between oppositely charged ions, or between two atoms with sharply different electronegativities, and is the primary interaction occurring in ionic compounds. It is one of the main types of bonding along with covalent bonding and metallic bonding. Ions are atoms with an electrostatic charge. Atoms that gain electrons make negatively charged ions. Atoms that lose electrons make positively charged ions. This transfer of electrons is known as electrovalence in contrast to covalence. In the simplest case, the cation is a metal atom and the anion is a nonmetal atom, but these ions can be of a more complex nature, e.g. molecular ions like NH+
4
or SO2−
4
. In simpler words, an ionic bond results from the transfer of electrons from a metal to a non-metal in order to obtain a full valence shell for both atoms.

Carbon compounds are defined as chemical substances containing carbon. More compounds of carbon exist than any other chemical element except for hydrogen. Organic carbon compounds are far more numerous than inorganic carbon compounds. In general bonds of carbon with other elements are covalent bonds. Carbon is tetravalent but carbon free radicals and carbenes occur as short-lived intermediates. Ions of carbon are carbocations and carbanions are also short-lived. An important carbon property is catenation as the ability to form long carbon chains and rings.

In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively charged sodium ions and negatively charged chloride ions.

<span class="mw-page-title-main">Sodium hydroxide</span> Chemical compound with formula NaOH

Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations Na+ and hydroxide anions OH.

The chloride ion is the anion Cl. It is formed when the element chlorine gains an electron or when a compound such as hydrogen chloride is dissolved in water or other polar solvents. Chloride salts such as sodium chloride are often very soluble in water. It is an essential electrolyte located in all body fluids responsible for maintaining acid/base balance, transmitting nerve impulses and regulating liquid flow in and out of cells. Less frequently, the word chloride may also form part of the "common" name of chemical compounds in which one or more chlorine atoms are covalently bonded. For example, methyl chloride, with the standard name chloromethane is an organic compound with a covalent C−Cl bond in which the chlorine is not an anion.

<span class="mw-page-title-main">Sulfate</span> Oxyanion with a central atom of sulfur surrounded by 4 oxygen atoms

The sulfate or sulphate ion is a polyatomic anion with the empirical formula SO2−4. Salts, acid derivatives, and peroxides of sulfate are widely used in industry. Sulfates occur widely in everyday life. Sulfates are salts of sulfuric acid and many are prepared from that acid.

<span class="mw-page-title-main">Calcium oxalate</span> Calcium compound

Calcium oxalate (in archaic terminology, oxalate of lime) is a calcium salt of oxalic acid with the chemical formula CaC2O4. It forms hydrates CaC2O4·nH2O, where n varies from 1 to 3. Anhydrous and all hydrated forms are colorless or white. The monohydrate CaC2O4·H2O occurs naturally as the mineral whewellite, forming envelope-shaped crystals, known in plants as raphides. The two rarer hydrates are dihydrate CaC2O4·2H2O, which occurs naturally as the mineral weddellite, and trihydrate CaC2O4·3H2O, which occurs naturally as the mineral caoxite, are also recognized. Some foods have high quantities of calcium oxalates and can produce sores and numbing on ingestion and may even be fatal. Tribes with diets that depend highly on fruits and vegetables high in calcium oxalate, such as in Micronesia, reduce the level of it by boiling and cooking them. They are a constituent in 76% of human kidney stones. Calcium oxalate is also found in beerstone, a scale that forms on containers used in breweries.

<span class="mw-page-title-main">Oxalic acid</span> Simplest dicarboxylic acid

Oxalic acid is an organic acid with the systematic name ethanedioic acid and formula HO2C−CO2H. It is the simplest dicarboxylic acid. It is a white crystalline solid that forms a colorless solution in water. Its name comes from the fact that early investigators isolated oxalic acid from flowering plants of the genus Oxalis, commonly known as wood-sorrels. It occurs naturally in many foods. Excessive ingestion of oxalic acid or prolonged skin contact can be dangerous.

<span class="mw-page-title-main">Oxalate</span> Any derivative of oxalic acid; chemical compound containing oxalate moiety

Oxalate (IUPAC: ethanedioate) is an anion with the formula C2O42−. This dianion is colorless. It occurs naturally, including in some foods. It forms a variety of salts, for example sodium oxalate (Na2C2O4), and several esters such as dimethyl oxalate (C2O4(CH3)2). It is a conjugate base of oxalic acid. At neutral pH in aqueous solution, oxalic acid converts completely to oxalate.

<span class="mw-page-title-main">Sodium oxalate</span> Chemical compound

Sodium oxalate, or disodium oxalate, is the sodium salt of oxalic acid with the formula Na2C2O4. It is a white, crystalline, odorless solid, that decomposes above 290 °C.

In chemical nomenclature, the IUPAC nomenclature of inorganic chemistry is a systematic method of naming inorganic chemical compounds, as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in Nomenclature of Inorganic Chemistry. Ideally, every inorganic compound should have a name from which an unambiguous formula can be determined. There is also an IUPAC nomenclature of organic chemistry.

<span class="mw-page-title-main">Acetylenedicarboxylic acid</span> Chemical compound

Acetylenedicarboxylic acid or butynedioic acid is an organic compound (a dicarboxylic acid) with the formula C4H2O4 or HO2CC≡CCO2H. It is a crystalline solid that is soluble in diethyl ether.

<span class="mw-page-title-main">Hydrogenoxalate</span> Ion

Hydrogenoxalate or hydrogen oxalate is an anion with chemical formula HC
2
O
4
or HO
2
C–CO
2
, derived from oxalic acid by the loss of a single proton; or, alternatively, from the oxalate anion C
2
O2−
4
by addition of a proton. The name is also used for any salt containing this anion. Especially in older literature, hydrogenoxalates may also be referred to as bioxalates, acid oxalates, or monobasic oxalates. Hydrogenoxalate is amphoteric, in that it can react both as an acid or a base.

<span class="mw-page-title-main">Potassium hydrogenoxalate</span> Chemical compound, salt of sorrel

Potassium hydrogenoxalate is a salt with formula KHC2O4 or K+·HO2C-CO2. It is one of the most common salts of the hydrogenoxalate anion, and can be obtained by reacting potassium hydroxide with oxalic acid in 1:1 mole ratio.

<span class="mw-page-title-main">Oxocarbon anion</span> Negatively-charged molecule made of carbon and oxygen

In chemistry, an oxocarbon anion is a negative ion consisting solely of carbon and oxygen atoms, and therefore having the general formula C
x
On
y
for some integers x, y, and n.

<span class="mw-page-title-main">Berkelium(III) chloride</span> Chemical compound

Berkelium(III) chloride also known as berkelium trichloride, is a chemical compound with the formula BkCl3. It is a water-soluble green solid with a melting point of 603 °C. This compound forms the hexahydrate, BkCl3·6H2O.

<span class="mw-page-title-main">Niobium oxalate</span> Chemical compound

Niobium(V) oxalate is the hydrogen oxalate salt of niobium(V). The neutral salt has not been prepared.

<span class="mw-page-title-main">Sodium tetrahydroxyborate</span> Chemical compound

Sodium tetrahydroxyborate is a salt (ionic compound) of with chemical formula NaH4BO4 or Na+[B(OH)4]. It is one of several sodium borates. At room temperature it is a colorless transparent crystalline solid.

Alkali citrate is an inhibitor of kidney stones. It is used to increase urine citrate levels - this prevents calcium oxalate stones by binding to calcium and inhibiting its binding to oxalate. It is also used to increase urine pH - this prevents uric acid stones and cystine stones.

References

  1. 1 2 "2T9TH558WS: NaHC2O4". ChemSpider website, accessed on 2018-09-11
  2. 1 2 "Monosodium oxalate". NCBI PubChem website, accessed on 2018-09-11
  3. "Sodium Hydrogen Oxalate NaHC2O4". EndMemo.com website, accessed on 2018-09-11
  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
  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.