Salicylaldoxime

Last updated
Salicylaldoxime
Salicylaldoxime.png
Names
IUPAC name
Salicylaldehyde oxime
Other names
Saldox; 2-[(E)-(hydroxyimino)methyl]phenol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.140 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C7H7NO2/c9-7-4-2-1-3-6(7)5-8-10/h1-5,9-10H/b8-5- Yes check.svgY
    Key: ORIHZIZPTZTNCU-YVMONPNESA-N Yes check.svgY
  • InChI=1/C7H7NO2/c9-7-4-2-1-3-6(7)5-8-10/h1-5,9-10H/b8-5-
    Key: ORIHZIZPTZTNCU-YVMONPNEBT
  • Oc1ccccc1/C=N\O
Properties
C7H7NO2
Molar mass 137.138 g·mol−1
Appearancewhite to off-white crystals
Melting point 59 to 61 °C (138 to 142 °F; 332 to 334 K)
25 g L−1
Hazards
NFPA 704 (fire diamond)
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Salicylaldoxime is an organic compound described by the formula C6H4CH=NOH-2-OH. It is the oxime of salicylaldehyde. This crystalline, colorless solid is a chelator and sometimes used in the analysis of samples containing transition metal ions, with which it often forms brightly coloured coordination complexes. [1]

Contents

Reactions

Salicylaldoxime is the conjugate acid of a bidentate ligand:

2 C6H4CH=NOH-2-OH + Cu2+ → Cu(C6H4CH=NOH-2-O)2 + 2 H+

In highly acidic media, the ligand protonates, and the metal aquo complex and aldoxime are liberated. In this way the ligand is used as a recyclable extractant. It typically forms charge-neutral complexes with divalent metal ions.

Analytical chemistry

Structure of the copper(II) complex of the conjugate base of salicylaldoxime. The hydroxyl groups form hydrogen bonds to the phenolate oxygens. Cu(Salox)2.png
Structure of the copper(II) complex of the conjugate base of salicylaldoxime. The hydroxyl groups form hydrogen bonds to the phenolate oxygens.

In the era when metals were analysed by spectrophotometry, many chelating ligands were developed that selectively formed brightly coloured complexes with particular metal ions. This methodology has been eclipsed with the introduction of inductively coupled plasma methodology. Salicylaldoxime can be used to selectively precipitate metal ions for gravimetric determination. It forms a greenish-yellow precipitate with copper at a pH of 2.6 in the presence of acetic acid. Under these conditions, this is the only metal that precipitates; at pH 3.3, nickel also precipitates. Iron (III) will interfere. [2] It has been used as an ionophore in ion selective electrodes, with good response to Pb2+ and Ni2+. [3]

Extraction of metals

Saloximes are used in the extraction and separation of metals from their ores. In one application of hydrometallurgy, Cu2+ is extracted into organic solvents as its saloxime complex. [4]

Related Research Articles

<span class="mw-page-title-main">Coordination complex</span> Molecule or ion containing ligands datively bonded to a central metallic atom

A coordination complex consists of a central atom or ion, which is usually metallic and is called the coordination centre, and a surrounding array of bound molecules or ions, that are in turn known as ligands or complexing agents. Many metal-containing compounds, especially those that include transition metals, are coordination complexes.

<span class="mw-page-title-main">Oxime</span> Organic compounds of the form >C=N–OH

In organic chemistry, an oxime is a organic compound belonging to the imines, with the general formula RR’C=N−OH, where R is an organic side-chain and R’ may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides with general structure R1C(=NOH)NR2R3.

<span class="mw-page-title-main">Fehling's solution</span> Chemical test for the reducibility of a sugar

In organic chemistry, Fehling's solution is a chemical reagent used to differentiate between water-soluble carbohydrate and ketone functional groups, and as a test for reducing sugars and non-reducing sugars, supplementary to the Tollens' reagent test. The test was developed by German chemist Hermann von Fehling in 1849.

<span class="mw-page-title-main">Copper(II) nitrate</span> Chemical compound

Copper(II) nitrate describes any member of the family of inorganic compounds with the formula Cu(NO3)2(H2O)x. The hydrates are blue solids. Anhydrous copper nitrate forms blue-green crystals and sublimes in a vacuum at 150-200 °C. Common hydrates are the hemipentahydrate and trihydrate.

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

Copper(II) chloride is the chemical compound with the chemical formula CuCl2. The anhydrous form is yellowish brown but slowly absorbs moisture to form a blue-green dihydrate.

<span class="mw-page-title-main">1,10-Phenanthroline</span> Heterocyclic organic compound

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<span class="mw-page-title-main">Metal ammine complex</span>

In coordination chemistry, metal ammine complexes are metal complexes containing at least one ammonia ligand. "Ammine" is spelled this way due to historical reasons; in contrast, alkyl or aryl bearing ligands are spelt with a single "m". Almost all metal ions bind ammonia as a ligand, but the most prevalent examples of ammine complexes are for Cr(III), Co(III), Ni(II), Cu(II) as well as several platinum group metals.

Liquid–liquid extraction (LLE), also known as solvent extraction and partitioning, is a method to separate compounds or metal complexes, based on their relative solubilities in two different immiscible liquids, usually water (polar) and an organic solvent (non-polar). There is a net transfer of one or more species from one liquid into another liquid phase, generally from aqueous to organic. The transfer is driven by chemical potential, i.e. once the transfer is complete, the overall system of chemical components that make up the solutes and the solvents are in a more stable configuration. The solvent that is enriched in solute(s) is called extract. The feed solution that is depleted in solute(s) is called the raffinate. LLE is a basic technique in chemical laboratories, where it is performed using a variety of apparatus, from separatory funnels to countercurrent distribution equipment called as mixer settlers. This type of process is commonly performed after a chemical reaction as part of the work-up, often including an acidic work-up.

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

Dimethylglyoxime is a chemical compound described by the formula CH3C(NOH)C(NOH)CH3. Its abbreviation is dmgH2 for neutral form, and dmgH for anionic form, where H stands for hydrogen. This colourless solid is the dioxime derivative of the diketone butane-2,3-dione (also known as diacetyl). DmgH2 is used in the analysis of palladium or nickel. Its coordination complexes are of theoretical interest as models for enzymes and as catalysts. Many related ligands can be prepared from other diketones, e.g. benzil.

<span class="mw-page-title-main">Uranyl</span> Oxycation of uranium

The uranyl ion is an oxycation of uranium in the oxidation state +6, with the chemical formula UO2+
2
. It has a linear structure with short U–O bonds, indicative of the presence of multiple bonds between uranium and oxygen. Four or more ligands may be bound to the uranyl ion in an equatorial plane around the uranium atom. The uranyl ion forms many complexes, particularly with ligands that have oxygen donor atoms. Complexes of the uranyl ion are important in the extraction of uranium from its ores and in nuclear fuel reprocessing.

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

Chloroplatinic acid (also known as hexachloroplatinic acid) is an inorganic compound with the formula [H3O]2[PtCl6](H2O)x (0 ≤ x ≤ 6). A red solid, it is an important commercial source of platinum, usually as an aqueous solution. Although often written in shorthand as H2PtCl6, it is the hydronium (H3O+) salt of the hexachloroplatinate anion (PtCl2−
6
). Hexachloroplatinic acid is highly hygroscopic.

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

Nitrilotriacetic acid (NTA) is the aminopolycarboxylic acid with the formula N(CH2CO2H)3. It is a colourless solid that is used as a chelating agent, which forms coordination compounds with metal ions (chelates) such as Ca2+, Co2+, Cu2+, and Fe3+.

<span class="mw-page-title-main">Coordination polymer</span> Polymer consisting of repeating units of a coordination complex

A coordination polymer is an inorganic or organometallic polymer structure containing metal cation centers linked by ligands. More formally a coordination polymer is a coordination compound with repeating coordination entities extending in 1, 2, or 3 dimensions.

<span class="mw-page-title-main">Hydroxamic acid</span> Organic compounds of the form –C(=O)N(OH)–

In organic chemistry, hydroxamic acids are a class of organic compounds bearing the functional group R−C(=O)−N(OH)−R', with R and R' as organic residues. They are amides wherein the nitrogen center has a hydroxyl substituent. They are often used as metal chelators.

<span class="mw-page-title-main">Hexafluorophosphate</span> Anion with the chemical formula PF6–

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<span class="mw-page-title-main">Tetrakis(acetonitrile)copper(I) hexafluorophosphate</span> Chemical compound

Tetrakis(acetonitrile)copper(I) hexafluorophosphate is a salt with the formula [Cu(CH3CN)4]PF6. It is a colourless solid that is used in the synthesis of other copper complexes. The cation [Cu(CH3CN)4]+ is a well-known example of a transition metal nitrile complex.

Binding selectivity is defined with respect to the binding of ligands to a substrate forming a complex. Binding selectivity describes how a ligand may bind more preferentially to one receptor than another. A selectivity coefficient is the equilibrium constant for the reaction of displacement by one ligand of another ligand in a complex with the substrate. Binding selectivity is of major importance in biochemistry and in chemical separation processes.

<span class="mw-page-title-main">Transition metal imidazole complex</span>

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References

  1. Smith, Andrew G.; Tasker, Peter A.; White, David J. "The structures of phenolic oximes and their complexes" Coordination Chemistry Reviews 2003, volume24, pp. 61-85. doi : 10.1016/S0010-8545(02)00310-7
  2. SH Simonsen; HM Burnett (1955). "Spectrophotometric Determination Of Copper With Salicylaldoxime - Application To Analysis Of Aluminum Alloys". Analytical Chemistry. 27 (8): 1336–1339. doi:10.1021/ac60104a039.
  3. EK Quagraine; VPY Gadzekpo (December 1992). "Studies Of Spectrophotometric Reagents In Some Transition-Metal And Lead Ion-Selective Electrodes". Analyst. 117 (12): 1899–1903. Bibcode:1992Ana...117.1899Q. doi:10.1039/an9921701899.
  4. Tasker, Peter A.; Tong, Christine C.; Westra, Arjan N. (2007). "Co-extraction of Cations and Anions in Base Metal Recovery". Coordination Chemistry Reviews. 251 (13–14): 1868–1877. doi:10.1016/j.ccr.2007.03.014.