Salicylaldoxime

From Wikipedia, the free encyclopedia

Salicylaldoxime
IUPAC name Salicylaldehyde oxime
Other names Saldox
Identifiers
CAS number [94-67-7]
PubChem 5359280
SMILES C1=CC(=CNO)C(=O)C=C1
Properties
Molecular formula C7H7NO2
Molar mass 137.14 g mol-1
Appearance white to off-white crystals
Melting point

59-61 °C
Solubility in water 25 g L-1
Hazards
NFPA 704
1
2
0
 
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Salicylaldoxime is a chemical compound described by the formula C6H4CH=NOH-2-OH. It is the oxime of salicylaldehyde. This crystalline 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]

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]

Adsorbed or chemically bonded to a solid support such as silica gel, it can be used to preconcentrate or extract metals from a dilute solution such as seawater.[3] It has been used as an ionophore in ion selective electrodes, with good response to Pb2+ and Ni2+.[4]

Salicylaldoxime has also been used to probe ion channels in muscle tissue[5] and as a probe in photosystem I.[6]

[edit] External links

[edit] References

  1. ^ P Sedwick; D Shinn, H Zeitlin (1984). ""The Separation Of Metals From Treated Deep-Sea Ferromanganese Nodules By Adsorptive Bubble Techniques Using Salicylaldoxime And Sodium Diethyldithiocarbamate As Organic Precipitating Reagents"". Separation Science and Technology 19 (2-3): 183-190. doi:10.1080/01496398408060654. 
  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. ^ AR Sarkar; PK Datta, M Sarkar (November 1996). ""Sorption Recovery of Metal Ions Using Silica Gel Modified with Salicylaldoxime"". Talanta 43 (11): 1857-1862. doi:10.1016/0039-9140(96)01953-4. 
  4. ^ EK Quagraine; VPY Gadzekpo (December 1992). ""Studies Of Spectrophotometric Reagents In Some Transition-Metal And Lead Ion-Selective Electrodes"". Analyst 117 (12): 1899-1903. doi:10.1039/an9921701899. 
  5. ^ H Chunlei; LC Sellin (December 1995). ""Multiple Effects Of Salicylaldoxime On Rat Cardiac Action-Potentials"". Pharmacology & Toxicology 77 (6): 386-390. PMID 8835364. 
  6. ^ S Katoh; A San Pietro (1966). ""Inhibitory Effect Of Salicylaldoxime On Chloroplast Photooxidation-Reduction Reactions"". Biochemical and Biophysical Research Communications 24 (6): 903. doi:10.1016/0006-291X(66)90335-4. PMID 5970525.