Salicylaldoxime

Chembox new
ImageFile = Salicylaldoxime.png ImageSize = 200px
IUPACName = Salicylaldehyde oxime
OtherNames = Saldox
Section1 = Chembox Identifiers
CASNo = 94-67-7
PubChem = 5359280
SMILES = C1=CC(=CNO)C(=O)C=C1
Section2 = Chembox Properties
Formula = |C=7 |H=7 |N=1 |O=2
MolarMass = 137.13598
Appearance = white to off-white crystals
Density =
MeltingPt = 59-61 °C
BoilingPt =
Solubility = 25 g L^-1
Section3 = Chembox Hazards
MainHazards =
NFPA-H = 2
NFPA-F = 1
NFPA-R = 0
FlashPt =
Autoignition =

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. [cite journal
author = P Sedwick
coauthors = D Shinn, H Zeitlin
year = 1984
title = "The Separation Of Metals From Treated Deep-Sea Ferromanganese Nodules By Adsorptive Bubble Techniques Using Salicylaldoxime And Sodium Diethyldithiocarbamate As Organic Precipitating Reagents"
journal = Separation Science and Technology
volume = 19
issue = 2-3
pages = 183–190
doi = 10.1080/01496398408060654]

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. [cite journal
author = SH Simonsen
coauthors = HM Burnett
year = 1955
title = "Spectrophotometric Determination Of Copper With Salicylaldoxime - Application To Analysis Of Aluminum Alloys"
journal = Analytical Chemistry
volume = 27
issue = 8
pages = 1336–1339
doi = 10.1021/ac60104a039]

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. [cite journal
author = AR Sarkar
coauthors = PK Datta, M Sarkar
year = 1996
month = November
title = "Sorption Recovery of Metal Ions Using Silica Gel Modified with Salicylaldoxime"
journal = Talanta
volume = 43
issue = 11
pages = 1857–1862
doi = 10.1016/0039-9140(96)01953-4] It has been used as an ionophore in ion selective electrodes, with good response to Pb²⁺ and Ni²⁺. [cite journal
author = EK Quagraine
coauthors = VPY Gadzekpo
year = 1992
month = December
title = "Studies Of Spectrophotometric Reagents In Some Transition-Metal And Lead Ion-Selective Electrodes"
journal = Analyst
volume = 117
issue = 12
pages = 1899–1903
doi = 10.1039/an9921701899]

Salicylaldoxime has also been used to probe ion channels in muscle tissue [cite journal
author = H Chunlei
coauthors = LC Sellin
year = 1995
month = December
title = "Multiple Effects Of Salicylaldoxime On Rat Cardiac Action-Potentials"
journal = Pharmacology & Toxicology
volume = 77
issue = 6
pages = 386–390
pmid = 8835364] and as a probe in photosystem I. [cite journal
author = S Katoh
coauthors = A San Pietro
year = 1966
title = "Inhibitory Effect Of Salicylaldoxime On Chloroplast Photooxidation-Reduction Reactions"
journal = Biochemical and Biophysical Research Communications
volume = 24
issue = 6
pages = 903
pmid = 5970525
doi = 10.1016/0006-291X(66)90335-4]

External links

* [http://webbook.nist.gov/cgi/cbook.cgi?ID=C94677 Chemical data at NIST Chemistry WebBook]

References