Journal article
The formation of disulfides by the [Fe(nta)Cl 2] 2− catalyzed air oxidation of thiols and dithiols
Inorganica Chimica Acta, Vol.359(12), pp.3996-4000
2006
DOI: 10.1016/j.ica.2006.03.043
Abstract
The iron(III) dichloronitrilotriacetate ion, [Fe(nta)Cl
2]
2−, catalyzes the air oxidation of thiols and α,ω-dithiols to disulfides and oligomeric disulfides, respectively. Oligomeric products from the oxidation of propane-, butane- and pentanedithiol have been characterized by field desorption mass spectrometry and shown to form monomeric to decameric oligomers. The identity of the oligomer terminal groups is partially dependent on the nature of the catalyst counterion. The [Fe(nta)Cl
2]
2− ion has been characterized by electrospray mass spectrometry.
The complexes (cnt)
2[Fe(nta)Cl
2], where nta
=
nitrilotriacetate and cnt
=
Et
4N
+ or PyH
+, catalyze the air oxidation of thiols to disulfides under ambient conditions. Dithiols are converted to linear and cyclic oligomers that differ in their terminal groups as a function of the counterion, cnt. Cysteine ethyl ester was converted to the corresponding cystine diethylester in high yield.
Details
- Title: Subtitle
- The formation of disulfides by the [Fe(nta)Cl 2] 2− catalyzed air oxidation of thiols and dithiols
- Creators
- Marc A Walters - Department of Chemistry, New York University, New York, NY 10003, USAJacqueline Chaparro - Department of Chemistry, New York University, New York, NY 10003, USATalha Siddiqui - Department of Chemistry, New York University, New York, NY 10003, USAFlorence Williams - Department of Chemistry, New York University, New York, NY 10003, USACaleb Ulku - Department of Chemistry, New York University, New York, NY 10003, USAArnold L Rheingold - Department of Chemistry and Biochemistry, University of California-San Diego, La Jolla, CA 92093, USA
- Resource Type
- Journal article
- Publication Details
- Inorganica Chimica Acta, Vol.359(12), pp.3996-4000
- Publisher
- Elsevier B.V
- DOI
- 10.1016/j.ica.2006.03.043
- ISSN
- 0020-1693
- eISSN
- 1873-3255
- Language
- English
- Date published
- 2006
- Academic Unit
- Chemistry; Iowa Neuroscience Institute
- Record Identifier
- 9984065471802771
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