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Radioiodination of humic substances via azocoupling with 3-[ I]iodoaniline

Environmental Science and Technology, ISSN: 0013-936X, Vol: 42, Issue: 11, Page: 4083-4087
2008
  • 5
    Citations
  • 0
    Usage
  • 14
    Captures
  • 0
    Mentions
  • 0
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    5
    • Citation Indexes
      5
  • Captures
    14

Article Description

A new method is described for radiolabeling humic substances (HS) with iodine radioisotopes. The method radiolabels the electron-rich aromatic moieties of HS with the 3-[I]iodobenzenediazonium ion via azocoupling. The method uses four steps: (i) 3-aminobenzenetrimethylstannane is synthesized and isolated by using a silica gel column, (ii) 3-[I]iodoaniline is synthesized and isolated by HPLC, with radiochemical yields of up to 60%, (iii) 3-[I]iodobenzenediazonium chloride is synthesized, and the reaction mixture from this step is used in step iv to radioiodinate HS with radiochemical yields of up to 95% (with reference to 3-[I] iodoaniline). The advantage of this method is that it is selective radiolabeling, placing the radiolabel in a specific site (the 3-position of the phenyl ring) within HS molecules, which minimizes unwanted secondary chemical interactions. Investigations of the stability of the radiolabel and the effect of photoreductive dehalogenation showed that there was a negligible release of I. The production of radiolabeled HS using this method allows the sensitive detection of HS in laboratory and field studies. In addition, the method offers the possibility of using different iodine radioisotopes simultaneously in investigations using HS. © 2008 American Chemical Society.

Bibliographic Details

Franke, Karsten; Patt, Jörg T; Kupsch, Hermann; Warwick, Peter

American Chemical Society (ACS)

Chemistry; Environmental Science

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