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Chemical tagging of chlorinated phenols for their facile detection and analysis by NMR spectroscopy

Journal Article · · Analytical and Bioanalytical Chemistry
 [1];  [1]
  1. Lawrence Livermore National Laboratory (LLNL), Livermore, CA (United States)
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A derivatization method that employs diethyl (bromodifluoromethyl) phosphonate (DBDFP) to efficiently tag the endocrine disruptor pentachlorophenol (PCP) and other chlorinated phenols (CPs) along with their reliable detection and analysis by NMR is presented. The method accomplishes the efficient alkylation of the hydroxyl group in CPs with the difluoromethyl (CF2H) moiety in extremely rapid fashion (5 min), at room temperature and in an environmentally benign manner. The approach proved successful in difluoromethylating a panel of 18 chlorinated phenols, yielding derivatives that displayed unique 1H, 19F NMR spectra allowing for the clear discrimination between isomerically related CPs. Due to its biphasic nature, the derivatization can be applied to both aqueous and organic mixtures where the analysis of CPs is required. Furthermore, the methodology demonstrates that PCP along with other CPs can be selectively derivatized in the presence of other various aliphatic alcohols, underscoring the superiority of the approach over other general derivatization methods that indiscriminately modify all analytes in a given sample. The present work demonstrates the first application of NMR on the qualitative analysis of these highly toxic and environmentally persistent species.

Research Organization:
Lawrence Livermore National Laboratory (LLNL), Livermore, CA (United States)
Sponsoring Organization:
USDOE
DOE Contract Number:
AC52-07NA27344
OSTI ID:
1182243
Report Number(s):
LLNL--JRNL-666745
Journal Information:
Analytical and Bioanalytical Chemistry, Journal Name: Analytical and Bioanalytical Chemistry Journal Issue: 13 Vol. 407; ISSN 1618-2642
Publisher:
Springer
Country of Publication:
United States
Language:
English

References (11)

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Derivatisation in gas chromatographic determination of acidic herbicides in aqueous environmental samples journal October 2003
Diethyl bromodifluoromethylphosphonate: a highly efficient and environmentally benign difluorocarbene precursor journal July 2009
Endocrine Disrupting Effects of Herbicides and Pentachlorophenol: In Vitro and in Vivo Evidence journal March 2009
A simple convenient method for preparation of difluoromethyl ethers using fluorosulfonyldifluoroacetic acid as a difluorocarbene precursor journal September 1989

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
71 CLASSICAL AND QUANTUM MECHANICS
GENERAL PHYSICS
NMR
difluoromethylation
endocrine disruptor
pentachlorophenol