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Environmental properties of pentafluorosulfanyl compounds: Physical properties and photodegradation
Author(s) -
Jackson Derek A.,
Mabury Scott A.
Publication year - 2009
Publication title -
environmental toxicology and chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.1
H-Index - 171
eISSN - 1552-8618
pISSN - 0730-7268
DOI - 10.1897/09-037.1
Subject(s) - chemistry , photodegradation , environmental chemistry , trifluoromethyl , mass spectrometry , fluoride , organic chemistry , photocatalysis , catalysis , chromatography , inorganic chemistry , alkyl
The pentafluorosulfanyl (SF 5 ) functional group was investigated from an environmental perspective to ascertain its physical properties and photolytic fate. Five aromatic probe compounds were compared with their trifluoromethyl analogs. Water solubilities for SF 5 compounds ranged from 78 mg/L to 2.4 g/L. Octanol—water partitioning coefficients ranged from log K ow = 2.9 to 3.6, all of which were approximately 0.5 to 0.6 log units more hydrophobic than their trifluoromethyl analogs. The direct photolytic fate of SF 5 compounds was studied, and the SF 5 group was found to completely degrade using actinic radiation with hourly half‐lives. The reaction was followed by high‐performance liquid chromatography with a UV‐visible detector, 19 F nuclear magnetic resonance spectroscopy, and high‐resolution mass spectrometry. It was found that five equivalents of fluoride were released to form a benzenesulfonate as a final product of photodegradation. Finally, an SF 5 analog of fluometuron, a potentially new herbicide, was synthesized and likewise photolyzed. The present study provides the first evidence that pentafluorosulfanyl can degrade under mild, environmentally relevant conditions.