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Cited by 260

The DOI matches its Crossref record; 32 of the 32 references it cites were found in a registry or an index.

Cationic Boranes for the Complexation of Fluoride Ions in Water below the 4 ppm Maximum Contaminant Level

Kim, Youngmin, Gabbaï, François P.·2009·Journal of the American Chemical Society
DOI 10.1021/ja8091467
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Abstract

In search of a molecular receptor that could bind fluoride ions in water below the maximum contaminant level of 4 ppm set by the Environmental Protection Agency (EPA), we have investigated the water stability and fluoride binding properties of a series of phosphonium boranes of general formula [p-(Mes(2)B)C(6)H(4)(PPh(2)R)](+) with R = Me ([1](+)), Et ([2](+)), n-Pr ([3](+)), and Ph ([4](+)). These phosphonium boranes are water stable and react reversibly with water to form the corresponding zwitterionic hydroxide complexes of general formula p-(Mes(2)(HO)B)C(6)H(4)(PPh(2)R). They also react with fluoride ions to form the corresponding zwitterionic fluoride complexes of general formula p-(Mes(2)(F)B)C(6)H(4)(PPh(2)R). Spectrophotometric acid-base titrations carried out in H(2)O/MeOH (9:1 vol.) afford pK(R+) values of 7.3(+/-0.07) for [1](+), 6.92(+/-0.1) for [2](+), 6.59(+/-0.08) for [3](+), and 6.08(+/-0.09) for [4](+), thereby indicating that the Lewis acidity of the cationic boranes increases in following order: [1](+) < [2](+) < [3](+) < [4](+). In agreement with this observation, fluoride titration experiments in H(2)O/MeOH (9:1 vol.) show that the fluoride binding constants (K = 840(+/-50) M(-1) for [1](+), 2500(+/-200) M(-1) for [2](+), 4000(+/-300) M(-1) for [3](+), and 10 500(+/-1000) M(-1) for [4](+)) increase in the same order. These results show that the Lewis acidity of the cationic boranes increases with their hydrophobicity. The resulting Lewis acidity increase is substantial and exceeds 1 order of magnitude on going from [1](+) to [4](+). In turn, [4](+) is sufficiently fluorophilic to bind fluoride ions below the EPA contaminant level in pure water. These results indicate that phosphonium boranes related to [4](+) could be used as molecular recognition units in chemosensors for drinking water analysis.

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Metadata

Authors
Kim, Y., & Gabbaï, F. P.
Venue
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Published
2009-02-11
Volume
131
Issue
9
Pages
3363-3369
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
DOI
10.1021/ja8091467
OpenAlex
W2041623685
Cited by
260
References
32
FWCI
12.77
Type
journal article
Language
en
Open access
closed

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