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Issue 11, 2015
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A study on fluoride detection and assembly of hydroxyaromatic aldoximes caused by tetrabutylammonium fluoride

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Abstract

Tetrabutylammonium fluoride (TBAF) forms cocrystal H2NAP·TBAF with 2-hydroxynaphthaldoxime (H2NAP) or cocrystal 2(H3OHPA)·TBAF with 2,3-dihydroxyphenylaldoxime (H3OHPA), whereas a similar reaction with 2,4-dihydroxyphenylaldoxime (H3PHPA) forms tetrabutylammonium (TBA) salt TBA(H2.5PHPA)2. Formation of these cocrystals or salts is accompanied by a color change which enables the detection of fluoride ions. Cocrystal H2NAP·TBAF has a layered structure formed by hydrogen bonds between the fluoride ions and parent oxime molecules; the tetrabutylammonium cations are held in between layers of anionic assemblies. On the other hand, cocrystal 2(H3OHPA)·TBAF has a grid-like architecture constructed from hydrogen bonds between the parent oxime molecules and fluoride ions. TBA cations are encapsulated within the grids. It is shown that salt TBA(H2.5PHPA)2 forms anionic assemblies to encapsulate tetrabutylammonium cations which are devoid of fluoride ions. By interactions of the tetrabutylammonium fluoride ions with H3PHPA molecules, an anionic assembly is formed by the sharing of protons, which possesses a grid-like structure. The formation of such an assembly causes color change which enables one to detect fluoride ions by visual means.

Graphical abstract: A study on fluoride detection and assembly of hydroxyaromatic aldoximes caused by tetrabutylammonium fluoride

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The article was received on 21 Nov 2014, accepted on 03 Feb 2015 and first published on 05 Feb 2015


Article type: Paper
DOI: 10.1039/C4CE02311K
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Citation: CrystEngComm, 2015,17, 2301-2309
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    A study on fluoride detection and assembly of hydroxyaromatic aldoximes caused by tetrabutylammonium fluoride

    A. Tarai and J. B. Baruah, CrystEngComm, 2015, 17, 2301
    DOI: 10.1039/C4CE02311K

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