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Issue 8, 2005
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Urea vs. thiourea in anion recognition

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Abstract

Neutral anion receptors (LH) form stable 1 : 1 H-bond [LH⋯X] complexes with carboxylates, halides and phosphate (X). Some of the [LH⋯X] complexes, in presence of an excess of X, release an HX fragment, with formation of [HX2] and the deprotonated receptor L. The tendency towards deprotonation increases with the acidity of the receptor and with the stability of the [HX2] self-complex. Thus, the more acidic thiourea containing receptor deprotonates in the presence all the investigated anions except chloride, whereas the less acidic urea containing receptor undergoes deprotonation only in the presence of fluoride, due to the high stability of [HF2].

Graphical abstract: Urea vs. thiourea in anion recognition

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Publication details

The article was received on 06 Jan 2005, accepted on 22 Feb 2005 and first published on 10 Mar 2005


Article type: Paper
DOI: 10.1039/B500123D
Citation: Org. Biomol. Chem., 2005,3, 1495-1500
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    Urea vs. thiourea in anion recognition

    D. E. Gómez, L. Fabbrizzi, M. Licchelli and E. Monzani, Org. Biomol. Chem., 2005, 3, 1495
    DOI: 10.1039/B500123D

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