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Issue 19, 2000
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The complex chemistry of N-(phosphonomethyl)glycine (glyphosate): preparation and characterization of the ammonium, lithium, sodium (4 polymorphs) and silver(I) complexes

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Abstract

A series of complexes with the herbicide glyphosate [N-(phosphonomethyl)glycine = H3L] has been synthesized and characterized using infrared spectroscopy, and in the case of five of these, by single crystal X-ray diffraction. The compounds are ammonium glyphosate [NH4][H2L] 1, lithium glyphosate Li(H2L) 2, sodium glyphosate hemi-hydrate Na(H2L)·0.5H2O 3, sodium glyphosate monohydrate Na(H2L)·H2O 4, sodium glyphosate dihydrate Na(H2L)·2H2O 5, disodium glyphosate nonahydrate Na2(HL)·9H2O 6 and disilver glyphosate Ag2(HL) 7. The crystal structures of 1, 3, 4, 6 and 7 have been determined. Compound 1 consists of a hydrogen-bonded lattice structure in which all of the available ammonium protons are involved in hydrogen bonding, together with the zwitterionic amine group and the single phosphonate proton. Compounds 3 and 4 are both polymeric and based on dimeric repeating units with six-co-ordinate sodium centres. Complex 6 is based on both discrete octahedral [Na(HL)(H2O)5] anionic complex units with the unidentate glyphosate ligand bonded via a carboxylate oxygen, together with a cationic [Na2(H2O)8]2+ ribbon polymer. All structures have extensive hydrogen bonding interactions. The silver complex 7 is a polymer structure which involves the phosphonate ligands in linear chains joined through the carboxyl group at one end (via bis-O,O′ bridged silver dimers) and silver co-ordinated phosphonate oxygens at the other.

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Publication details

The article was received on 06 Apr 2000, accepted on 31 Jul 2000 and first published on 13 Sep 2000


Article type: Paper
DOI: 10.1039/B002748K
Citation: J. Chem. Soc., Dalton Trans., 2000,0, 3404-3410
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    The complex chemistry of N-(phosphonomethyl)glycine (glyphosate): preparation and characterization of the ammonium, lithium, sodium (4 polymorphs) and silver(I) complexes

    D. S. Sagatys, C. Dahlgren, G. Smith, R. C. Bott and J. M. White, J. Chem. Soc., Dalton Trans., 2000, 0, 3404
    DOI: 10.1039/B002748K

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