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Issue 45, 2019
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Regioselective conversions of H4pdta (1,2-propanediaminetetraacetic acid) and H4eed3a to their triacetates on peroxotitanates

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Abstract

1,2-Propanediaminetetraacetic acid (H4pdta = C11H18O8N2) is degraded selectively to 1-methyl-1,2-propanediaminetriacetic acid (H3pd3a = C9H16O6N2) with a yield of 75% at room temperature, while N-(2-hydroxyethyl) ethylenediaminetriacetic acid (H4eed3a = C10H18O7N2) is converted with difficulty to ethylenediaminetriacetic acid (H3ed3a = C8H14O6N2) on peroxotitanates(IV), showing the influence of the uncoordinated leaving group. Various species in the reaction sequence are isolated and fully characterized, including (NH4)[Ti(O2)(Hpdta)]·H2O (1), (NH4)3[Ti(O2)(pdta)H(pdta)(O2)Ti]·7H2O (2), (NH4)[Ti(O2)(pd3a)]·H2O (3) and (NH4)[Ti(O2)(Heed3a)]·H2O (5). Peroxo dimer 2 forms a strong intramolecular hydrogen bond [2.451(3) Å] as an intermediate in the peroxo Ti-pdta system, which results in the absence of a fully deprotonated species of peroxo pdta titanate. A catalytic reaction of the peroxo titanate (NH4)3[Ti(O2)(pdta)H(pdta)(O2)Ti]·7H2O (2) for the conversion of pyridine to pyridine N-oxide shows 94% conversion at 80 °C.

Graphical abstract: Regioselective conversions of H4pdta (1,2-propanediaminetetraacetic acid) and H4eed3a to their triacetates on peroxotitanates

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Publication details

The article was received on 05 Sep 2019, accepted on 21 Oct 2019 and first published on 23 Oct 2019


Article type: Paper
DOI: 10.1039/C9DT03589C
Dalton Trans., 2019,48, 16943-16951

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    Regioselective conversions of H4pdta (1,2-propanediaminetetraacetic acid) and H4eed3a to their triacetates on peroxotitanates

    Y. Yang, Q. Liu, Z. Zhou and H. Wan, Dalton Trans., 2019, 48, 16943
    DOI: 10.1039/C9DT03589C

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