Molecules (Jul 2023)

Ammonium <i>N</i>-(pyridin-2-ylmethyl)oxamate (AmPicOxam): A Novel Precursor of Calcium Oxalate Coating for Carbonate Stone Substrates

  • Anna Pintus,
  • M. Carla Aragoni,
  • Gianfranco Carcangiu,
  • Veronica Caria,
  • Simon J. Coles,
  • Eleanor Dodd,
  • Laura Giacopetti,
  • Domingo Gimeno,
  • Vito Lippolis,
  • Paola Meloni,
  • Simone Murgia,
  • Antonia Navarro Ezquerra,
  • Enrico Podda,
  • Claudia Urru,
  • Massimiliano Arca

DOI
https://doi.org/10.3390/molecules28155768
Journal volume & issue
Vol. 28, no. 15
p. 5768

Abstract

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Ammonium N-(pyridin-2-ylmethyl)oxamate (AmPicOxam), synthesized from O-methyl-N-(pyridin-2-ylmethyl)oxamate, was spectroscopically and structurally characterized and assayed as a novel precursor for the protection and consolidation of carbonate stone substrates. An in-depth characterization of treated and untreated biomicritic limestone and white Carrara marble samples was carried out by means of SEM microscopy, X-ray powder diffraction, helium pycnometry, determination of water transport properties, and pull-off tests. The improved solubility (1.00 M, 16.5% w/w) of the title compound with respect to ammonium oxalate (0.4 M, 5% w/w) results in the formation of a thicker protective coating of calcium oxalate (CaOx) dihydrate (weddellite) on marble and biomicrite samples after the treatment with 5% and 12% w/w water solutions, producing a reduction in the stone porosity and increased cohesion. Theoretical calculations were carried out at the DFT level to investigate both the electronic structure of the N-(pyridin-2-ylmethyl)oxamate anion and the hydrolysis reaction leading from AmPicOxam to CaOx.

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