Pseudo acids

{
  "id": "MLC-T-CHM-009623",
  "term": "Pseudo acids",
  "field": "Chemistry",
  "definition": "A compound that shows ordinary acidic behaviour only after a slow structural rearrangement, usually tautomerization, so its ionization is far slower than a normal proton transfer. Nitroalkanes are the classic case: the neutral nitro form loses its carbon-bound proton slowly to give the nitronate anion, whereas the aci-nitro tautomer, a true acid, ionizes at once. Nitromethane has a pKa near 10 in water, while its aci form is near 3.",
  "subject": "Organic and Biomolecular Chemistry",
  "see_also": [
    "activation",
    "tautomerization"
  ],
  "references": [
    "PAC, 1995, 67, 1307. 'Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)' on page 1361 (https://doi.org/10.1351/pac199567081307)"
  ],
  "url": "https://mlchart.com/terminology/chemistry/pseudo-acids/"
}