Dipolar compounds

{
  "id": "MLC-T-CHM-003237",
  "term": "Dipolar compounds",
  "field": "Chemistry",
  "definition": "Neutral molecules whose principal Lewis or resonance structures show one atom bearing a positive and another a negative formal charge, as in ylides, nitrones, azides, and diazo compounds. The charges are usually delocalized, but the term also covers species where they are not, and it is narrower than polar, since hydrogen chloride has a dipole moment but no formal charges. In 1,3-dipolar compounds the opposite charges lie on atoms 1 and 3 of a three-atom unit.",
  "subject": "Organic and Biomolecular Chemistry",
  "see_also": [
    "acyl carbenes",
    "azides",
    "azo imides",
    "azomethine imides",
    "azomethine ylides",
    "azoxy compounds",
    "betaines",
    "carbonyl imides",
    "carbonyl oxides",
    "carbonyl ylides",
    "diazo compounds",
    "imidoyl carbenes",
    "nitrile imides",
    "nitrile oxides",
    "nitrile ylides",
    "nitrilium betaines",
    "nitro compounds",
    "nitrones",
    "resonance",
    "vinyl carbenes"
  ],
  "references": [
    "PAC, 1995, 67, 1307. 'Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)' on page 1333 (https://doi.org/10.1351/pac199567081307)"
  ],
  "url": "https://mlchart.com/terminology/chemistry/dipolar-compounds/"
}