Separation of planar rotamers through intramolecular hydrogen bonding in polysubstituted 5-nitrosopyrimidines

Chem Commun (Camb). 2014 Dec 7;50(94):14892-5. doi: 10.1039/c4cc06978a.

Abstract

While purifying new polysubstituted 5-nitrosopyrimidines, the unique separation of pairs of rotamers as chemical species, stabilized by a single intramolecular hydrogen bond and differing only in nitroso group orientation, was achieved. This interesting stereochemical phenomenon is compared to the well-known atropisomerism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydrogen Bonding
  • Nitroso Compounds / chemistry*
  • Pyrimidines / chemistry*
  • Stereoisomerism

Substances

  • Nitroso Compounds
  • Pyrimidines