Reactivity of N-nitrosoamides in confined spaces

Aaron C. Sather, Orion B. Berryman, Dariush Ajami, Julius Rebek

Research output: Contribution to journalArticlepeer-review

Abstract

The thermal rearrangement of several N-nitrosoamides was studied by 1H NMR in the context of reversible encapsulation. The N-nitrosoamide guests were isolated from the bulk solvent in a hydrogen-bonded dimeric host capsule which prevented their rearrangement. The guests appear to be preserved in their ground state conformations by the pressure exerted by the host. The conformations of the free and bound N-nitrosoamides are of comparable relative energies as determined by DFT calculations.

Original languageEnglish
Pages (from-to)2100-2103
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number17
DOIs
StatePublished - Apr 27 2011

Keywords

  • Hydrogen bonding
  • N-Nitrosoamides
  • Reversible encapsulation

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