A computational and spectroscopic study of the gas-phase conformers of adrenaline

Pierre Çarçabal, Lavina C. Snoek, Tanja Van Mourik

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)

Abstract

The conformational landscapes of the neurotransmitter 1-adrenaline (1-epinephrine) and its diastereoisomer pseudo-adrenaline, isolated in the gas phase and un-protonated, have been investigated by using a combination of mass-selected ultraviolet and infrared holeburn spectroscopy, following laser desorption of the sample into a pulsed supersonic argon jet, and DFT and ab initio computation (at the B3LYP/6-31+G*, MP2/6-31+G* and MP2/aug-cc-pVDZ levels of theory). Both for adrenaline and its diastereoisomer, pseudo-adrenaline, one dominant molecular conformation, very similar to the one seen in noradrenaline, has been observed. It could be assigned to an extended side-chain structure (AG1a) stabilized by an OH -> N intramolecular hydrogen bond. An intramolecular hydrogen bond is also formed between the neighbouring hydroxyl groups on the catechol ring. The presence of further conformers for both diastereoisomers could not be excluded, but overlapping electronic spectra and low ion signals prevented further assignments.

Original languageEnglish
Pages (from-to)1633-1639
Number of pages7
JournalMolecular Physics
Volume103
Issue number11-12
DOIs
Publication statusPublished - 10 Jun 2005

Keywords

  • ION DIP SPECTROSCOPY
  • CONFORMATIONAL PREFERENCES
  • NORADRENALINE ANALOG
  • NEUROTRANSMITTERS
  • CATECHOL
  • CLUSTERS
  • S-0
  • VIBRATIONS
  • STATES

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