Configuration and conformation of alfentanil hydrochloride. Conformational study by NMR and theoretical calculations

Carlos Jaime, Albert Virgili, Susana Portillo, Antoni Caparrõs, Kepa K. Burusco

Research output: Contribution to journalArticleResearchpeer-review

2 Citations (Scopus)

Abstract

The configurational and conformational structure of alfentanil hydrochloride (1) was studied by nuclear magnetic resonance and theoretical calculations. Compound 1 is best described by equilibrium between two stereoisomeric piperidinium rings with the N-substituent always being in equatorial position. Nuclear magnetic resonance spectra demonstrate that, depending on the solvent, 1 adopts the conformation with an axial methoxymethylene group. Computations were crucial in determining the importance of the transannular attractive interaction between the positive charge at the piperidinium N-atom and the methoxymethyl group in position 4. Copyright © 2014 John Wiley & Sons, Ltd.
Original languageEnglish
Pages (from-to)440-447
JournalMagnetic Resonance in Chemistry
Volume52
Issue number8
DOIs
Publication statusPublished - 1 Jan 2014

Keywords

  • alfentanil
  • conformational analysis
  • DFT
  • molecular mechanics
  • NMR
  • transannular interactions

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