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.
|Journal||Magnetic Resonance in Chemistry|
|Publication status||Published - 1 Jan 2014|
- conformational analysis
- molecular mechanics
- transannular interactions
Jaime, C., Virgili, A., Portillo, S., Caparrõs, A., & Burusco, K. K. (2014). Configuration and conformation of alfentanil hydrochloride. Conformational study by NMR and theoretical calculations. Magnetic Resonance in Chemistry, 52(8), 440-447. https://doi.org/10.1002/mrc.4085