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

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

doi:10.1002/mrc.4085

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

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

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

4 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 language	English
Pages (from-to)	440-447
Journal	Magnetic Resonance in Chemistry
Volume	52
Issue number	8
DOIs	https://doi.org/10.1002/mrc.4085
Publication status	Published - 1 Jan 2014

Keywords

alfentanil
conformational analysis
DFT
molecular mechanics
NMR
transannular interactions

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10.1002/mrc.4085

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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 {\textcopyright} 2014 John Wiley & Sons, Ltd.",

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AU - Jaime, Carlos

AU - Virgili, Albert

AU - Portillo, Susana

AU - Caparrõs, Antoni

AU - Burusco, Kepa K.

PY - 2014/1/1

Y1 - 2014/1/1

N2 - 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.

AB - 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.

KW - alfentanil

KW - conformational analysis

KW - DFT

KW - molecular mechanics

KW - NMR

KW - transannular interactions

U2 - 10.1002/mrc.4085

DO - 10.1002/mrc.4085

M3 - Article

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VL - 52

SP - 440

EP - 447

JO - Magnetic Resonance in Chemistry

JF - Magnetic Resonance in Chemistry

IS - 8

ER -

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

Abstract

Keywords

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