Enantiodiscrimination in NMR spectra and X-ray structures of diastereomeric salts of trans-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine with (S)-Mosher acid

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F02%3A00007020" target="_blank" >RIV/00216224:14310/02:00007020 - isvavai.cz</a>

Result on the web

—

DOI - Digital Object Identifier

—

Result language

angličtina

Original language name

Enantiodiscrimination in NMR spectra and X-ray structures of diastereomeric salts of trans-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine with (S)-Mosher acid

Original language description

Signal anisochrony delta in NMR spectra of racemic trans-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine 1 induced on the formation of diastereomeric salt complexes with (S)-Mosher acid 2 showed a strong dependence on solvent polarity, concentration, stoichiometric ratio and enantiomeric composition. X-ray structures of the salts, 3a and 3b, revealed that the conformations of the protonated base in ion pairs are very similar with respect to interatomic distances, bond and torsion angles but the mutual orientation of counterions in ion pairs differs significantly. It is suggested that the conformations of transient diastereomeric complexes in solution, responsible for delta;, resemble those in solid state. Furthermore, ab initio calculations performed on the optimized X-ray geometries of both ion pairs showed that the free energy of 3a is lower than that of 3b. This implies that the association constant for the formation of 3a is higher than that of 3b.

Czech name

—

Czech description

—

Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

—

Project

—

Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2002

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

J. Chem. Soc. Perkin Trans. 2

ISSN

1472-779X

e-ISSN

—

Volume of the periodical

2002

Issue of the periodical within the volume

12

Country of publishing house

CZ - CZECH REPUBLIC

Number of pages

7

Pages from-to

2093

UT code for WoS article

—

EID of the result in the Scopus database

—