13C GIAO DFT calculation as a tool for configuration prediction of N-O group in saturated heterocyclic N-oxides

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F12%3A00378932" target="_blank" >RIV/61388963:_____/12:00378932 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1002/mrc.3810" target="_blank" >http://dx.doi.org/10.1002/mrc.3810</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/mrc.3810" target="_blank" >10.1002/mrc.3810</a>

Result language

angličtina

Original language name

13C GIAO DFT calculation as a tool for configuration prediction of N-O group in saturated heterocyclic N-oxides

Original language description

Tropane, tropinone, pseudopelletierine and cocaine were oxidized in situ in a nuclear magnetic resonance (NMR) tube providing mixtures of exo/endo N-oxides. Observed 13C chemical shifts were correlated with values calculated by gauge-including atomic orbitals density functional theory (DFT) OPBE/6-31G method using DFT B3LYP/6-31G optimized geometries. The same method of 13C chemical shift calculation was applied on series of methyl-substituted 1-methylpiperidines and their epimeric N-oxides described inliterature. The results show that using this undemanding calculation method enables assignment of configuration of NO group in N-epimeric saturated heterocyclic N-oxides. The approach enables assigning of the configuration with high degree of certaintyeven if NMR data of only one isomer are available. An improved method of in situ oxidation of starting amines in an NMR tube is also described.

Czech name

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Czech description

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Type

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

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

<a href="/en/project/GA203%2F09%2F1919" target="_blank" >GA203/09/1919: Development of methods for configuration determination at chiral sulfur, nitrogen or phosphorus atom using NMR spectroscopy and ab initio calculations</a><br>

Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2012

Confidentiality

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

Name of the periodical

Magnetic Resonance in Chemistry

ISSN

0749-1581

e-ISSN

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Volume of the periodical

50

Issue of the periodical within the volume

6

Country of publishing house

GB - UNITED KINGDOM

Number of pages

9

Pages from-to

415-423

UT code for WoS article

000304086100002

EID of the result in the Scopus database

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