Structure elucidation of phenoxathiin-based thiacalix[4]arene conformations using NOE and RDC data

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F18%3A43916444" target="_blank" >RIV/60461373:22310/18:43916444 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22810/18:43916444

Výsledek na webu

<a href="https://reader.elsevier.com/reader/sd/pii/S0040402018300425?token=F0071DFA124CF5169CAFF112E9AE7ACA2E0D18378AF1AD4255DD86C0BB195B4D8394F928BD5ACAA5EB14E140B4BED0B3" target="_blank" >https://reader.elsevier.com/reader/sd/pii/S0040402018300425?token=F0071DFA124CF5169CAFF112E9AE7ACA2E0D18378AF1AD4255DD86C0BB195B4D8394F928BD5ACAA5EB14E140B4BED0B3</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.tet.2018.01.020" target="_blank" >10.1016/j.tet.2018.01.020</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Structure elucidation of phenoxathiin-based thiacalix[4]arene conformations using NOE and RDC data

Popis výsledku v původním jazyce

Phenoxathiin-based thiacalix[4]arene, obtained by the acid-catalysed rearrangement of the corresponding spirodienone derivative, was immobilized using the alkylation with chloroacetonitrile to yield three (out of four theoretically possible) stereoisomers. As the conformational outcome of the reaction could not be unambiguously assigned using standard NMR techniques, the method of Residual Dipolar Coupling constants (RDCs) was applied. The measuring of an anisotropic through-space dipole-dipole interactions in the lyotropic liquid crystalline alignment medium (PELG, poly-gamma-ethyl-L-glutamate, and PBLG, poly-gamma-benzyl-L-glutamate) enabled the assignment of the individual conformers. The usefulness of this approach was finally confirmed by the X-ray crystallography data. (C) 2018 Elsevier Ltd. All rights reserved.

Název v anglickém jazyce

Structure elucidation of phenoxathiin-based thiacalix[4]arene conformations using NOE and RDC data

Popis výsledku anglicky

Phenoxathiin-based thiacalix[4]arene, obtained by the acid-catalysed rearrangement of the corresponding spirodienone derivative, was immobilized using the alkylation with chloroacetonitrile to yield three (out of four theoretically possible) stereoisomers. As the conformational outcome of the reaction could not be unambiguously assigned using standard NMR techniques, the method of Residual Dipolar Coupling constants (RDCs) was applied. The measuring of an anisotropic through-space dipole-dipole interactions in the lyotropic liquid crystalline alignment medium (PELG, poly-gamma-ethyl-L-glutamate, and PBLG, poly-gamma-benzyl-L-glutamate) enabled the assignment of the individual conformers. The usefulness of this approach was finally confirmed by the X-ray crystallography data. (C) 2018 Elsevier Ltd. All rights reserved.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA15-17572S" target="_blank" >GA15-17572S: Glykoklastry kalix[4]aren/C-oligosacharidy pro studium selektivity interakcí s lektiny</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2018

Kód důvěrnosti údajů

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

Název periodika

Tetrahedron

ISSN

0040-4020

e-ISSN

—

Svazek periodika

74

Číslo periodika v rámci svazku

8

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

6

Strana od-do

902-907

Kód UT WoS článku

000425197700014

EID výsledku v databázi Scopus

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