Synthesis of Monothiacalix[4]arene Using the Fragment Condensation Approach
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F25%3A43932855" target="_blank" >RIV/60461373:22310/25:43932855 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22810/25:43932855
Result on the web
<a href="https://www.mdpi.com/1420-3049/30/15/3145" target="_blank" >https://www.mdpi.com/1420-3049/30/15/3145</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3390/molecules30153145" target="_blank" >10.3390/molecules30153145</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis of Monothiacalix[4]arene Using the Fragment Condensation Approach
Original language description
The article describes a simple and scalable preparation of 2-monothiacalix[4]arene 7, the simplest representative of the mixed-bridged (CH<inf>2</inf> and S) calix[4]arenes. The synthesis is based on the condensation of linear building blocks (bisphenols), which are relatively readily available, and allows, depending on the conditions, the use of two alternative reaction routes that provide macrocycle 7 in high yield. The dynamic behavior of the basic macrocyclic skeleton was investigated using NMR spectroscopy at variable temperatures. High-temperature measurements showed that compound 7 undergoes a cone–cone equilibrium with activation free energy ΔG# of the inversion process of 63 kJ·mol−1. Interestingly, the same barrier for the oxidized sulfone derivative 14 shows a value of 60 kJ·mol−1, indicating weakened hydrogen bonds at the lower rim of the calixarene. The same was also confirmed at low temperatures, when barriers to changing the direction of the cyclic hydrogen bond arrays (flip-flop mechanism) were determined (compare ΔG# = 44 kJ·mol−1 for 7 vs. ΔG# = 40 kJ·mol−1 for 14). © 2025 by the authors.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
MOLECULES
ISSN
1420-3049
e-ISSN
1420-3049
Volume of the periodical
30
Issue of the periodical within the volume
15
Country of publishing house
CH - SWITZERLAND
Number of pages
15
Pages from-to
"27 July 2025"
UT code for WoS article
001549453400001
EID of the result in the Scopus database
2-s2.0-105013297852