Solvent-controlled formation of alkali and alkali-earth-secured cucurbituril/guest trimers
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F23%3A00575698" target="_blank" >RIV/61388963:_____/23:00575698 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/23:10469194
Result on the web
<a href="https://doi.org/10.1039/D3SC02032K" target="_blank" >https://doi.org/10.1039/D3SC02032K</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d3sc02032k" target="_blank" >10.1039/d3sc02032k</a>
Alternative languages
Result language
angličtina
Original language name
Solvent-controlled formation of alkali and alkali-earth-secured cucurbituril/guest trimers
Original language description
Cucurbit[7]uril (CB[7]) encapsulates adamantyl and trimethylsilyl substituents of positively charged guests in dimethyl sulfoxide (DMSO). Unlike in water or deuterium oxide, addition of a selection of alkali and alkali-earth cations with van der Waals radii between 1.0 and 1.4 Å (Na+, K+, Ca2+, Sr2+, Ba2+ and Eu3+) to the CB[7]/guest complexes triggers their cation-mediated trimerization, a process that is very slow on the nuclear magnetic resonance (NMR) time scale. Smaller (Li+, Mg2+) or larger cations (Rb+, Cs+ or NH4+) are inert. The trimers display extensive CH-O interactions between the equatorial and pseudo-equatorial hydrogens of CB[7] and the carbonyl rim of the neighboring CB[7] unit in the trimer, and a deeply nested cation between the three interacting carbonylated CB[7] rims, a counteranion is likely perched in the shallow cavity formed by the three outer walls of CB[7] in the trimer. Remarkably, a guest must occupy the cavity of CB[7] for trimerization to take place. Using a combination of semi-empirical and density functional theory techniques in conjunction with continuum solvation models, we showed that trimerization is favored in DMSO, and not in water, because the penalty for the partial desolvation of three of the six CB[7] portals upon aggregation into a trimer is less unfavorable in DMSO compared to water.
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
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chemical Science
ISSN
2041-6520
e-ISSN
2041-6539
Volume of the periodical
14
Issue of the periodical within the volume
35
Country of publishing house
GB - UNITED KINGDOM
Number of pages
9
Pages from-to
9258-9266
UT code for WoS article
001167938200001
EID of the result in the Scopus database
2-s2.0-85170240590