Protonation of calix[4]arene-(2,3-naphthylene-crown-6,crown-6): Experimental and theoretical study

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F17%3A43903846" target="_blank" >RIV/60461373:22340/17:43903846 - isvavai.cz</a>
Alternative codes found
RIV/60460709:41330/17:74568 RIV/60461373:22810/17:43903846
Result on the web
<a href="http://www.sciencedirect.com/science/article/pii/S0022286016313023" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0022286016313023</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.molstruc.2016.12.013" target="_blank" >10.1016/j.molstruc.2016.12.013</a>

Result language
angličtina
Original language name
Protonation of calix[4]arene-(2,3-naphthylene-crown-6,crown-6): Experimental and theoretical study
Original language description
On the basis of extraction experiments and gamma-activity measurements, the extraction constant corresponding to the equilibrium H3O+ (aq) + 1 center dot Na+ (nb) reversible arrow 1 center dot H3O+ (nb) + Na+ (aq) occurring in the two-phase water nitrobenzene system (1 = calix[4]arene-(2,3-naphthylene-crown-6,crown-6); aq = aqueous phase, nb = nitrobenzene phase) was determined as log K-ex(H3O+,1 center dot Na+) = -0.2 +/- 0.1. Further, the stability constant of the 1 center dot H3O+ complex in nitrobenzene saturated with water was calculated for a temperature of 25 degrees C: log beta(nb)(1 center dot H3O+) = 5.9 +/- 0.2. Finally, applying quantum chemical OFT calculations, the most probable structure of the cationic complex species 1 center dot H3O+ was derived. In the resulting complex, the "central" cation H3O+ is bound by three strong hydrogen bonds to two phenoxy oxygen atoms and to one ethereal oxygen from the crown-6 moiety of the parent ligand 1. The interaction energy, E(int), of the considered 1 center dot H3O+ complex was found to be -416.0 kJ/mol, confirming the formation of this cationic species as well.
Czech name
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Czech description
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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
10406 - Analytical chemistry

Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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