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

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/60460709:41330/17:74568 RIV/60461373:22810/17:43903846

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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 &quot;central&quot; 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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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 &quot;central&quot; 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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10406 - Analytical chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2017

Kód důvěrnosti údajů

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

Název periodika

Journal of Molecular Structure

ISSN

0022-2860

e-ISSN

—

Svazek periodika

1134

Číslo periodika v rámci svazku

Neuvedeno

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

6

Strana od-do

722-727

Kód UT WoS článku

000394919100082

EID výsledku v databázi Scopus

2-s2.0-85009776749