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Zeitschrift für Physikalische Chemie

International journal of research in physical chemistry and chemical physics

Editor-in-Chief: Rademann, Klaus


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2196-7156
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Volume 225, Issue 2

Issues

Protonation of Benzo-18-crown-6: Extraction and DFT Study

Petr Toman
  • 1 Academy of Sciences of the Czech Republic, Institute of Macromolecular Chemistry, Prague 6, Tschechische Republik
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Emanuel Makrlík / Petr Vaňura
  • 2 Institute of Chemical Technology, Prague, Department of Analytical Chemistry, Prague 6, Tschechische Republik
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Vaclav Kašička
  • 3 Academy of Sciences of the Czech Republic, Institute of Organic Chemistry and Biochemistry, Prague, Tschechische Republik
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2010-12-09 | DOI: https://doi.org/10.1524/zpch.2011.0013

Abstract

From extraction experiments and γ-activity measurements, the extraction constant corresponding to the equilibrium H3O+(aq) + 1·Na+(nb)⇌1·H3O+(nb) + Na+(aq) taking place in the two-phase water-nitrobenzene system (1 = benzo-18-crown-6, aq = aqueous phase, nb = nitrobenzene phase) was evaluated as log Kex(H3O+, 1·Na+)=-0.8±0.1. Further, the stability constant of the 1·H3O+ complex in water-saturated nitrobenzene was calculated for a temperature of 25°C as log βnb(1·H3O+)=6.3±0.1. Finally, by using quantum mechanical DFT calculations, the most probable structure of the 1·H3O+ cationic complex species was derived. In this complex, the hydroxonium ion H3O+ is bound by three strong linear hydrogen bonds to one (Ar–O–CH2) ethereal oxygen and two (CH2–O–CH2) ethereal oxygen atoms of the parent crown ligand 1. The interaction energy was found to be -401.4kJ/mol, confirming the formation of the considered complex 1·H3O+.

Keywords: Protonation; Nitrobenzene; Benzo-18-crown-6; Extraction and Stability Constants; DFT

About the article

* Correspondence address: University of West Bohemia, Faculty of Applied Sciences, Husova 11, 306 14 Pilsen, Tschechische Republik,


Published Online: 2010-12-09

Published in Print: 2011-02-01


Citation Information: Zeitschrift für Physikalische Chemie, Volume 225, Issue 2, Pages 265–270, ISSN (Online) 2196-7156, ISSN (Print) 0942-9352, DOI: https://doi.org/10.1524/zpch.2011.0013.

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