Synthesis, experimental and theoretical studies on the factors influencing the pKa values of new crown ethers containing a diarylphosphinic acid unit

Tamás Szabó, Gergő Dargó, Hajnalka Szentjóbi, Tünde Tóth, Balázs Krámos, Richárd Izrael, Julianna Oláh, Tamás Németh, György T. Balogh, Péter Huszthy

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Synthesis of acidic new crown ethers containing a diarylphosphinic acid unit has been accomplished. The aromatic rings of the crown ethers were substituted with tert-butyl and nitro groups. Nitro substitution of the crown ethers was investigated. pKa determination of the new proton-ionizable crown ethers has been performed, showing the effect of the substituents of the aromatic rings on the acidity. An anomaly was discovered in the pKa values and an explanation was given based on quantum mechanical calculations and molecular dynamics simulations.

Original languageEnglish
Pages (from-to)8593-8602
Number of pages10
JournalTetrahedron
Volume72
Issue number52
DOIs
Publication statusPublished - Dec 29 2016

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Crown Ethers
Theoretical Models
Acids
Molecular Dynamics Simulation
Acidity
Molecular dynamics
Protons
Substitution reactions
Computer simulation

Keywords

  • Acidity
  • DFT, MD simulations
  • Diarylphosphinic acids
  • pK determination
  • Proton-ionizable crown ethers

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Synthesis, experimental and theoretical studies on the factors influencing the pKa values of new crown ethers containing a diarylphosphinic acid unit. / Szabó, Tamás; Dargó, Gergő; Szentjóbi, Hajnalka; Tóth, Tünde; Krámos, Balázs; Izrael, Richárd; Oláh, Julianna; Németh, Tamás; Balogh, György T.; Huszthy, Péter.

In: Tetrahedron, Vol. 72, No. 52, 29.12.2016, p. 8593-8602.

Research output: Contribution to journalArticle

Szabó, T, Dargó, G, Szentjóbi, H, Tóth, T, Krámos, B, Izrael, R, Oláh, J, Németh, T, Balogh, GT & Huszthy, P 2016, 'Synthesis, experimental and theoretical studies on the factors influencing the pKa values of new crown ethers containing a diarylphosphinic acid unit', Tetrahedron, vol. 72, no. 52, pp. 8593-8602. https://doi.org/10.1016/j.tet.2016.11.041
Szabó, Tamás ; Dargó, Gergő ; Szentjóbi, Hajnalka ; Tóth, Tünde ; Krámos, Balázs ; Izrael, Richárd ; Oláh, Julianna ; Németh, Tamás ; Balogh, György T. ; Huszthy, Péter. / Synthesis, experimental and theoretical studies on the factors influencing the pKa values of new crown ethers containing a diarylphosphinic acid unit. In: Tetrahedron. 2016 ; Vol. 72, No. 52. pp. 8593-8602.
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