Crystal structures of crown ethers containing an alkyl diarylphosphinate or a diarylphosphinic acid unit

György Székely, Viktor Farkas, L. Párkányí, Tünde Tóth, M. Hollósi, P. Huszthy

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

This paper describes the structures of pseudo-18-crown-6 compounds (2, R,R-4 and 5) in the crystals together with theoretical calculations of the electronic circular dichroism (ECD) spectra. The achiral macrocyclic phosphinic acid 5 forms hydrogen-bonded dimers in the crystal. The O1-O2 distance (2.489 Ǻ) indicates strong H-bondings. The conformations of the macrorings of the achiral phosphinate 2 and the monomers of the achiral phosphinic acid 5 are chiral. A comparison of the torsion angles of the achiral methyl phosphinate 2 and the monomeric units of achiral 5 indicates a similar geometry. The torsion angles of the chiral methyl phosphinate (R,R)-4 differ more significantly from those in achiral methyl phosphinate 2. A negative 1Bb exciton couplet was observed in the ECD spectrum of monomeric (R,R)-6 in MeOH and H2O as in the spectra of (R,R)-4 in all solvents. To support the idea that (R,R)-4 has basically the same conformation in the crystal and in solution, the ECD spectrum of (R,R)-4 was calculated using the geometry of the molecule in the crystal. The calculated ECD spectrum shows a reasonable agreement with the ECD spectra obtained in solution. This shows that the steric structure observed in the crystal is predominant in solution as well.

Original languageEnglish
Pages (from-to)277-282
Number of pages6
JournalStructural Chemistry
Volume21
Issue number1
DOIs
Publication statusPublished - Feb 2010

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Crown Ethers
ethers
Crystal structure
dichroism
Phosphinic Acids
Crystals
acids
crystal structure
Acids
electronics
Torsional stress
crystals
Conformations
torsion
Geometry
Dimers
Hydrogen
geometry
Monomers
monomers

Keywords

  • Computed ECD spectra
  • Crown ethers
  • Diarylphosphinates
  • Diarylphosphinic acids
  • X-ray analysis

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

Cite this

Crystal structures of crown ethers containing an alkyl diarylphosphinate or a diarylphosphinic acid unit. / Székely, György; Farkas, Viktor; Párkányí, L.; Tóth, Tünde; Hollósi, M.; Huszthy, P.

In: Structural Chemistry, Vol. 21, No. 1, 02.2010, p. 277-282.

Research output: Contribution to journalArticle

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AB - This paper describes the structures of pseudo-18-crown-6 compounds (2, R,R-4 and 5) in the crystals together with theoretical calculations of the electronic circular dichroism (ECD) spectra. The achiral macrocyclic phosphinic acid 5 forms hydrogen-bonded dimers in the crystal. The O1-O2 distance (2.489 Ǻ) indicates strong H-bondings. The conformations of the macrorings of the achiral phosphinate 2 and the monomers of the achiral phosphinic acid 5 are chiral. A comparison of the torsion angles of the achiral methyl phosphinate 2 and the monomeric units of achiral 5 indicates a similar geometry. The torsion angles of the chiral methyl phosphinate (R,R)-4 differ more significantly from those in achiral methyl phosphinate 2. A negative 1Bb exciton couplet was observed in the ECD spectrum of monomeric (R,R)-6 in MeOH and H2O as in the spectra of (R,R)-4 in all solvents. To support the idea that (R,R)-4 has basically the same conformation in the crystal and in solution, the ECD spectrum of (R,R)-4 was calculated using the geometry of the molecule in the crystal. The calculated ECD spectrum shows a reasonable agreement with the ECD spectra obtained in solution. This shows that the steric structure observed in the crystal is predominant in solution as well.

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