Factors influencing enantiomeric recognition of primary alkylammonium salts by pyridino-18-crown-6 type ligands

Reed M. Izatt, Tingmin Wang, Jon K. Hathaway, Xian X. Zhang, Janet C. Curtis, Jerald S. Bradshaw, Cheng Y. Zhu, P. Huszthy

Research output: Contribution to journalArticle

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Abstract

Equilibrium constant (K), enthalpy change (ΔH), and entropy change (ΔS) values were determined for the interactions of a series of chiral pyridino-18-crown-6 type ligands with enantiomers of several primary alkylammonium salts in various solvents. Good enantiomeric recognition in terms of Δ log K was observed in many systems with Δ log K values greater than 0.4. The extent of enantiomeric recognition and the stabilities of the chiral crown ether-ammonium salt complexes were found to depend on the rigidity of the macrocyclic frame of the ligand, the type and arrangement of the donor atoms on the ligand, the bulkiness of the substituents on the ligand's chiral centers, the location of the chiral centers on the ligand, and the solvent. The effects of these factors on the extent of enantiomeric recognition and on the stabilities of the complexes were examined for the systems studied.

Original languageEnglish
Pages (from-to)157-175
Number of pages19
JournalJournal of Inclusion Phenomena and Molecular Recognition in Chemistry
Volume17
Issue number2
DOIs
Publication statusPublished - Jun 1994

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Salts
Ligands
salts
ligands
Crown Ethers
ammonium salts
Enantiomers
enantiomers
Equilibrium constants
Entropy
enthalpy
entropy
Ammonium Compounds
rigidity
Rigidity
ethers
Enthalpy
18-crown-6
Atoms
atoms

Keywords

  • Enantiomeric recognition
  • enthalpy change (ΔH)
  • entropy change (ΔS)
  • equilibrium constant (K)
  • NMR
  • primary alkylammonium salts
  • pyridino-18-crown-6 type ligands
  • titration calorimetry

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Chemistry(all)

Cite this

Factors influencing enantiomeric recognition of primary alkylammonium salts by pyridino-18-crown-6 type ligands. / Izatt, Reed M.; Wang, Tingmin; Hathaway, Jon K.; Zhang, Xian X.; Curtis, Janet C.; Bradshaw, Jerald S.; Zhu, Cheng Y.; Huszthy, P.

In: Journal of Inclusion Phenomena and Molecular Recognition in Chemistry, Vol. 17, No. 2, 06.1994, p. 157-175.

Research output: Contribution to journalArticle

Izatt, Reed M. ; Wang, Tingmin ; Hathaway, Jon K. ; Zhang, Xian X. ; Curtis, Janet C. ; Bradshaw, Jerald S. ; Zhu, Cheng Y. ; Huszthy, P. / Factors influencing enantiomeric recognition of primary alkylammonium salts by pyridino-18-crown-6 type ligands. In: Journal of Inclusion Phenomena and Molecular Recognition in Chemistry. 1994 ; Vol. 17, No. 2. pp. 157-175.
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AB - Equilibrium constant (K), enthalpy change (ΔH), and entropy change (ΔS) values were determined for the interactions of a series of chiral pyridino-18-crown-6 type ligands with enantiomers of several primary alkylammonium salts in various solvents. Good enantiomeric recognition in terms of Δ log K was observed in many systems with Δ log K values greater than 0.4. The extent of enantiomeric recognition and the stabilities of the chiral crown ether-ammonium salt complexes were found to depend on the rigidity of the macrocyclic frame of the ligand, the type and arrangement of the donor atoms on the ligand, the bulkiness of the substituents on the ligand's chiral centers, the location of the chiral centers on the ligand, and the solvent. The effects of these factors on the extent of enantiomeric recognition and on the stabilities of the complexes were examined for the systems studied.

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