Enantiomeric recognition of chiral ammonium salts by chiral pyridino- and pyrimidino-18-crown-6 ligands

Effect of structure and solvents

Jerald S. Bradshaw, P. Huszthy, J. Ty Redd, Xian Xin Zhang, Tingmin Wang, Jon K. Hathaway, Jolene Young, Reed M. Izatt

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Chiral pyridino-18-crown-6 ligands interact with chiral primary organic ammonium salts by hydrogen bonding from the ammonium cation to the pyridino nitrogen and two alternate ring oxygen atoms. Enantiomeric recognition in these interactions are caused by the steric bulk of the substituents at chiral macrocycle ring positions. Recognition is best for the interaction of chiral pyridino-18-crown-6 hosts with the enantiomers of α-(l-naphthylethyl)ammonium perchlorate (NapEtHClO4) over (α-phenylethyl)ammonium perchlorate (PhEtHC104) possibly because of a greater π-π overlap between the naphthalene ring of the guest and pyridine ring of the host. Solvents play an important role in the degree of recognition. A binary solvent composed of 7/3 C2H4Cl2/CH3OH (v/v) gave an enhanced degree of recognition. A new chiral pyrimidino-18-crown-6 ligand exhibited recognition for the enantiomers of NapEtHClO4.

Original languageEnglish
Pages (from-to)691-695
Number of pages5
JournalPure and Applied Chemistry
Volume67
Issue number5
DOIs
Publication statusPublished - Jan 1 1995

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Enantiomers
Ammonium Compounds
Salts
Ligands
Naphthalene
Pyridine
Hydrogen bonds
Positive ions
Nitrogen
Atoms
Oxygen
Cations
18-crown-6
ammonium perchlorate

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

Enantiomeric recognition of chiral ammonium salts by chiral pyridino- and pyrimidino-18-crown-6 ligands : Effect of structure and solvents. / Bradshaw, Jerald S.; Huszthy, P.; Redd, J. Ty; Zhang, Xian Xin; Wang, Tingmin; Hathaway, Jon K.; Young, Jolene; Izatt, Reed M.

In: Pure and Applied Chemistry, Vol. 67, No. 5, 01.01.1995, p. 691-695.

Research output: Contribution to journalArticle

Bradshaw, Jerald S. ; Huszthy, P. ; Redd, J. Ty ; Zhang, Xian Xin ; Wang, Tingmin ; Hathaway, Jon K. ; Young, Jolene ; Izatt, Reed M. / Enantiomeric recognition of chiral ammonium salts by chiral pyridino- and pyrimidino-18-crown-6 ligands : Effect of structure and solvents. In: Pure and Applied Chemistry. 1995 ; Vol. 67, No. 5. pp. 691-695.
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