A structural analysis of the complexes of (S, S)-dimethylpyridino-18-crown-6 with (R) and (S)-[α-(1-naphthyl)ethyl]ammonium perchlorate by NMR techniques and molecular modeling

Tingmin Wang, Jerald S. Bradshaw, Janet C. Curtis, Peter Huszthy, Reed M. Izatt

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Significant π-π interaction is found in the complexes of (S, S)-dimethylpyridino-18-crown-6 with (R)- and (S)-[α-(1-naphthyl)ethyl]ammonium perchlorate. This finding is supported by the1H NOESY NMR spectral technique, greater chemical shift changes of aromatic protons in both host and guest molecules upon complexation, and by molecular mechanics calculations. Because of the flexibility of the ligand, the tripod hydrogen bonding causes13C relaxation times of all periphery carbons to decrease without significant selectivity. Rotational energy barrier calculations of the methyl groups of the complexed ligand also show that the (S, S)-host-(R)-guest is the more stable complex.

Original languageEnglish
Pages (from-to)113-122
Number of pages10
JournalJournal of Inclusion Phenomena and Molecular Recognition in Chemistry
Volume16
Issue number2
DOIs
Publication statusPublished - Jun 1 1993

Keywords

  • NOESY
  • chemical shift
  • molecular mechanics calculation
  • relaxation time
  • tripod hydrogen bonding
  • π-π interaction

ASJC Scopus subject areas

  • Food Science
  • Chemistry(all)
  • Condensed Matter Physics

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