Chiral Pyridine-Based Macrobicyclic Clefts: Enantiomeric Recognition of Chiral Organic Ammonium Salts.

Abstract

Achiral macrobicyclic cleft containing a pyridine ring (1) formed a complex at 25 deg C in 50% CH3OH/50% CHCl3(v/v), with a primary ammonium salt (log K= 3.15) as evidenced by a significant change in the (1)H NMR spectrum. Highly organized pyridine-containing macrobicycle (S,S,S,S)-2 exhibited recognition at 25 deg C in 20% C2H5OH/80% 1,2-C2H4Cl2 (v/v) for the (S) enantiomer of alpha- (1-naphthyl)ethylammonium perchlorate (NapEt) over its (R) form (delta log K= 0.85). This high recognition factor probably reflects an increase in molecular rigidity by the introduction of a second macroring on the monocyclic pyridinocrown ligand.

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Document Details

Document Type
Technical Report
Publication Date
May 01, 1996
Accession Number
ADA309259

Entities

People

  • J. J. Young
  • Jerald S. Bradshaw
  • Paul C. Heller
  • Reed Izatt
  • Xian X. Zhang

Organizations

  • Brigham Young University

Tags

DTIC Thesaurus Topics

  • Abstracts
  • Ammonium Perchlorate
  • Chemical Compounds
  • Chemical Shifts
  • Chemical Synthesis
  • Chemistry
  • Chlorine Compounds
  • Enthalpy Changes
  • Governments
  • Military Research
  • Organic Compounds
  • Perchlorates
  • Physical Properties
  • Pyridines
  • Recognition
  • United States
  • United States Government

Fields of Study

  • Chemistry

Readers

  • Mathematics or Statistics
  • Organic Chemistry