Phenyl-(2-pyridyl)-(3-pyridyl)-(4-pyridyl)methane: synthesis, chiroptical properties, and theoretical calculation of its absolute configuration

Chem Asian J. 2007 Aug 3;2(8):1031-6. doi: 10.1002/asia.200700141.

Abstract

The title compound, a prototypical chiral molecule based on a tetraarylmethane framework, has been synthesized in five steps from (2-pyridyl)-(3-pyridyl)ketone. X-ray crystallographic analysis revealed the tetraarylmethane framework of the molecule but did not determine the positions of the nitrogen atoms because the crystal is a racemic compound and the aryl groups are disordered in the crystal. The optical resolution of the title compound was achieved by chiral HPLC with a Chiralcel OD column. The CD spectra of the two fractions in acetonitrile exhibited opposite signs as expected for a pair of enantiomers. Their CD spectra are changed in 2 M HCl due to protonation. The calculated CD curve for the target molecule based on time-dependent density functional theory (TDDFT) reproduces the experimental result very well, thus suggesting that the first eluted fraction is the R isomer in terms of absolute configuration.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Circular Dichroism
  • Crystallography, X-Ray
  • Models, Molecular
  • Pyridines / chemistry*
  • Stereoisomerism*

Substances

  • Pyridines