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

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.