title: Phenyl-(2-pyridyl)-(3-pyridyl)-(4-pyridyl)methane: synthesis, chiroptical properties, and theoretical calculation of its absolute configuration.
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.
authors.affiliation: Graduate School of Science, Osaka University, 1-1 Machikaneyamacho, Toyonaka, Osaka 560-0043, Japan. kmatsu@chem.sci.osaka-u.ac.jp
authors.forename: Kouzou
authors.initials: K
authors.lastname: Matsumoto
authors.forename: Takuya
authors.initials: T
authors.lastname: Inagaki
authors.forename: Tatsuo
authors.initials: T
authors.lastname: Nehira
authors.forename: Masaki
authors.initials: M
authors.lastname: Kannami
authors.forename: Daisuke
authors.initials: D
authors.lastname: Inokuchi
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Kurata
authors.forename: Takeshi
authors.initials: T
authors.lastname: Kawase
authors.forename: Gennaro
authors.initials: G
authors.lastname: Pescitelli
authors.forename: Masaji
authors.initials: M
authors.lastname: Oda
mesh_terms: D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D011725:Pyridines