The interaction of monosubstituted benzenes with the stationary liquid in gas liquid chromatography.
In gas liquid chromatography (GLC), the relative retention values log gamma was mainly expressed by van der Waals energy (the sum of the dispersion E(dis) and repulsive E(rep) energies) to the interactions between monosubstituted benzene derivatives and the nonpolar stationary liquid as squalane. The single exception was that of anilines, and it was corrected by the electrostatic energy (E(ES)) due to C-H/pi hydrogen bond. When the stationary liquid changed from the nonpolar to polar, log gamma was estimated by the inductive interaction energy (included in E(ES)) in addition to the sum of E(dis) and E(rep). In the benzene solution, the relative equilibrium values log K/K(o) introduced from the interactions between phenol and substituted benzene derivatives were estimated by E(ES). The E(ES) of COCH(3), CO(2)C(2)H(5) groups is especially originated in the excited dipole moments micro(e). The relative frequency values log nu/nu(o) derived from O-H or O-D stretching vibration of phenol or methanol-D gave the correlation to E(ES) as well as log K/K(o). That of anilines-methanol-D however had been out of a linear relation to E(ES). The cause is concluded that the aniline-methanol-D is making the proton transfer structure from the discussion about the proton affinity (PA) of the base.
Kawaki
Hideko
H
Pharmaceutical Research and Technology Institute, Kinki University, Higashi-Osaka, Japan. kawaki@msa.kindai.ac.jp
D001555:Benzene Derivatives / Q000737:chemistry*; D002251:Carbon Tetrachloride / Q000737:chemistry; D002849:Chromatography, Gas; D006860:Hydrogen Bonding; D000432:Methanol / Q000737:chemistry; D019800:Phenol / Q000737:chemistry; D013185:Squalene / Q000031:analogs & derivatives* / Q000737:chemistry*; D013816:Thermodynamics
D001555:Benzene Derivatives; D019800:Phenol; D013185:Squalene; D002251:Carbon Tetrachloride; C019556:squalane; D000432:Methanol