Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Regular Articles
The Interaction of Monosubstituted Benzenes with the Stationary Liquid in Gas Liquid Chromatography
Hideko Kawaki
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2004 年 52 巻 2 号 p. 221-225

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In gas liquid chromatography (GLC), the relative retention values log γ was mainly expressed by van der Waals energy (the sum of the dispersion Edis and repulsive Erep 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 (EES) due to C–H/π hydrogen bond. When the stationary liquid changed from the nonpolar to polar, log γ was estimated by the inductive interaction energy (included in EES) in addition to the sum of Edis and Erep. In the benzene solution, the relative equilibrium values log K/Ko introduced from the interactions between phenol and substituted benzene derivatives were estimated by EES. The EES of COCH3, CO2C2H5 groups is especially originated in the excited dipole moments μe. The relative frequency values log ν/νo derived from O–H or O–D stretching vibration of phenol or methanol-D gave the correlation to EES as well as log K/Ko. That of anilines–methanol-D however had been out of a linear relation to EES. 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.
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© 2004 The Pharmaceutical Society of Japan
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