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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 38, Number 8
JKCSEZ 38(8)
April 20, 1994 

 
Title
Effect of Substituted Groups on the Retention of Monosubstituted Phenols in Reversed-Phase Liquid Chromatography

역상 액체 크로마토그래피에서 페놀 일치환체들의 머무름에 미치는 치환기들의 영향
Author
Hoon-Joo Kim, In-Ho Lee, dai Woon Lee

김훈주, 이인호, 이대운
Keywords
Abstract
C18 및 Phenyl 컬럼에서 메탄올-물 및 아세토니트릴-물 혼합액을 이동상으로 하여 21종의 페놀일치환체들의 머무름을 조사하여 치환기가 머무름에 미치는 영향을 알아보았다. 아미노페놀을 제외한 모든 시료의 머무름은 Phenyl 컬럼보다 C18 컬럼에서 더 컸으며, 두 이동상에 대해서는 물의 부피퍼센트가 같을때 메탄올계에서 더 컸다. 일반적으로 일치환 페놀류의 파라 이성질체는 메타 이성질체보다 빨리 용리되었고, 오르토와 메타 이성질체 사이에서는 용리순서가 치환기의 극성에 따라 다르게 나타났다. 페놀 일치환체들의 머무름은 시료와 미반응된 실란올과의 상호작용의 영향을 받는대 이러한 미반응된 실란올의 영향은 치환기의 hydrogen bonding acceptor basicity(β)가 클수록 크게 나타났고 Phenyl 컬럼보다 C18 컬럼에서 이들의 영향이 크게 나타났다. 시료의 van der Waals volume(VWV)과 β값을 함께 고려한 파라미터 (1.01VWV/100-1.84β)와 시료의 머무름(log k')과는 좋은 직선관계가 있다. 따라서 C18 및 Phenyl 컬럼에서 페놀 일치환체들의 머무름은 시료의 (1.01VWV/100-1.84β)값으로 쉽게 예측할 수 있음을 알았다.

The retention data of twenty one monosubstituted phenols in the eluent systems containing 30∼70% of methanol or acetonitrile as organic modifiers, on C18 and Phenyl columns were collected to investigate the effect of the substituted groups on the retention of phenols. The capacity factors of the solutes except amino phenols are greater on C18 than on Phenyl column. And all the solutes have shown greater capacity factors in methanol-water than that in acetonitrile-water as a mobile phase. Generally the elution order between meta and para isomers of monosubstituted phenols in consistent (p < m) regardless of the polarity of the substituted group. But the elution order between ortho and meta isomers of phenol varies with regard to the polarity of the substituted group. The retention of the monosubstituted phenols has been influenced by the interaction between the solute and unreacted silanol of columns as well as the interaction between the solute and C18 or phenyl group of columns. And then, the effect of unreacted silanol on the retention of the monosubstituted phenols is greater on C18 than on Phenyl column. And the greater hydrogen bonding acceptor basicity(β) of the substituted group is, the greater this effect is. The relationship between the retention of the monosubstituted phenols and their parameters such as van der Waals volume(VWV) and hydrogen bonding acceptor basicity(β) has been investigated. The good linearity has been observed in the plot log k' vs. (1.01VWV/100-1.84β). In consequence, the retention of the monosubstituted phenols on C18 and Phenyl columns can be easily predicted by the parameter (1.01VWV/100-1.84β).

Page
562 - 569
Full Text
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