QUANTITATIVE STRUCTURE-RETENTION RELATIONSHIPS FOR SECONDARY INTERACTIONS IN CATION-EXCHANGE LIQUID-CHROMATOGRAPHY

被引:10
作者
LAW, B
WEIR, S
机构
[1] Zeneca Pharmaceuticals, Drug Kinetics Group, Safety of Medicines Department, Macclesfield, Cheshire SK10 4TG, Alderley Park
关键词
D O I
10.1016/0021-9673(93)83030-V
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Eighty-three aryl alkyl amines with a range of substituents in the aromatic ring were chromatographed on a silica stationary phase in the ion-exchange mode using a non-polar eluent which promotes hydrogen bonding interactions. The increase in retention due to the presence of the polar substituents was quantified using the functional group contribution value tau. The correlation between tau and a range of substituent physical and quantum chemical parameters was investigated using multiple regression. The increase in retention could be attributed to a hydrogen bonding interaction between the polar substituents and unionised silanols. This could be quantified in terms of the hydrogen bonding acceptor properties of the substituent (log K-beta) and it size, although the quality of the correlations was poor. A superior correlation was obtained using the lipophilicity (pi) of the substituent. The correlations, which gave an R(2) of 0.8423 at best were unsuited to accurate retention prediction.
引用
收藏
页码:17 / 24
页数:8
相关论文
共 14 条
[1]   HYDROGEN-BONDING .9. SOLUTE PROTON DONOR AND PROTON ACCEPTOR SCALES FOR USE IN DRUG DESIGN [J].
ABRAHAM, MH ;
DUCE, PP ;
PRIOR, DV ;
BARRATT, DG ;
MORRIS, JJ ;
TAYLOR, PJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (10) :1355-1375
[2]   SEPARATION OF ORGANIC AMINE COMPOUNDS ON SILICA-GEL WITH REVERSED-PHASE ELUENTS [J].
BIDLINGMEYER, BA ;
DELRIOS, JK ;
KORPI, J .
ANALYTICAL CHEMISTRY, 1982, 54 (03) :442-447
[3]   SURFACE SILANOLS IN SILICA-BONDED HYDROCARBONACEOUS STATIONARY PHASES .2. IRREGULAR RETENTION BEHAVIOR AND EFFECT OF SILANOL MASKING [J].
BIJ, KE ;
HORVATH, C ;
MELANDER, WR ;
NAHUM, A .
JOURNAL OF CHROMATOGRAPHY, 1981, 203 (JAN) :65-84
[4]  
Hansch C., 1979, SUBSTITUENT CONSTANT
[5]   FUNDAMENTAL-STUDIES IN REVERSED-PHASE LIQUID SOLID EXTRACTION OF BASIC DRUGS .2. HYDROGEN-BONDING EFFECTS [J].
LAW, B ;
WEIR, S .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 1992, 10 (2-3) :181-186
[6]   USE OF SILICA WITH REVERSED-PHASE TYPE ELUENTS FOR THE ANALYSIS OF BASIC DRUGS AND METABOLITES [J].
LAW, B .
TRAC-TRENDS IN ANALYTICAL CHEMISTRY, 1990, 9 (01) :31-36
[8]  
LAW B, UNPUB
[10]  
MORRIS JA, COMMUNICATION