INTERMOLECULAR INTERACTIONS RESPONSIBLE FOR THE ABSENCE OF CHIRAL RECOGNITION - AROMATIC C-H...O HYDROGEN-BONDING IN THE CRYSTAL-STRUCTURE OF 3-CHLORO-9,13-DIBUTYLAMINO-1-HYDROXYPROPYL-6-TRIFLUOMETHYLPHENANTHRENE PROPAN-2-OL SOLVATE HYDROCHLORIDE

被引：8

作者：

CAMILLERI, P

EGGLESTON, DS

RZEPA, HS

WEBB, ML

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,KING OF PRUSSIA,PA 19406

[2] UNIV LONDON IMPERIAL COLL SCI & TECHNOL,DEPT CHEM,LONDON SW7 2AY,ENGLAND

[3] SMITHKLINE BEECHAM PHARMACEUT,TONBRIDGE TN11 9AN,KENT,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 09期

关键词：

D O I：

10.1039/c39940001135

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Both the 3-Cl and the more remote 6-CF3 groups in 1-dechlorohalofantrine 3 promote strong edge-to-edge aromatic O...H(1)-C interactions, similar to those found in thiamine picrate 6, which we suggest inhibit the resolution of 3 on chiral HPLC columns, whereas the 1-Cl substituent in halofantrine itself 2 blocks this interaction and allows resolution via chiral pi-pi face stacking.

引用

收藏

页码：1135 / 1137

页数：3

相关论文

共 20 条

[1] THE DEVELOPMENT OF VERSION-3 AND VERSION-4 OF THE CAMBRIDGE STRUCTURAL DATABASE SYSTEM [J].

ALLEN, FH ;

DAVIES, JE ;

GALLOY, JJ ;

JOHNSON, O ;

KENNARD, O ;

MACRAE, CF ;

MITCHELL, EM ;

MITCHELL, GF ;

SMITH, JM ;

WATSON, DG .

JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, 1991, 31 (02) :187-204

[2] CHIRAL SEPARATION OF THE OPTICAL ISOMERS OF THE ANTIMALARIAL DRUG HALOFANTRINE [J].

CAMILLERI, P ;

DYKE, C ;

HOSSNER, F .

JOURNAL OF CHROMATOGRAPHY, 1989, 477 (02) :471-473

[3] ARYL GROUP PI-FACIAL ELECTROSTATIC ASYMMETRY AS A CONTRIBUTING FACTOR TO CHIRAL RESOLUTION ON BETA-CYCLODEXTRIN HPLC PHASES [J].

CAMILLERI, P ;

EDWARDS, AJ ;

RZEPA, HS ;

GREEN, SM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (16) :1122-1124

[4] STRENGTH AND LINEARITY OF C-H=O BONDS IN MOLECULAR-CRYSTALS - A DATABASE STUDY OF SOME TERMINAL ALKYNES [J].

DESIRAJU, GR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (06) :454-455

[5]

Green R. D., 1974, HYDROGEN BONDING CH

[6] STRUCTURE OF THE ANTIMALARIAL HALOFANTRINE HYDROCHLORIDE [J].

KARLE, JM ;

KARLE, IL .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 :1248-1250

[7] STRUCTURE OF THIAMINE PICRATE [J].

KIM, MJ ;

SUH, IH ;

AOKI, K ;

YAMAZAKI, H .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1988, 44 :725-727

[8] STRUCTURAL CHARACTERIZATION OF THE MANGANESE(IV) SCHIFF-BASE COMPLEX MNIV (5-CL-SALAHP)2 [J].

LI, XH ;

LAH, MS ;

PECORARO, VL .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 :1517-1519

[9] A PROTOCOL FOR DETERMINING ENANTIOSELECTIVE BINDING OF CHIRAL ANALYTES ON CHIRAL CHROMATOGRAPHIC SURFACES [J].

LIPKOWITZ, KB ;

DEMETER, DA ;

ZEGARRA, R ;

LARTER, R ;

DARDEN, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3446-3452

[10] THIAMINIUM TETRACHLOROCOBALTATE(II) MONOHYDRATE, C12H18N4OS2+.COCL24-.H2O [J].

MACLAURIN, CL ;

RICHARDSON, MF .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1983, 39 (JUL) :854-856