Co-crystals of caffeine and hydroxy-2-naphthoic acids: Unusual formation of the carboxylic acid dimer in the presence of a heterosynthon

被引：91

作者：

Bucar, Dejan-Kresimir

Henry, Rodger F.

Lou, Xiaochun

Duerst, Richard W.

Borchardt, Thomas B.

MacGillivray, Leonard R.

Zhang, Geoff G. Z.

机构：

[1] Abbott Labs, Global Pharmaceut R&D, Solid State Sci, N Chicago, IL 60064 USA

[2] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA

[3] Abbott Labs, Global Pharmaceut R&D, Struct chem, Abbott Pk, IL 60064 USA

[4] Abbott Labs, Global Pharmaceut R&D, Microscopy Grp, Abbott Pk, IL 60064 USA

[5] Abbott Labs, Global Pharmaceut R&D, Solid State Chem, N Chicago, IL 60064 USA

来源：

MOLECULAR PHARMACEUTICS | 2007年 / 4卷 / 03期

关键词：

pharmaceutical co-crystals; co-crystal screening; hydrogen bond; caffeine; naphthoic acid; supramolecular synthon; crystal engineering; 1-hydroxy-2-naphthoic acid; 3-hydroxy-2-naphthoic acid; 6-hydroxy-2-naphthoic acid;

D O I：

10.1021/mp070004b

中图分类号：

R-3 [医学研究方法]; R3 [基础医学];

学科分类号：

1001 ;

摘要：

A group of caffeine-containing co-crystals of hydroxy-2-naphthoic acids were synthesized and analyzed via single-crystal X-ray diffraction and IR analysis. The imidazole-carboxylic acid synthon was observed in co-crystals involving 1-hydroxy-2-naphthoic and 3-hydroxy-2-naphthoic acid. In the case of 6-hydroxy-2-naphthoic acid, the co-crystal exhibits a hydrogen-bonded carboxylic acid dimer in the presence of a hydroxyl-caffeine heterosynthon.

引用

页码：339 / 346

页数：8

共 58 条

[1] Is conformational flexibility in a supramolecular reagent advantageous for high-yielding co-crystallization reactions? [J].