Melting point–solubility–structure correlations in chiral and racemic model cocrystals,CrystEngComm

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Melting point–solubility–structure correlations in chiral and racemic model cocrystals
CrystEngComm ( IF 2.6 ) Pub Date : 2020-03-27 , DOI: 10.1039/d0ce00014k
Ornella E. Y. Kilinkissa _{1,

2,

3,

4} , Krishna K. Govender _{4,

5,

6,

7,

8} , Nikoletta B. Báthori _{1,

2,

3,

4}

Affiliation

The impact of chirality is assessed via comparison of structural features and properties of binary cocrystals. 4,4′-Bipyridine and 1,2-bis(4-pyridyl)ethane were combined with achiral, racemic mixture or pure enantiomers of selected carboxylic acids with similar constituents (p-toluic acid, rac-2-phenylbutyric acid, racemic or S-phenylsuccinic acid). Single crystal structures, thermal analysis, powder X-ray analysis and equilibrium solubility in water and ethanol of the cocrystals were measured. It was concluded that the aqueous solubility of the cocrystals is inversely related to their melting points and this trend can be linked to some packing features. It was shown that the introduction of a chiral building block limits the formation of certain intermolecular interactions in the chiral multicomponent crystals and thus decreases the efficiency of the packing, which eventually leads to lower melting points and higher aqueous solubility.

中文翻译：

手性和外消旋模型共晶体的熔点-溶解度-结构相关

通过比较二元共晶体的结构特征和性质来评估手性的影响。将4,4'-联吡啶和1,2-双（4-吡啶基）乙烷与具有相似成分的选定羧酸的非手性，外消旋混合物或纯对映异构体（对甲苯甲酸，rac -2-苯基丁酸，外消旋或小号-苯基琥珀酸）。测量了共晶体的单晶结构，热分析，粉末X射线分析以及在水和乙醇中的平衡溶解度。结论是，共晶体的水溶性与它们的熔点成反比，并且这种趋势可以与某些堆积特征有关。结果表明，手性结构单元的引入限制了手性多组分晶体中某些分子间相互作用的形成，从而降低了填充效率，最终导致较低的熔点和较高的水溶性。

更新日期：2020-03-27

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