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首页> 外文期刊>Crystal growth & design >Cocrystallization of 2,3-Dihydroxynaphthalene with Its para-, meta-, and ortho-Ditoluates: Insight into Cocrystal Formation and Clues for the Construction of Supramolecular Assemblies Capable of Intermolecular Acyl Group Transfer Reactivity
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Cocrystallization of 2,3-Dihydroxynaphthalene with Its para-, meta-, and ortho-Ditoluates: Insight into Cocrystal Formation and Clues for the Construction of Supramolecular Assemblies Capable of Intermolecular Acyl Group Transfer Reactivity

机译：2,3-二羟基萘及其对位，间位和邻位Ditoluates的共结晶：洞察共晶体形成和线索的能力分子间酰基转移活性的超分子组装的建设。

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2,3-Dihydroxynaphthalene forms 2:1 cocrystals with its p-ditoluate and 1:1 cocrystals with its m-ditoluate but not with the o-ditoluate. In 2:1 cocrystals of the p-ditoluate, naphthalene diol molecules form a dimeric motif through OH...O hydrogen bonding interactions. The adjacent dimers sandwich the molecules of p-ditoluate through C-H...pi interactions. In 1:1 cocrystals of the m-ditoluate, naphthalene diol molecules generate a zigzag pattern through O-H...O hydrogen bonding interaction involving -OH of the diol and the C=O of the m-ditoluate. Intermolecular toluoyl group transfer reaction was more facile in cocrystals of the p-ditoluate as compared to cocrystals of the m-ditoluate. This difference in reactivity is consistent with the relative geometry of the electrophile (El, C-O) and the nucleophile (Nu, OH) in these cocrystals. A comparison of the cocrystallization behavior and structure of the two cocrystals with their constituents suggests that the position of the methyl group is crucial for cocrystal formation. A survey of the CSD revealed that the incidence of polymorphism and cocrystals formation decreases (number of hits) in the order para- > ortho- > meta- for disubstituted benzene derivatives. This suggests that compounds prone to exhibit polymorphism have more propensities to form cocrystals as compared to those that resist polymorphism. This information could be useful while selecting cocrystal formers and construction of supramolecular functional assemblies with desired properties.
机译：2,3-二羟基萘与其对-乙醇酸酯形成2：1共晶体，与间-乙醇酸酯形成1：1共晶体，而不与邻-乙醇酸酯形成。在对苯二甲酸的2：1共晶体中，萘二醇分子通过OH ... O氢键相互作用形成二聚基序。相邻的二聚体通过C-H ... pi相互作用将对羟基苯二酸酯分子夹在中间。在间苯二酸酯的1：1共晶体中，萘二醇分子通过涉及二醇的-OH和间苯二酸酯的C = O的O-H ... O氢键相互作用产生锯齿形。与间苯二酸酯的共晶体相比，对甲苯二酸酯的共晶体的分子间甲苯酰基基团转移反应更容易。反应性的这种差异与这些共晶体中亲电试剂（E1，C-O）和亲核试剂（Nu，OH）的相对几何形状一致。比较两种共晶的共结晶行为和结构及其成分表明，甲基的位置对于共晶的形成至关重要。对CSD的一项调查显示，对于二取代苯衍生物，多态性和共晶形成的发生率以对->邻->间-的顺序降低（命中数）。这表明与具有抗多态性的化合物相比，易于表现出多态性的化合物具有更大的共晶形成倾向。该信息在选择共晶形成物和具有所需特性的超分子功能组装体时可能会有用。

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