Construction of Two-Component Chemically Reactive Supramolecular Assemblies-Acyl Migration Reactions in Cocrystals of Napthalene-2,3-Diol and Its Diesters,ChemPlusChem

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Construction of Two-Component Chemically Reactive Supramolecular Assemblies-Acyl Migration Reactions in Cocrystals of Napthalene-2,3-Diol and Its Diesters
ChemPlusChem ( IF 3.0 ) Pub Date : 2021-07-26 , DOI: 10.1002/cplu.202100139
Vir Bahadur _{1,

2} , Rajesh G Gonnade _{2,

3} , Majid I Tamboli ₁ , Shobhana Krishnaswamy ₃ , Mysore S Shashidhar _{1,

2}

Affiliation

Reactions in solids are of contemporary interest due to applications in pharmaceutical industries to environmental sustainability. Although several reactive crystals that support chemical reactions have been identified and characterized, the same cannot be said about reactive cocrystals. Earlier we correlated the facile acyl group transfer reactions in crystals with supramolecular parameters obtained from the crystal structures. The structure-reactivity correlation revealed the requirement of proper juxtaposition of electrophile (C=O) and the nucleophile (OH) with distance (∼3.2 Å) and angle (∼90°) along the chain structure. The current article describes the preparation of cocrystals that are capable of supporting intermolecular acyl group transfer reactions in a group of structurally similar molecules. The cocrystals of naphthalene 2,3-diol and its corresponding diesters showed a facile solid state acyl transfer reaction, which has been well correlated with their crystal structures.

中文翻译：

双组分化学反应性超分子组装体的构建-2,3-萘二醇及其二酯共晶中的酰基迁移反应

由于在制药工业中对环境可持续性的应用，固体中的反应引起了当代的兴趣。尽管已经鉴定和表征了几种支持化学反应的反应晶体，但对于反应共晶体却不能说同样的情况。早些时候，我们将晶体中容易发生的酰基转移反应与从晶体结构获得的超分子参数相关联。结构-反应性相关性揭示了亲电子试剂 (C=O) 和亲核试剂 (OH) 沿着链结构以距离 (∼3.2 Å) 和角度 (∼90°) 适当并置的要求。本文描述了能够支持一组结构相似的分子中的分子间酰基转移反应的共晶体的制备。萘2,3-二醇及其相应二酯的共晶表现出容易的固态酰基转移反应，这与其晶体结构有很好的相关性。

更新日期：2021-08-17

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