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
| Autor: | Majid I. Tamboli, Mysore S. Shashidhar, Rajesh G. Gonnade, Vir Bahadur |
|---|---|
| Rok vydání: | 2015 |
| Předmět: | |
| Zdroj: | Crystal Growth & Design. 15:1226-1232 |
| ISSN: | 1528-7505 1528-7483 |
| DOI: | 10.1021/cg501620g |
| Popis: | 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 O–H···O hydrogen bonding interactions. The adjacent dimers sandwich the molecules of p-ditoluate through C–H···π 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 cocrys... |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|