| Autor: |
Rajesh G. Gonnade, Shobhana Krishnaswamy, Mysore S. Shashidhar, Majid I. Tamboli |
| Rok vydání: |
2013 |
| Předmět: |
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| Zdroj: |
Chemistry - A European Journal. 19:12867-12874 |
| ISSN: |
0947-6539 |
| DOI: |
10.1002/chem.201301058 |
| Popis: |
Investigation of the intermolecular acyl-transfer reactivity in molecular crystals of myo-inositol orthoester derivatives and its correlation with crystal structures enabled us to identify the essential parameters to support efficient acyl-transfer reactions in crystals: 1) the favorable geometry of the nucleophile (-OH) and the electrophile (C-O) and 2) the molecular assembly, reinforced by C-H⋅⋅⋅π interactions, which supports a domino-type reaction in crystals. These parameters were used to identify another reactive crystal through a data-mining study of the Cambridge Structural Database. A 2:1 co-crystal of 2,3-naphthalene diol and its di-p-methylbenzoate was selected as a potentially reactive crystal and its reactivity was tested by heating the co-crystals in the presence of solid sodium carbonate. A facile intermolecular p-toluoyl group transfer was observed as predicted. The successful identification of reactive crystals opens up a new method for the detection of molecular crystals capable of exhibiting acyl-transfer reactivity. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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