✦ LIBER ✦
A density functional theoretical study of the influence of cavities and water molecules on tautomerism: The case of pyridones and 1,2,4-triazoles linked to crown ethers and esters
✍ Scribed by Ibon Alkorta; José Elguero
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2001
- Tongue
- English
- Weight
- 82 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
The tautomerism of pyridones and 1,2,4‐triazoles related to two crown ethers and two crown esters derived from these heterocycles was studied theoretically. For the four macrocycles, Bradshaw identified a single tautomer by X‐ray crystallography. To rationalize these findings, a series of calculations from simple models to crown derivatives have been carried out. The most interesting case concerns the observation, for the first time, of a 4H‐1,2,4‐triazole tautomer. To explain this result it was necessary to calculate the whole crown ester plus a caged water molecule was necessary.