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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
Author(s) -
Alkorta Ibon,
Elguero José
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380622
Subject(s) - tautomer , chemistry , crown (dentistry) , molecule , computational chemistry , triazole , 2 pyridone , 18 crown 6 , stereochemistry , organic chemistry , medicine , dentistry
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.