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A molecular balance to measure the strength of N-H⋯π hydrogen bonds based on the tautomeric equilibria of C-benzylphenyl substituted NH-pyrazoles

AuthorsCornago, Pilar; Claramunt, Rosa M.; Bouissane, L.; Elguero, José
Issue Date2008
PublisherPergamon Press
CitationTetrahedron 64: 3667- 3673 (2008)
AbstractA theoretical (B3LYP/6-31G**) study of 30 pyrazoles, most of them existing in two tautomeric forms, has been carried out. 3(5)-(2-Benzylphenyl)-5(3)-methyl-1H-pyrazole (11) and 3(5)-(2-benzylbenzylphenyl)-5(3)-phenyl-1H-pyrazole (20) were synthesized from 2-benzoylacetophenone, and their annular tautomeric equilibrium determined. The substituent effects were statistically analyzed and discussed with the help of Hammett substituent constants. In the case of the 5-(2-benzylphenyl) groups, the strength of the N-H⋯π hydrogen bond depends on the electronic effect of the substituent at position 3. © 2008 Elsevier Ltd. All rights reserved.
Publisher version (URL)http://dx.doi.org/10.1016/j.tet.2008.02.026
Identifiersdoi: 10.1016/j.tet.2008.02.026
issn: 0040-4020
Appears in Collections:(IQM) Artículos
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