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The interplay of hydrogen bonds and halogen bonds in the structure of NH-pyrazoles bearing C-aryl and C-halogen substituents

AuthorsGarcía, M. A.; Cabildo, Pilar; Claramunt, Rosa M.; Pinilla, Elena; Rosario Torres, M.; Alkorta, Ibon ; Elguero, José
Issue Date2010
CitationInorganica Chimica Acta 363: 1332- 1342 (2010)
AbstractThe behavior in solution and in the solid state of 3(5)-phenyl-1H-pyrazole (7), 3(5)-phenyl-4-chloro-1H-pyrazole (6), 3(5)-phenyl-4-bromo-1H-pyrazole (1), and 3(5)-p-chlorophenyl-4-bromo-1H-pyrazole (8) is discussed in relation to their 3-phenyl (a)/5-phenyl (b) annular tautomerism. Two new X-ray structures are reported: a new polymorph of 1 and the structure of 6. The new polymorph is a 3-phenyl-1H-pyrazole 1a′ trimer while the new structure is a 5-phenyl-1H-pyrazole 6b trimer. The combined use of NMR at low temperature and DFT calculations allows to discuss the tautomerism of the first three pyrazoles and to predict that the fourth one should be a tetramer formed by both tautomers, 8a and 8b. © 2010 Elsevier B.V. All rights reserved.
Publisher version (URL)http://dx.doi.org/10.1016/j.ica.2009.12.059
Identifiersdoi: 10.1016/j.ica.2009.12.059
issn: 0020-1693
Appears in Collections:(IQM) Artículos
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