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A multinuclear magnetic resonance study of fluoro derivatives of hydroxybenzaldehydes

AuthorsSanz, Dionisia; Nieto, Carla; Claramunt, Rosa M.; Alkorta, Ibon ; Elguero, José
Issue Date2015
PublisherJohn Wiley & Sons
CitationMagnetic Resonance in Chemistry 53: 624-631 (2015)
AbstractThe characterization of hydroxybenzaldehydes bearing one or two fluorine substituents presents some problems that were solved by the use of traditional NMR experiments assisted by theoretical calculations. The present work concerns the following six derivatives (Fig. 1): 4-fluoro-3-methoxybenzaldehyde (1), mp 58.7–59.6 °C; 2-fluoro-4-hydroxybenzaldehyde (2), mp 170–173 °C; 3-fluoro-4-hydroxybenzaldehyde (3), mp 126– 126.5 °C; 2,3-difluoro-4-hydroxybenzaldehyde (4), mp 141–142 °C; 2,5-difluoro-4-hydroxy-benzaldehyde (5), mp 146.1–146.3 °C; and 2,4-difluoro-3-hydroxybenzaldehyde (6), mp 141.3–141.7 °C. Note that compounds 4 and 6 have the samemelting point. The spectroscopic information about these compounds is scarce, only about 6 has been published a paper where 1H and 19F NMR data were reported.[1] In particular, the high value of 4JFF in compound 6 shed doubts about its structure.
Publisher version (URL)http://dx.doi.org/10.1002/mrc.4260
Identifiersdoi: 10.1002/mrc.4260
issn: 0749-1581
e-issn: 1097-458X
Appears in Collections:(IQM) Artículos
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