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A multinuclear magnetic resonance study of fluoro derivatives of hydroxybenzaldehydes
Author(s) -
Sanz Dionisia,
Nieto Carla,
Claramunt Rosa M.,
Alkorta Ibon,
Elguero José
Publication year - 2015
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.4260
Subject(s) - chemistry
The characterization of hydroxybenzaldehydes bearing one or\udtwo fluorine substituents presents some problems that were\udsolved by the use of traditional NMR experiments assisted by\udtheoretical calculations. The present work concerns the following\udsix derivatives (Fig. 1): 4-fluoro-3-methoxybenzaldehyde\ud(1), mp 58.7–59.6 °C; 2-fluoro-4-hydroxybenzaldehyde (2),\udmp 170–173 °C; 3-fluoro-4-hydroxybenzaldehyde (3), mp 126–\ud126.5 °C; 2,3-difluoro-4-hydroxybenzaldehyde (4), mp 141–142 °C;\ud2,5-difluoro-4-hydroxy-benzaldehyde (5), mp 146.1–146.3 °C; and\ud2,4-difluoro-3-hydroxybenzaldehyde (6), mp 141.3–141.7 °C. Note\udthat compounds 4 and 6 have the samemelting point. The spectroscopic\udinformation about these compounds is scarce, only about 6\udhas been published a paper where 1H and 19F NMR data were\udreported.[1] In particular, the high value of 4JFF in compound 6 shed\uddoubts about its structure.This work has been supported by the Spanish Ministerio de Ciencia\ude Innovación (CTQ2010-16122), the Ministerio de Economía y\udCompetitividad (CTQ2012-35513-C02-02, CTQ2014-56833-R),\udand the Comunidad Autónoma de Madrid (S2013/MIT-2841,\udFotocarbon). Computer, storage, and other resources from\udthe CTI (CSIC) are gratefully acknowledged. One of us (C.\udI. Nieto) is indebted to UNED for a predoctoral fellowship\ud(FPI ‘Grupos de Investigación’ UNED).Peer Reviewe