2009
DOI: 10.1016/j.jfluchem.2009.05.004
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C–F⋯HO hydrogen bond in 8-fluoro-4-methyl-1-naphthol

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Cited by 30 publications
(24 citation statements)
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“…Alkorta et al have reported that calculated F,H(N) spin–spin couplings across the hydrogen bond in 2‐fluorobenzamide and related compounds vary from ca 11 to 15 Hz, which are also significantly high, even considering that primary amides are much less acidic (pKa ≈ 17) than 2‐hydroxy‐2‐cyclohexenona (pKa = 10.3). The calculated 1h J F,H(O) for 3 of ca –30 Hz does not appear to be overestimated when considering a F···HO hydrogen bonded system; for instance, in 8‐fluoro‐4‐methyl‐1‐naphthol, the experimental 1h J F,H(O) coupling constant is (−)28.4 Hz . Thus, the 1h J F,H(O) coupling constant can yield information that is fundamental to understanding the role of hydrogen bond in biological systems.…”
Section: Resultsmentioning
confidence: 99%
“…Alkorta et al have reported that calculated F,H(N) spin–spin couplings across the hydrogen bond in 2‐fluorobenzamide and related compounds vary from ca 11 to 15 Hz, which are also significantly high, even considering that primary amides are much less acidic (pKa ≈ 17) than 2‐hydroxy‐2‐cyclohexenona (pKa = 10.3). The calculated 1h J F,H(O) for 3 of ca –30 Hz does not appear to be overestimated when considering a F···HO hydrogen bonded system; for instance, in 8‐fluoro‐4‐methyl‐1‐naphthol, the experimental 1h J F,H(O) coupling constant is (−)28.4 Hz . Thus, the 1h J F,H(O) coupling constant can yield information that is fundamental to understanding the role of hydrogen bond in biological systems.…”
Section: Resultsmentioning
confidence: 99%
“…NMR analysisf ocusedo nt he multiplicity, h1 J OH···F value,a nd chemicals hift of the alcohol protonsa t2 5 8Ca nd À50 8C, taking into account that the observed values are averaged over the conformer populations.T he results are given in Ta 12 ]cyclohexane. [17,18] With an exceptionally resolved NMR spectrum (Figure 3), we have succeeded to detect an OH signal clearly appearing as at riplet of doublets in CDCl 3 ,a nd the 1 H{ 19 F} analysis proved that there is a1 .4 Hz coupling to fluorine.…”
Section: Nmr Experiments Revealo H···f Coupling Constants For All Invmentioning
confidence: 99%
“…After the debate about the effective ability of fluorine to act as a hydrogen-bond (H-bond, HB) acceptor, [11][12][13][14][15] the occurrence of intermolecular OHF H-bonding is now clearly established through experimental and theoretical evidences. [16][17][18][19][20] The existence of intramolecular hydrogen bonds (IMHBs) involving fluorine has also been scrutinised and highlighted experimentally through NMR techniques for conformationally constrained, [21][22][23] partially flexible, 24 and even fully flexible fluorohydrins. 25 We have recently reported that the intermolecular hydroxyl H-bond donating capacity (or HB acidity) in conformationally fixed fluorohydrins (eg 1, Figure 1) 21 and partially flexible benzyl alcohols (eg 2) 26 is deeply influenced by the conformational preferences dictated by the presence of such IMHBs.…”
Section: Introductionmentioning
confidence: 99%