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Beilstein J. Org. Chem. 2011, 7, 320–328, doi:10.3762/bjoc.7.42
Graphical Abstract
Figure 1: 1,8-disubstituted naphthalene model systems.
Scheme 1: The general reaction for the preparation of the 1,8-disubstituted naphthol derivatives 1–5 [31].
Figure 2: X-ray structure of 8-(4-methylphenyl)-1-naphthol derivative 4.
Figure 3: Potentiometric titration data for compound 1 and TBAH.
Figure 4: Structures (a) with the hydrogen atom pointing into the ring, as seen in the crystal structure of 4...
Scheme 2: Titration of the acids 1–5 to generate the corresponding anions 8–12, respectively.
Figure 5: Plot of pKa' values for compounds 1–5 versus the corresponding R-substituent σp Hammett parameter. ...
Figure 6: Anion density (HOMO) for the phenyl-derivative 8, illustrating no conjugation of the anion with the...
Figure 7: Bond critical points (red), ring critical points (yellow) and bond paths illustrated for the anion 8...