ArticleBeilstein journal of organic chemistry2011
Anion-π interactions influence pK(a) values.
Article in Beilstein journal of organic chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
2 citing papers in PubMed, 12 citations in OpenAlex.
- Ruthenium-Catalyzed C-H Arylation of 1-Naphthol with Aryl and Heteroaryl Halides.The Journal of organic chemistry · 2019Article
- Modulation of Phenol Oxidation in Cofacial Dyads.Journal of the American Chemical Society · 2015Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
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Abstract
Five 8-(4-R-phenyl)-1-naphthol derivatives were prepared by PdCl(2)-catalysed electrophilic aromatic substitution. The pK(a)' values for these 1,8-disubstituted arene naphthols have been measured in acetonitrile/water (R = NO(2), 8.42; R = Cl, 8.52; R = H, 8.56; R = Me 8.68; and R = OMe, 8.71) and indicate a correlation with the electronic nature of the arene substituent, as determined through LFER analysis. Contributions to the relative pK(a)' values have been interpreted, using M06-2X DFT calculations, as consisting of two components: A small contribution from initial OH-π bonding in the starting materials and a larger contribution from anion-π interactions in the products. Such effects have implications for a range of other systems.
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