The ¹HNMR spectra of all possible structural isomers of mono and dihydroxy substituted naphthalenes are measured in trifluoracetic acid and trifluormethanesulfonic acid as well as in their deuterated derivatives. These spectra indicate different protonation/deuteration positions in the compounds studied. Whereas with the relative weak TFA the OH group as most basic group of the substrates is protonated, with the more acidic TFS also aromatic positions with lower basicity are protonated. However, some of these position were indicated only by using deutertated acids. To quantify the degree of proton/deuterium exchange at the aromatic rings, dioxane as proton standard was used. For the OH-protonation a complex between the appropriate naphthol and the acid used, in which a quick proton exchange can be occur, is assumed. Furthermore, the formation of corresponding trifluoroacetates or triflates by reaction of the naphthols with the corresponding acids has been indicated. In some cases, in which the ring positions of protonation are not definitely clear, 2D NOESYNMR experiments have been performed.
| Identifer | oai:union.ndltd.org:DRESDEN/oai:qucosa:de:qucosa:90717 |
| Date | 16 May 2024 |
| Creators | Hartmann, Horst, Yu, Xiuling |
| Publisher | Wiley-VCH |
| Source Sets | Hochschulschriftenserver (HSSS) der SLUB Dresden |
| Language | English |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, doc-type:article, info:eu-repo/semantics/article, doc-type:Text |
| Rights | info:eu-repo/semantics/openAccess |
| Relation | 2365-6549, e202202836, 10.1002/slct.202202836 |
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