Investigation of the hydrogen bond donating ability of 1,8-naphthalenediol by NMR spectroscopy and its use as a hydrogen bonding catalyst

Türkmen, Yunus Emre2019-02-212019-02-2120181300-0527http://hdl.handle.net/11693/50446The hydrogen bond donating ability of 1,8-naphthalenediol was investigated via a series of 1H, 13C, and 31P NMR experiments. Complexation studies using triphenylphosphine oxide and cyclohexanone as hydrogen bond acceptors revealed that 1,8-naphthalenediol is a more effective hydrogen bond donor compared to 1-naphthol and 8-methoxy-1-naphthol. Afterwards, its effectiveness as a hydrogen bonding catalyst was demonstrated in the Friedel-Crafts-type addition reaction of indole to trans-β-nitrostyrene.English1,8-NaphthalenediolHydrogen bondingOrganocatalysisPhenolsInvestigation of the hydrogen bond donating ability of 1,8-naphthalenediol by NMR spectroscopy and its use as a hydrogen bonding catalystArticle10.3906/kim-1806-68