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The hydrogen bond donating ability of 1,8-naphthalenediol was investigated via a series of 1 " role="presentation"> 1 1 ^{1} H, 13 " role="presentation"> 13 13 ^{13} C, and 31 " role="presentation"> 31 31 ^{31} P 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 " role="presentation"> β β \beta -nitrostyrene.

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