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

Authors : Yunus Emre TÜRKMEN

Pages : 1398-1407

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Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :  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.
Keywords : Hydrogen bonding, 1, 8 naphthalenediol, organocatalysis, phenols