- Turkish Journal of Chemistry
- Vol: 42 Issue: 5
- Investigation of the hydrogen bond donating ability of 1,8-naphthalenediol by NMR spectroscopy and i...
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
View : 8 | Download : 3
Publication Date : 9999-12-31
Article Type : Makaleler
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