Turkish Journal of Chemistry
Abstract
The hydrogen bond donating ability of 1,8-naphthalenediol was investigated via a series of $^{1}$H, $^{13}$C, and $^{31}$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-$\beta $-nitrostyrene.
DOI
10.3906/kim-1806-68
Keywords
Hydrogen bonding, 1, 8-naphthalenediol, organocatalysis, phenols
First Page
1398
Last Page
1407
Recommended Citation
TÜRKMEN, Y. E (2018). Investigation of the hydrogen bond donating ability of 1,8-naphthalenediol by NMR spectroscopy and its use as a hydrogen bonding catalyst. Turkish Journal of Chemistry 42 (5): 1398-1407. https://doi.org/10.3906/kim-1806-68
