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

DOI

10.3906/kim-1806-68

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.

Keywords

Hydrogen bonding, 1, 8-naphthalenediol, organocatalysis, phenols

First Page

1398

Last Page

1407

Recommended Citation

TÜRKMEN, YUNUS EMRE (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: Vol. 42: No. 5, Article 17. https://doi.org/10.3906/kim-1806-68
Available at: https://journals.tubitak.gov.tr/chem/vol42/iss5/17