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, cilt.42, sa.5, ss.1398-1407, 2018 (SCI-Expanded, Scopus, TRDizin)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 42 Sayı: 5
- Basım Tarihi: 2018
- Doi Numarası: 10.3906/kim-1806-68
- Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
- Sayfa Sayıları: ss.1398-1407
- Orta Doğu Teknik Üniversitesi Adresli: Hayır
Özet
The hydrogen bond donating ability of 1,8-naphthalenediol was investigated via a series of H-1, C-13, and P-31 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.