NMR assignment in regioisomeric hydroquinones

Abstract:

A set of regioisomeric pairs of tricyclic hydroquinones, analogues of antitumor 9,10-dihydroxy-4,4-dimethyl-5,8-dihydroanthracen-1(4H)-one (1) and other derivatives, were synthesized and their regiochemistry and NMR spectra assigned by using 1H-detected one-bond (C-H) HMQC and long-range C-H HMBC, in good agreement with theoretical O3LYP/Alhrichs-pVTZ calculations. The 5-hydroxymethyl derivatives (11, 15, 19) showed a 3JH, H coupling constant of methylene protons evidencing the presence of a seven-membered intramolecular hydrogen bonded ring, not observed for the 8-hydroxymethyl isomers. © 2011 John Wiley & Sons, Ltd.

Año de publicación:

2011

Keywords:

• GIAO
• DFT
• O3LYP
• 1 H NMR
• 3 J H H
• Alhrichs-pVTZ
• HMBC
• 13 C NMR
• HMQC
• Hydroquinone

Fuente:

scopus