title: 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 (1)H-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 (3)J(H, H) coupling constant of methylene protons evidencing the presence of a seven-membered intramolecular hydrogen bonded ring, not observed for the 8-hydroxymethyl isomers.
authors: Grupo de Modelización y Diseño Molecular, Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain. dobado@ugr.es
authors: Jose A
authors: JA
authors: Dobado
authors: José C
authors: JC
authors: Gómez-Tamayo
authors: Francisco G
authors: FG
authors: Calvo-Flores
authors: Henar
authors: H
authors: Martínez-García
authors: Wilson
authors: W
authors: Cardona
authors: Boris
authors: B
authors: Weiss-López
authors: Oney
authors: O
authors: Ramírez-Rodríguez
authors: Hernán
authors: H
authors: Pessoa-Mahana
authors: Ramiro
authors: R
authors: Araya-Maturana
mesh_terms: D006860:Hydrogen Bonding; D006873:Hydroquinones / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000592:standards; D015394:Molecular Structure; D011789:Quantum Theory; D012015:Reference Standards; D013237:Stereoisomerism
chemical_list: D006873:Hydroquinones