A set of regioisomeric pairs of tricyclic hydroquinones, analogues of antitumor 9,10-dihydroxy-4,4-dimethyl-5,8dihydroanthracen- 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-HHMBC, in good agreement with theoretical O3LYP/Alhrichs-pVTZ calculations. The 5-hydroxymethyl derivatives (11, 15, 19) showed a 3 integral 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.
%0 Journal Article
%1 RN34
%A Dobado, J.A.
%A Gomez-Tamayo, J.C.
%A Calvo-Flores, F.G.
%A Martinez-Garcia, H.
%A Cardona, W.
%A Weiss-Lopez, B.
%A Ramirez-Rodriguez, O.
%A Pessoa-Mahana, H.
%A Araya-Maturana, R.
%D 2011
%I 2011 John Wiley & Sons, Ltd.
%J Magnetic Resonance in Chemistry
%K (3)integral alhrichs-pvtz, basis-sets, c-13 calculations, chemical-shifts, coupling-constants, derivatives, dft, diels-alder dqcauchile giao, h,h, h-1 hmbc, hmqc, hydroquinone, nmr, o3lyp, organic-molecules, reaction, respiration, sensitivity, spin theoretical tumor-cell
%N 6
%P 358-365
%R 10.1002/mrc.2745
%T Nmr Assignment in Regioisomeric Hydroquinones
%U /brokenurl#<Go to ISI>://WOS:000291114500009
%V 49
%X A set of regioisomeric pairs of tricyclic hydroquinones, analogues of antitumor 9,10-dihydroxy-4,4-dimethyl-5,8dihydroanthracen- 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-HHMBC, in good agreement with theoretical O3LYP/Alhrichs-pVTZ calculations. The 5-hydroxymethyl derivatives (11, 15, 19) showed a 3 integral 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.
@article{RN34,
abstract = {A set of regioisomeric pairs of tricyclic hydroquinones, analogues of antitumor 9,10-dihydroxy-4,4-dimethyl-5,8dihydroanthracen- 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-HHMBC, in good agreement with theoretical O3LYP/Alhrichs-pVTZ calculations. The 5-hydroxymethyl derivatives (11, 15, 19) showed a 3 integral 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.},
added-at = {2019-12-04T03:57:35.000+0100},
author = {Dobado, J.A. and Gomez-Tamayo, J.C. and Calvo-Flores, F.G. and Martinez-Garcia, H. and Cardona, W. and Weiss-Lopez, B. and Ramirez-Rodriguez, O. and Pessoa-Mahana, H. and Araya-Maturana, R.},
biburl = {https://www.bibsonomy.org/bibtex/2944c28f7728227be48d12cea8f73433d/dqcauchile},
doi = {10.1002/mrc.2745},
interhash = {5059ca9106d23c338109571a4c395bc4},
intrahash = {944c28f7728227be48d12cea8f73433d},
issn = {0749-1581},
journal = {Magnetic Resonance in Chemistry},
keywords = {(3)integral alhrichs-pvtz, basis-sets, c-13 calculations, chemical-shifts, coupling-constants, derivatives, dft, diels-alder dqcauchile giao, h,h, h-1 hmbc, hmqc, hydroquinone, nmr, o3lyp, organic-molecules, reaction, respiration, sensitivity, spin theoretical tumor-cell},
number = 6,
pages = {358-365},
publisher = {2011 John Wiley & Sons, Ltd.},
timestamp = {2019-12-04T03:58:17.000+0100},
title = {Nmr Assignment in Regioisomeric Hydroquinones},
type = {Journal Article},
url = {/brokenurl#<Go to ISI>://WOS:000291114500009},
volume = 49,
year = 2011
}