Isolation, structure, and properties of quinone-aci
tautomer of a phenol-nitro compound related to
eugenoxyacetic acid
Dinh N.H., Huan T.T., Toan D.N., Kimpende P.M., Meervelt L.V.
Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy Hanoi, Viet Nam;
Chemistry Department K.U. Leuven, Biomolecular Architecture, Celestijnenlaan 200F, B-3001 Leuven,
Belgium
Abstract: Treatment with excess nitric acid in acetic acid revealed that eugenoxyacetic acid underwent an
unexpected ether cleavage, a normal nitration, and then an unexpected electrophilic addition to the double
bond of the side chain that led to the formation of a dinitro compound which subsequently converted to a
sensitive, reactive quinone-aci compound. The structure of the quinone-aci compound (1) and its derivatives
(2-6) was established by 1D- , 2D NMR, MS spectra, and chemical methods. In addition, the XRD structure
of compound 2 derived from 1 was established. A double tautomerization of 1 in solution was studied by the
LC-UV-MS method. © 2010 Elsevier B.V. All rights reserved.
Author Keywords: Eugenoxyacetic acid; Nitro-aci tautomerization; Nitrophenol; Quinone; Tautomer
Index Keywords: Eugenoxyacetic acid; Nitrophenols; Quinone; Tautomer; Tautomerizations; Chemical
bonds; Ethers; Nitric acid; Phenols; Acids
Year: 2010
Source title: Journal of Molecular Structure
Volume: 980
Issue: 3-Jan
Page : 137-142
Link: Scorpus Link
Correspondence Address: Dinh, N. H.; Department of Chemistry, Hanoi National University of Education,
136 Xuan Thuy Hanoi, Viet Nam; email: [email protected]
ISSN: 222860
CODEN: JMOSB
DOI: 10.1016/j.molstruc.2010.07.005
Language of Original Document: English
Abbreviated Source Title: Journal of Molecular Structure
Document Type: Article
Source: Scopus
Authors with affiliations:
1. Dinh, N.H., Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy Hanoi, Viet Nam
2. Huan, T.T., Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy Hanoi, Viet Nam
3. Toan, D.N., Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy Hanoi, Viet Nam
4. Kimpende, P.M., Chemistry Department K.U. Leuven, Biomolecular Architecture, Celestijnenlaan 200F, B-3001 Leuven,
Belgium
5. Meervelt, L.V., Chemistry Department K.U. Leuven, Biomolecular Architecture, Celestijnenlaan 200F, B-3001 Leuven,
Belgium
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