ANYL 49 |
| A large number of synthetic and natural organic compounds containing a quinone moiety in their structure have been associated with different biological activities. Many of these compounds have been used as antitumor agents, antibacterial agents, antimicrobial agents, antimalarial agents, herbicides and fungicides. In most cases, the biological activity of quinones has been related to their redox properties and their capacity to accept one or two electrons to form the corresponding radical-anion and hydroquinone radical dianion. The electron-accepting capacity of a given quinone can be modified by directly adding a substituted aniline to the quinone system. In this type of compounds, the attracting and donor properties of the substituents modify their redox properties either facilitating or interfering with the charge transfer from the substituent to the quinone. In this paper, the effect of different fluoro-substituents on the structure and redox properties of 2-(phenylamine)-1,4-naphthoquinone has been investigated. Since fluorine atoms are known to form hydrogen bonds and present both, electron atracting and donor properties, the presence of one or more fluorine atoms on aniline, attached to the quinone structure, must have some interesting effects on the physicochemical properties of this molecule. All the compounds prepared were characterized by X-Ray crystallography, IR, UV-Vis, 1HNMR, mass spectrometry and cyclic voltammetry. |
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General Papers
7:00 PM-9:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster
Division of Analytical Chemistry |