CHED 855 |
| Evan W. Miller, Faith E. Jacobsen, and Victor Heasley. Department of Chemistry, Point Loma Nazarene University, 3900 Lomaland Drive, San Diego, CA 92106 |
| The reaction of dilute 2,4,6-trichlorophenol with excess mono- and dichloramine in aqueous conditions results in the replacement of the para- chlorine and the formation of the corresponding N-chloro-immine. Although the formation of 2,6-dichloro-1,4-benzoquinone-4-(N-chloro) imine has been reported previously, no mechanism has been proposed. Ammonia, a stronger base than either mono- or dichloramine, did not form the imine. This eliminates the possibility of a direct, nucleophilic attack by nitrogen. Studies involving the formation of indophenols suggest an ion-radical mechanism that allows for the displacement of para- substituted chlorine by nitrogen. Our studies show experimental similarities to indopenol formation. We discuss the reactions and mechanism in order to propose that the displacement of para- substituted chlorine by nitrogen proceeds by an ion-radical mechanism. |
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Undergraduate Research Poster Session: Organic Chemistry
2:00 PM-4:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Chemical Education |