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Extra info for BarCharts QuickStudy Organic Chemistry Reactions
23). In the 6-NH2 deprotonated radical, an unpaired electron can be delocalized over only three nitrogen atoms. These are single nitrogen of the group NH• and two nitrogens of the six-membered ring. An unpaired electron can also be delocalized over two carbon atoms (one by one of the six- and five-membered rings). 24. Therefore, the N(9) radical should be more stable than the N(6) one. That is why both radicals coexist in the system and both N(9) and N(6) deprotonations take place. In the case of the guanine cation-radical, the presence of the carbonyl group in the pyridazine ring brings about two additional effects: Deprotonation infringes on this ring exclusively, and double deprotonation leads to the formation of a distonic anion-radical.
One-electron reduction of the corresponding metalloporphyrin led to the complex with the porphyrin π anion-radical as a ligand. The nitro group is a strong electron-withdrawing group and its presence obviously lowers the energy level of the ligand-fragmental orbital of the nitro-substituted metallocomplex. Analogously, osmium cluster with the coordinated quinoxaline was designed. The complexes are distinguished by the HOMO based on the metal and by the LUMO based strictly on the ligand. Naturally, such a complex gives rise to the anion-radical in which an unpaired electron spends all its time within the quinoxaline ligand (Nervi et al.
Sasamori et al. (2006a, 2006b) prepared kinetically stable anion-radicals of this type, reducing a parent diaryldiphosphene bearing a bulky substituent in the aryl rings. According to the electrochemical and ESR spectral data alongside the results of DFT calculations, the introduction of one electron leads to the population of the antibonding π* orbital of the P=P double bond with some participation of the aryl moieties. Having this result in mind, it is interesting to scrutinize the role of the C=C bridge in ArCH=CHAr′ derivatives.