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13
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0011888315
-
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note
-
The symmetry of both ions places their centers of charge along the central axis of the ions. The center of charge of 1 is estimated to lie ∼0.2 Δ above the pyridinium nitrogen (still in the plane of the ring) due to delocalization of the charge within the pyridinium ring. The center of charge of 2 is estimated to lie directly between the carboxylate oxygens, ∼0.7 Δ above the carboxylate carbon.
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-
-
-
14
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84990665975
-
-
For an example of such cooperative reactivity between the charged and radical moieties see: Stirk, K. M.; Smith, R. L.; Orlowski, J. C.; Kenttämaa, H. I. Rapid Comm. Mass Spectrom. 1993, 7, 392-399.
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0011901333
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Vertical values calculated at the B3LYP/6-31+G(d) level of theory. These vertical values are shown to be more applicable than adiabatic values to the estimation of polar effects.
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0011909463
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note
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Note that this IE of the phenyl radical moiety does not correspond to removal of an electron from the HOMO of the 3-dehydrobenzoate anion to form a biradical rather than the desired zwitterionic neutralized form. Instead, the 6.0 eV IE reflects the removal of an electron from the lower energy orbital that most closely corresponds to the SOMO of the phenyl radical.
-
-
-
-
47
-
-
0011821403
-
-
note
-
Note that this negative EA value corresponds to an ion that is unbound with respect to spontaneous electron detachment. For the purposes of polar effects, it merely serves to indicate and extreme disinclination by 2 for any electrophilic radical reactivity.
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48
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