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4
-
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0342830707
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note
-
The standard nomenclature of tautomeric 4(7)-substituted benzimidazoles (and their related N-alkyl) systems, as exemplified by 4-methyl-1H-benzimidazole ⇆ 7-methyl-1H-benzimidazole is awkward to use when describing competitive nitrogen alkylation reactions. Rather than using the pyrrolic nitrogen (>N-R) as the numeric origin, we give the benzenoid ring substituent a fixed (lower) number and use this to assign the N1 and N3 sites (see Fig. 1); this leads to a more convenient description of the isomeric products.
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14
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0342830699
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-
note
-
The selectivity factor is the differential free energy for reaction at the competitive N1-and N3-sites of the benzimidazole anion under consideration, s = ΔΔG‡ = -RT ln(N1% / N3%) kJ/mol.
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