Summary
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1.
The equilibrium NH acidities of benzenesulfonamide and its derivatives have been studied by the transmetallation method in DMSO.
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2.
Linear relationships connecting the pK values of benzenesulfonamides C6H5SO2NHR with the σ* constants of alkyl groups R and of substituted benzenesulfonanilides C6H5SO2NHC6H4R′ with the σ constants of the substituents R′ have been found. The acidifying effect of the phenylsulfonyl group on its introduction into aniline and into 4-aminopyridine has been evaluated.
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3.
A linear relationship has been established between the pK values of anilines and 4-anilinopyridines substituted in the amino groups, and on this basis the presumed pK values of a number of aminopyridine derivatives in DMSO have been calculated.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1259–1264, June, 1981.
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Kravtsov, D.N., Peregudov, A.S., Petrov, É.S. et al. Equilibrium nh acidity of benzenesulfonamide and its derivatives in dimethyl sulfoxide. Russ Chem Bull 30, 993–997 (1981). https://doi.org/10.1007/BF00950279
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DOI: https://doi.org/10.1007/BF00950279