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Substituent effects on the basicity (p: K a) of aryl guanidines and 2-(arylimino)imidazolidines: Correlations of pH-metric and UV-metric values with predictions from gas-phase ab initio bond lengths

AutorDardonville, Christophe ; Caine, B. A.; Navarro de la Fuente, Marta; Martín Herranz, Guillermo; Corrales Mariblanca, Beatriz; Popelier, Paul L. A.
Fecha de publicación2017
EditorRoyal Society of Chemistry (Great Britain)
CitaciónNew Journal of Chemistry 41: 11016-11028 (2017)
ResumenThe dissociation constants of two related series of 2-(arylimino)imidazolidine and aryl guanidine α-adrenoceptor antagonists (35 compounds in total) were measured by potentiometric titrations and by UV-spectrophotometry using the 96-well microtitre plate method. The experimental values obtained using both methods were quite consistent and showed a very good agreement with the pK values calculated using the AIBLHiCoS methodology, which uses only a single bond length obtained using ab initio calculations at a low level of theory. The prediction power of the imidazolidine and guanidine set of compounds was very good with deviations typically <0.30 and <0.24 pK units, and a mean absolute error (MAE) of 0.23 and 0.29, respectively. The study of the quantitative effect of diverse substituents on the basicity of aryl guanidine and 2-(arylimino)imidazolidine derivatives is useful for medicinal chemists working with biologically relevant guanidine-containing molecules.
Versión del editorhttp://dx.doi.org/10.1039/c7nj02497e
URIhttp://hdl.handle.net/10261/157440
DOI10.1039/c7nj02497e
Identificadoresdoi: 10.1039/c7nj02497e
issn: 1144-0546
e-issn: 1369-9261
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