Deprotonation mechanism of new antihypertensive piperidinylmethylphenols: a combined experimental and theoretical study.
Four new antihypertensive piperidinylmethylphenol compounds were synthesized for their potential antihypertensive and antiarhythmic properties. The pKa values were determined experimentally, with the aid of the program SQUAD, by capillary zone electrophoresis (CZE) at T=298.15 K and 0.015 M ionic strength (I=0.05 M) and by UV spectrophotometry at pseudophysiological conditions (T=310.15 K and I=0.15 M), obtaining good agreement between the values determined with both techniques. A theoretical study was followed in order to propose a deprotonation mechanism for each compound.
Islas-Martínez
José Manuel
JM
Departamento de Química, Area de Química Analítica, Universidad Autónoma Metropolitana-Iztapalapa, Ap. Postal 55-534, San Rafael Atlixco 186. Col. Vicentina, 09340 México, D.F. Mexico.
Rodríguez-Barrientos
Damaris
D
Galano
Annia
A
Angeles
Enrique
E
Torres
Luis A
LA
Olvera
Fabiola
F
Ramírez-Silva
María Teresa
MT
Rojas-Hernández
Alberto
A
D000959:Antihypertensive Agents / Q000138:chemical synthesis / Q000737:chemistry*; D003198:Computer Simulation; D019075:Electrophoresis, Capillary; D006863:Hydrogen-Ion Concentration; D008956:Models, Chemical; D009994:Osmolar Concentration; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry*; D011522:Protons; D013056:Spectrophotometry, Ultraviolet
D000959:Antihypertensive Agents; D010636:Phenols; D010880:Piperidines; D011522:Protons; C547111:piperidinylmethylphenol