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Comparative Analysis of Acyclovir Esters Stability in Solutions: The Influence of the Substituent Structure, Kinetics, and Steric Effects
Author(s) -
Lesniewska Monika A.,
Gola Michał,
Dutkiewicz Zbigniew,
Muszalska Izabela
Publication year - 2015
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/kin.20943
Subject(s) - chemistry , steric effects , substituent , hydrolysis , acetonitrile , acetic acid , selectivity , chromatography , catalysis , kinetics , high performance liquid chromatography , phosphate , medicinal chemistry , organic chemistry , physics , quantum mechanics
Reversed‐phase high‐performance liquid chromatography has been applied to the determination of acyclovir (ACV) esters such as acetate, iso butyrate, pivalate, ethoxycarbonate, and nicotinate. All analyses were carried out at laboratory temperature using a column LiChrospher RP‐18 (250 × 4 mm, 5 µm) and a proper mobile phase consisting of acetonitrile and phosphate buffer (pH 6 or 6.7) or acetonitrile and potassium dihydrogen phosphate, and acetic acid. The methods were validated by the determination of the following parameters: selectivity, precision, accuracy, and linearity. Kinetic studies on the hydrolysis were investigated in solutions at 310 K over the pH range 0.42–1.38. The pH‐profiles indicated specific acid‐catalyzed and spontaneous water‐catalyzed degradation. The stability of the studied ACV esters were determined not only by steric factors. In the case of ethoxycarbonyl ester of ACV, the hydrolysis was a two‐step reaction.