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Solvent Effects on Protonation Process of Clindamycin in Mixed Solvents


Affiliations
1 Department of Chemistry, Ayatollah Amoli Branch, Islamic Azad University, Amol, Iran, Islamic Republic of
2 Department of Chemistry, Jouybar Branch, Islamic Azad University, Jouybar, Iran, Islamic Republic of
3 Division of Computational Physics, Institute for Computational Science, Ton Duc Thang University, Ho Chi Minh City, Viet Nam
 

Clindamycin is used in the treatment of bacterial infections. The protonation constant of this drug was determined in mixed solvents of water and methanol as well as water and ethanol in the volume range 0–50 (% v/v) at 298.15 K and 0.1 M NaClO4 as the inert electrolyte. The results show that in both mixed solvents, pKa decreases when the volume fraction of alcohols increases. We considered the effect of the solvent on equilibrium constants using the electrostatic model of Born and the linear solvation energy relationship model developed by Kamlet and Taft. The results indicate that both hydrogen-bonding interactions and electrostatic interactions give rise to the observed changes. Using the derived equations, it is possible to determine pKa of clindamycin in the desired composition throughout the studied range.

Keywords

Antibiotic Drugs, Ethanol, Methanol, Protonation Constant, Solvent Effect.
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  • Solvent Effects on Protonation Process of Clindamycin in Mixed Solvents

Abstract Views: 271  |  PDF Views: 123

Authors

Fatemeh Farrokhmanesh
Department of Chemistry, Ayatollah Amoli Branch, Islamic Azad University, Amol, Iran, Islamic Republic of
Farhoush Kiani
Department of Chemistry, Ayatollah Amoli Branch, Islamic Azad University, Amol, Iran, Islamic Republic of
Ali Farajtabar
Department of Chemistry, Jouybar Branch, Islamic Azad University, Jouybar, Iran, Islamic Republic of
Fardad Koohyar
Division of Computational Physics, Institute for Computational Science, Ton Duc Thang University, Ho Chi Minh City, Viet Nam
Seyed Hassan Noshirvankolaei
Department of Chemistry, Ayatollah Amoli Branch, Islamic Azad University, Amol, Iran, Islamic Republic of

Abstract


Clindamycin is used in the treatment of bacterial infections. The protonation constant of this drug was determined in mixed solvents of water and methanol as well as water and ethanol in the volume range 0–50 (% v/v) at 298.15 K and 0.1 M NaClO4 as the inert electrolyte. The results show that in both mixed solvents, pKa decreases when the volume fraction of alcohols increases. We considered the effect of the solvent on equilibrium constants using the electrostatic model of Born and the linear solvation energy relationship model developed by Kamlet and Taft. The results indicate that both hydrogen-bonding interactions and electrostatic interactions give rise to the observed changes. Using the derived equations, it is possible to determine pKa of clindamycin in the desired composition throughout the studied range.

Keywords


Antibiotic Drugs, Ethanol, Methanol, Protonation Constant, Solvent Effect.



DOI: https://doi.org/10.18520/cs%2Fv119%2Fi2%2F374-377