NDLI: Salt Effects on an Ion–Molecule Reaction—Hydroxide-Catalyzed Hydrolysis of Benzocaine

Content Provider	Springer Nature Link
Author	Al Maaieh, Ahmad Flanagan, Douglas R.
Copyright Year	2006
Abstract	This work investigates the effect of various salts on the rate of a reaction involving a neutral species (benzocaine alkaline hydrolysis).Benzocaine hydrolysis kinetics in NaOH solutions in the presence of different salts were studied at 25°C. Benzocaine solubility in salt solutions was also determined. Solubility data were used to estimate salt effects on benzocaine activity coefficients, and pH was used to estimate salt effects on hydroxide activity coefficients.Salts either increased or decreased benzocaine solubility. For example, solubility increased with 1.0 M tetraethylammonium chloride (TEAC) ∼3-fold, whereas solubility decreased ∼35% with 0.33 M Na$_{2}$SO$_{4}$. Salt effects on hydrolysis rates were more complex and depended on the relative magnitudes of the salt effects on the activity coefficients of benzocaine, hydroxide ion, and the transition state. As a result, some salts increased the hydrolysis rate constant, whereas others decreased it. For example, the pseudo-first-order rate constant decreased ∼45% (to 0.0584 h$^{−1}$) with 1 M TEAC, whereas it increased ∼8% (to 0.116 h$^{−1}$) with 0.33 M Na$_{2}$SO$_{4}$.Different salt effects on degradation kinetics can be demonstrated for a neutral compound reacting with an ion. These salt effects depend on varying effects on activity coefficients of reacting and intermediate species.
Starting Page	589
Ending Page	594
Page Count	6
File Format	PDF
ISSN	07248741
Journal	Pharmaceutical Research
Volume Number	23
Issue Number	3
e-ISSN	1573904X
Language	English
Publisher	Springer-Verlag
Publisher Date	2006-01-01
Publisher Place	New York
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	activity coefficient benzocaine hydrolysis degradation kinetics nonelectrolyte solubility transition state Pharmacology/Toxicology Pharmacy Biochemistry Medical Law Biomedical Engineering
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Pharmacology Molecular Medicine Pharmacology (medical) Biotechnology Pharmaceutical Science

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