Hydrolysis rates of some acetylimidazole derivatives
Open accessAbstract
N-Acetylbenzimidazole (4), N-acetyl-N′-methylbenzimidazolium acetate (5), and N-acetyl-N′-methyltetrahydrobenzimidazolium acetate (6) were synthesized and their hydrolysis rates were studied.
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N-alkyl-imidazoles are hydrolytically unstable and react under water-catalyzed, base-catalyzed, or acid-catalyzed reaction mechanisms.
“N-alkyl-imidazoles are hydrolytically unstable and they react under water-catalyzed, base-catalyzed (Figure 9), or acid-catalyzed (Figure 10) reaction mechanisms [33,34].”
From Degradation Kinetics of Clavulanic Acid in Fermentation Broths at Low Temperatures (2019) · cites this paper as [33]
The Abstract describes water-catalyzed hydrolysis of an acetylimidazolium ion, and the Results and discussion report pH-dependent hydrolysis of N-acetyl derivatives, including N-acetyl-N′-methylbenzimidazolium acetate (pages unavailable in our copy). The rate laws show acid-, pH-independent-, and hydroxide-dependent contributions for particular acetyl derivatives, but the paper does not establish that N-alkyl-imidazoles generally are hydrolytically unstable or undergo all three mechanisms. (LLM, conf=0.86)
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Research works printed but not linked: 8
- W. P. JENCKS and J. CARRIUOLO. J. Biol. Chem. 234, 1272 (1959);
- R. WOLFENDEN and W. P. JENCKS. J. Am. Chem. Soc. 83,4390 (1961);
- S. M. MARLUURG and W. P. JENCKS. J. Am. Chem. Soc. 84, 232 (1962).
- J. L. HOCG, M. K. PHILLIPS, and D. E. JERGENS. J. Org. Chem. 42, 2459 (1977);
- J. L. HOGG and W. P. HUSKEY. J. Org. Chem. 46, 53 (1981).
- L. BUTULA. Croat. Chcm. Acta, 45, 297 (1973).
- A. ALBERT and E. P. SERJEANT. In Ionization constants of acids and bases. J. Wiley and Sons, New York. 1962.
- T. C. BRUICE and G. L. SCHMIR. J. Am. Chem. Soc. 79, 1663 (1957).
Cited by
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Degradation Kinetics of Clavulanic Acid in Fermentation Broths at Low Temperatures
Gómez-Ríos, D., Ramírez-Malule, H., Neubauer, P., Junne, S., & Ríos-Estepa, R. (2019) · Antibiotics · doi:10.3390/antibiotics8010006 · Cited by 17 · see citing works
“N-alkylimidazoles are hydrolytically unstable and they react under water-catalyzed, base-catalyzed (Figure 9), or acid-catalyzed (Figure 10) reaction mechanisms [33,34].”
Background
- Authors
- Gour-Salin, B. J.
- Corresponding author
- Gour-Salin, B. J.
- Venue
- Canadian Journal of Chemistry
- Publisher
- Canadian Science Publishing
- Published
- 1983-09-01
- Volume
- 61
- Issue
- 9
- Pages
- 2059-2061
- ISSN
- 0008-4042 (ISSN-L)
- 1480-3291
- OpenAlex
- W2084216936
- Cited by
- 7
- References
- 0
- Citations by year
- 2023: 1 · 2022: 1 · 2019: 1 · 2016: 1
- FWCI
- 0.00
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- Canadian Journal of Chemistry (publishedVersion)
- Funders
- University of Alberta
- Natural Sciences and Engineering Research Council of Canada
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Reactions of Organic Compounds
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Synthetic Organic Chemistry
- Keywords
- hydrolysis rate, benzimidazolium salts, hydrolysis kinetics
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