Relative Rates of Transesterification vis-à-vis Newman’s Rule of Six
The relative reactivity of a systematic series of simple aliphatic acetate esters has been measured. Exposure of pairs of esters of increasing remote steric hindrance (by altering the degree of branching of the ester alkyl group) to a methanolic solution of Cs<sub>2</sub>CO<sub>3</sub> proved to be a reliable (and general) method for quantitating the rate differences in these base-catalyzed transesterification reactions. The trends in relative rates are in accordance with the qualitative "Rule of Six" put forward by Melvin S. Newman in 1950, as deduced then from interpretation of earlier reports of ease of Fischer esterification reactions.
Authors
- Niklas Kraemer (ORCID: https://orcid.org/0000-0003-4191-109X)
- Thomas R. Hoye (ORCID: https://orcid.org/0000-0001-9318-1477)
- Arianna M. H. Wheeler
- Sei-Chang Ahn
Institutions
- University of Minnesota (US)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-09-06
- DOI
- https://doi.org/10.1021/acs.joc.4c01673
- Primary Topic
- Inorganic and Organometallic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Science Foundation
- University of Minnesota
- National Institutes of Health
- Division of Chemistry