The Aqueous and Acetonitrile Bond Dissociation Free Energies of -Hydroxyphthalimide.

J Org Chem

Department of Chemistry, University of Wisconsin─Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.

Published: November 2024

Widely cited values of 89 and 90.9 kcal/mol for the bond-dissociation free energy of -hydroxyphthalimide (NHPI) in water and acetonitrile, respectively, are in error. The sources of the errors leading to these values have been explored and corrected. The corrected values are confirmed through new experiments in aqueous and acetonitrile media and are found to be 84.4 ± 0.1 and 80.04 ± 0.06 kcal/mol, respectively.

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http://dx.doi.org/10.1021/acs.joc.4c01734DOI Listing

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