Work

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

Year: 2024

Type: article

Abstract: Widely cited values of 89 and 90.9 kcal/mol for the bond-dissociation free energy of N -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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c01734

Authors: James B. Gerken, Shannon L. Goes, Paige E. Piszel, Abdullah J. Al Abdulghani, Ive Hermans, Shannon S. Stahl

Institution: University of Wisconsin–Madison

Language: English

Topic: Chemical Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, Basic Energy Sciences

Awards: G4301586875, Acquisition of a 400 MHz NMR Spectrometer for Chemical Research and Learning