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Theoretical Study of the Oxidation Catalyst N-Hydroxyphthalimide (NHPI): Thermochemical Properties, Internal Rotor Potential, and Gas- and Liquid-Phase Bond Dissociation Energies
- Source :
- The Journal of Physical Chemistry C. 111:5760-5765
- Publication Year :
- 2007
- Publisher :
- American Chemical Society (ACS), 2007.
-
Abstract
- N-Hydroxyphthalimide (NHPI) has received significant attention in recent years as a catalyst of oxidation synthesis reactions. In this study, we use quantum chemical methods to calculate the molecular geometries, vibrational frequencies, and thermochemical properties of NHPI and the species corresponding to OH hydrogen loss in NHPI, the phthalimide N-oxyl radical (PINO). We also study an analogue of NHPI, N-hydroxymaleimide (NHMI), and we demonstrate that NHPI and NHMI have similar thermochemical properties. G3B3 and CBS-APNO calculations with bond-isodesmic work reactions provide O−H BDEs of 83.3 and 83.5 kcal mol-1 (348.5 and 349.4 kJ mol-1) for NHPI and NHMI, respectively, in the gas phase. Liquid-phase bond energy calculations are performed using the solvents benzene, carbon tetrachloride, acetone, ethanol, DMSO, and acetonitrile with the PCM solvent model. From these liquid-phase G3B3 calculations, we calculate a NHPI O−H BDE of between 83.3 and 83.7 kcal mol-1 (348.5 and 350.2 kJ mol-1) in a variety...
- Subjects :
- Hydrogen
Chemistry
Enthalpy
chemistry.chemical_element
Photochemistry
Bond-dissociation energy
Surfaces, Coatings and Films
Electronic, Optical and Magnetic Materials
Catalysis
chemistry.chemical_compound
General Energy
Catalytic oxidation
Physical and Theoretical Chemistry
Bond energy
Benzene
Acetonitrile
Subjects
Details
- ISSN :
- 19327455 and 19327447
- Volume :
- 111
- Database :
- OpenAIRE
- Journal :
- The Journal of Physical Chemistry C
- Accession number :
- edsair.doi...........dd1b9c46da837283249849f2df1c37f9