Journal article
Calculated bond dissociation energies and enthalpy of formation of α-amino acid radicals
Theoretical Chemistry Accounts, Vol.135, Article number: 224
2016
Abstract
Bond dissociation energies (BDEs), radical stabilization energies (RSEs) and the enthalpies of formation (Δf H°(AA∙)) for the Cα-centered radical of 20 common α-amino acids were calculated at the G3MP2 level of theory. In addition, BDEs and Δf H°(AA∙) for the Cα-centered radicals were calculated via atomization, homolytic, isogyric and isodesmic reactions using 31 reference compounds. RSEs for the α-amino acid radicals reveal a strong captodative effect due to the resonance stabilization. Intramolecular H-bonding and steric repulsion between the side chains and –NH2 and ‒COOH also have an effect on the stability of α-carbon-centered radicals. For the key small reference compounds investigated, the BDEs (Δf H°(AA∙)) computed with isodesmic reactions were found to be quite consistent with each other in terms of mean absolute deviations (MADs) and root-mean-square deviations between 2.0 (2.6) and 3.2 (4.4) kJ mol−1 from experimental data.
Details
- Title
- Calculated bond dissociation energies and enthalpy of formation of α-amino acid radicals
- Authors/Creators
- K.M. Uddin (Author/Creator) - Murdoch UniversityD.J. Henry (Author/Creator) - Murdoch UniversityR.A. Poirier (Author/Creator) - Memorial University of NewfoundlandP.L. Warburton (Author/Creator) - Memorial University of Newfoundland
- Publication Details
- Theoretical Chemistry Accounts, Vol.135, Article number: 224
- Publisher
- Springer New York
- Identifiers
- 991005541430407891
- Murdoch Affiliation
- School of Engineering and Information Technology
- Language
- English
- Resource Type
- Journal article
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