Calculated bond dissociation energies and enthalpy of formation of α-amino acid radicals

K.M. Uddin; D.J. Henry; R.A. Poirier; P.L. Warburton

doi:10.1007/s00214-016-1975-9

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Calculated bond dissociation energies and enthalpy of formation of α-amino acid radicals

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Peer reviewed

Calculated bond dissociation energies and enthalpy of formation of α-amino acid radicals

K.M. Uddin, D.J. Henry, R.A. Poirier and P.L. Warburton

Theoretical Chemistry Accounts, Vol.135, Article number: 224

2016

DOI: https://doi.org/10.1007/s00214-016-1975-9

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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 University
D.J. Henry (Author/Creator) - Murdoch University
R.A. Poirier (Author/Creator) - Memorial University of Newfoundland
P.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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Collaboration types: Domestic collaboration; International collaboration
Citation topics: 2 Chemistry; 2.211 Mass Spectrometry; 2.211.304 Mass Spectrometry Advances
Web Of Science research areas: Chemistry, Physical
ESI research areas: Chemistry