Journal article
Mechanism for the deamination of ammeline, guanine, and their analogues
Structural Chemistry, Vol.28(5), pp.1467-1477
2017
Abstract
Mechanisms for the deamination of ammeline (AMN), guanine (Gua), and their analogues with nH2O (n = 1–3) have been investigated using B3LYP and G3MP2B3. The deamination reactions of AMN and Gua with 3H2O/OH−, and protonated AMN and Gua with 3H2O, were investigated using DFT. The rationale behind this work was to compare the deamination reactions of AMN and Gua analogues. Optimized geometries of the reactants, transition states, intermediates, and products were determined at B3LYP/6-31G(d,p) level of theory, and solvent calculations were performed using the solvation model on density (SMD). Thermodynamic properties (ΔH, and ΔG), proton affinities (PAs), gas-phase basicities (GBs), deprotonation enthalpies (ΔacidH), and gas-phase acidities (ΔacidG) were also calculated. For the SN2 mechanism, deamination can proceed via two possible pathways involving either two- or three-stepwise mechanisms producing a tetrahedral intermediate via four-, six-, or eight-membered transition states. The lowest overall activation energies of 128 (131) and 131 (133) kJ mol−1 at B3LYP/6-31G(d,p) in the gas phase (SMD) were obtained for the deamination of AMN and Gua with 3H2O, whereas the values of 140 (115) and 139 (117) kJ mol−1 were obtained for AMN and Gua with 3H2O/OH−, respectively. For protonated AMN and Gua with 3H2O in the gas phase (SMD), the overall activation energies are 233 (155) and 240 (162) kJ mol−1, respectively.
Details
- Title
- Mechanism for the deamination of ammeline, guanine, and their analogues
- Authors/Creators
- K.M Uddin (Author/Creator) - Murdoch UniversityD.J. Henry (Author/Creator) - Murdoch UniversityA. I. Alrawashdeh (Author/Creator) - Memorial University of NewfoundlandP.L. Warburton (Author/Creator) - Memorial University of NewfoundlandR.A. Poirier (Author/Creator) - Memorial University of Newfoundland
- Publication Details
- Structural Chemistry, Vol.28(5), pp.1467-1477
- Publisher
- Springer Verlag
- Identifiers
- 991005544507907891
- Copyright
- © Springer Science+Business Media New York 2017
- Murdoch Affiliation
- School of Engineering and Information Technology
- Language
- English
- Resource Type
- Journal article
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