A computational mechanistic study of the deamination reaction of melamine

M.H. Almatarneh; A.A-A.A. Abu-Saleh; K.M. Uddin; R.A. Poirier; P.L. Warburton

doi:10.1002/qua.25308

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A computational mechanistic study of the deamination reaction of melamine

Journal article

Peer reviewed

A computational mechanistic study of the deamination reaction of melamine

M.H. Almatarneh, A.A-A.A. Abu-Saleh, K.M. Uddin, R.A. Poirier and P.L. Warburton

International Journal of Quantum Chemistry, Vol.117(3), pp.180-189

2016

DOI: https://doi.org/10.1002/qua.25308

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Abstract

A detailed computational study of the deamination reaction of melamine by OH–, nH2O/OH–, nH2O (where n = 1, 2, 3), and protonated melamine with H2O, has been carried out using density functional theory and ab initio calculations. All structures were optimized at M06/6-31G(d) level of theory, as well as with the B3LYP functional with each of the basis sets: 6-31G(d), 6-31 + G(d), 6-31G(2df,p), and 6-311++G(3df,3pd). B3LYP, M06, and ωB97XD calculations with 6-31 + G(d,p) have also been performed. All structures were optimized at B3LYP/6-31 + G(d,p) level of theory for deamination simulations in an aqueous medium, using both the polarizable continuum solvation model and the solvation model based on solute electron density. Composite method calculations have been conducted at G4MP2 and CBS-QB3. Fifteen different mechanistic pathways were explored. Most pathways consisted of two key steps: formation of a tetrahedral intermediate and in the final step, an intermediate that dissociates to products via a 1,3-proton shift. The lowest overall activation energy, 111 kJ mol−1 at G4MP2, was obtained for the deamination of melamine with 3H2O/OH−.

Details

Title: A computational mechanistic study of the deamination reaction of melamine
Authors/Creators: M.H. Almatarneh (Author/Creator) - University of Jordan
A.A-A.A. Abu-Saleh (Author/Creator) - University of Jordan
K.M. Uddin (Author/Creator) - The University of Western Australia
R.A. Poirier (Author/Creator) - Department of ChemistryMemorial UniversitySt. John's NL,A1B 3X7 Canada
P.L. Warburton (Author/Creator) - Department of ChemistryMemorial UniversitySt. John's NL,A1B 3X7 Canada
Publication Details: International Journal of Quantum Chemistry, Vol.117(3), pp.180-189
Publisher: John Wiley and Sons Inc.
Identifiers: 991005541556907891
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; 2.244 Chemometrics; 2.244.2133 Molecular Authentication
Web Of Science research areas: Chemistry, Physical; Mathematics, Interdisciplinary Applications; Physics, Atomic, Molecular & Chemical; Quantum Science & Technology
ESI research areas: Chemistry