Abstract
Monomethylnitrosamine and methyldiazohydroxide are two proposed N-nitrosamine metabolites, which are formally related by an N → O 1,3-proton shift. Their possible interconversion is an important reaction to investigate in elucidating the pathways involved in the decomposition of carcinogenic N-nitrosamines. Self-consistent field molecular orbital studies using a 4-21G basis set, in which solvation is treated using the supermolcule approach, have led to the proposal of a new low energy pathway for their interconversion; this mechanism involves protonation and the implicit involvement of at least two molecules of water.
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Reynolds, C.A., Thomson, C. Ab-initio molecular orbital studies on a new mechanism for the interconversion of monomethylnitrosamine and methyldiazohydroxide. Theoret. Chim. Acta 70, 421–427 (1986). https://doi.org/10.1007/BF00531923
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DOI: https://doi.org/10.1007/BF00531923