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Protonation sites in methyl nitrate (1) were evaluated computationally at the Gaussian 2(MP2) level of ab initio theory. The methoxy oxygen was the most basic site that had a calculated proton affinity of PA = 728–738 kJ mol−1 depending on the optimization method used to calculate the equilibrium geometry of the CH3O(H)-NO 2+ ion (2+). Protonation at the terminal oxygen atoms in methyl nitrate was...
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