Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5419248 | Journal of Molecular Structure: THEOCHEM | 2007 | 7 Pages |
Abstract
DFT calculations employing the SCRF-B3LYP/6-311+G(d) level of theory have been employed in order to quantitatively characterize the mechanism of the ring-opening reaction of (s)-1-benzyl-2-methyl-aziridine and an iminium salt to a 1,2-diamine, in the presence of lithium iodide. Computational results indicate that the optimal reaction pathway may proceed via an aziridinium cation intermediate mechanism, rather than by an SN2 mechanism. Self-consistent reaction field (SCRF) calculations, using the PCM model and THF as solvent, showed an energetic barrier for aziridine ring-opening to be on the order of â¼10.9Â kcal/mol; indicating the process to be thermodynamically spontaneous. The catalytic role of Iâ and substituent effects are also elaborated upon herein.
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Authors
Wei-Hua Mu, Chao Wang, De-Cai Fang,