Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5395155 | Computational and Theoretical Chemistry | 2011 | 5 Pages |
Abstract
The thermal reaction mechanisms of fluorobutanesulfonyl azide with pyrazine under solvent free condition have been studied by density functional theory (DFT) in this paper. Four possible reaction channels including two stepwise channels (channels 1 and 2) and the other two concerted channels (channels 3 and 4) are shown. The calculated results indicate that the stepwise channels (channels 1 and 2) should be easier to occur than the concerted channels (channels 3 and 4), and one of the stepwise channels (channel 1) is the most energy favorable reaction path among all the four possible channels, thus, the main product should be the pyrazinium N-fluorobutanesulfonyl ylide, which is consistent with the experimental result. Moreover, the highest energy barrier of channel 1 is 35.10Â kcal/mol at the B3LYP/6-31G (d, p) level (which is 33.97Â kcal/mol at the B3LYP/6-311++G (2d, 2p) level), this should be not a very high energy barrier for the experimental temperature (418Â K). Furthermore, there are very small differences between the calculated results of two different levels. Therefore, it should be reliable that the stepwise reaction channel is the main reaction path in this reaction.
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Authors
Donghui Wei, Liangguang Wang, Mingsheng Tang,