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- W2142269989 abstract "The reaction of methylamine with acetaldehyde in pentane at 230 K leads to formation of both E- and Z- aldimines, the Z-isomer being the main product and generated upon kinetic control. The E- form is more stable than the Z- form by 3.3 kcal/mol (deltaG*). Ab initio calculations have indicated that a tetrahedral zwitterion intermediate is not formed, and the bimolecular process, forming the aminoalcohol intermediate, occurs through a four center transition state, with concerted formation of C-N bond and proton transfer. However, the predicted deltaG*<FONT FACE=Symbol>¹</FONT> is very high, indicating that the true mechanism for this step is not bimolecular. A catalyzed pathway must be actuating. The following step, unimolecular elimination of water, also presents a very high activation free energy. Similarly, a catalyzed mechanism is needed. The isomerization from the Z- form to the E- form through inversion of the nitrogen atom has a predicted deltaG*<FONT FACE=Symbol>¹</FONT> of 27.0 kcal/mol at 298.15 K, resulting in a lifetime of four months for the Z-isomer." @default.
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- W2142269989 date "1999-10-01" @default.
- W2142269989 modified "2023-10-14" @default.
- W2142269989 title "Theoretical and experimental investigation of the formation of E- and Z-Aldimines from the reaction of methylamine with acetaldehyde" @default.
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- W2142269989 doi "https://doi.org/10.1590/s0103-50531999000500008" @default.
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