Publication: "Push-pull" effects in nitroethenamines
"Push-pull" effects in nitroethenamines
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Linden, A., Moya Argilagos, D., Heimgartner, H., Garcia Trimino, M. I., & Macias Cabrera, A. (1999). “Push-pull” effects in nitroethenamines. Acta Crystallographica. Section C: Crystal Structure Communications, 55, 1692–1698. https://doi.org/10.1107/S0108270199006861
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(E)-N-methyl-1-(methylthio)-2-nitroethenamine, C4H8N2O2S, is a near-planar molecule with significant pi-electron delocalization from the ethylene bond into the enamine C-N bond. In the two nitrothioacrylamide derivatives, N-benzoyl-3,3-bis(methylamino)-2-nitrothioacrylamide, C12HI4N4O3S, and N-cinnamoyl-3,3-bis(dimethylamino)-2-nitrothioacrylamide, C16H20N4O3S, the formal ethylene bond has single-bond properties with a length of about 1.49 A, while the magnitudes of the torsion angles about this bond approach 90°. The enamine N-C bond
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F. Hoffmann-La Roche AG, Basel
Swiss Federal Government (Bundesstipendium)
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Linden, A., Moya Argilagos, D., Heimgartner, H., Garcia Trimino, M. I., & Macias Cabrera, A. (1999). “Push-pull” effects in nitroethenamines. Acta Crystallographica. Section C: Crystal Structure Communications, 55, 1692–1698. https://doi.org/10.1107/S0108270199006861