Evidence for a stereoinduction profile of the reaction of N-methyl-1,3-diaminopropane with acyl chlorides has been provided. A possibility to engage in intramolecular CH2⋯HN and Cl⋯H-N interactions and the proton migration process to the methylamino group leads to the E secondary amides carrying the N⋯H+⋯N or N-H⋯N bridges, that show unusual spectroscopic images. Empirical relations between the Δδ C chemical shift differences, the polarizability of the CO(S) groups and hydrogen bonding strength have been found. Both 1H-15N-GHSQC and GHMBC experiments provide insight into the nature of hydrogen bonding and confirm the cyclic array of atoms.
Research on Chemical Intermediates – Springer Journals
Published: Jan 1, 2007
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