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Configurational and conformational preferences in stereoselective acylations of N-methyl-1,3-diaminopropane with acyl chlorides

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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 ΔδC 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.

Affiliations: 1: Department of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland


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