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

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Abstract

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.

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Authors and Affiliations

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

    Jarosł Spychała

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  1. Jarosł Spychała
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Correspondence to Jarosł Spychała.

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Spychała, J. Configurational and conformational preferences in stereoselective acylations of N-methyl-1,3-diaminopropane with acyl chlorides. Res Chem Intermed 33, 481–486 (2007). https://doi.org/10.1163/156856707782565813

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  • DOI: https://doi.org/10.1163/156856707782565813

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