Configurational and Conformational Preferences in Stereoselective Acylations of N-Methyl-1,3-diaminopropane with Acyl Chlorides

Jaroslaw Spychala

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

Configurational and Conformational Preferences in Stereoselective Acylations of N-Methyl-1,3-diaminopropane with Acyl Chlorides

Abstract

Evidence for a stereoinduction profile of the reaction of N-methyl-1,3-diaminopropane with acyl chlorides was provided. A possibility to engage in intramol. 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 chem. shift differences, the polarizability of the CO(S) groups and hydrogen bonding strength were 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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Jaroslaw Spychala dr

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Category:: Magazine publication
Type:: Magazine publication
Published in:: RESEARCH ON CHEMICAL INTERMEDIATES no. 33, edition 6, pages 481 - 486,
ISSN: 0922-6168
Publication year:: 2007
Bibliographic description:: Jaroslaw Spychala, Configurational and Conformational Preferences in Stereoselective Acylations of N-Methyl-1,3-diaminopropane with Acyl Chlorides, Research on Chemical Intermediates, vol. 33(6), pages 481-486, 2007.
DOI:: Digital Object Identifier (open in new tab) https://doi.org/10.1163/156856707782565813
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