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

Configurational and conformational preferences in stereoselective acylations of... 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

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

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Publisher
Brill Academic Publishers
Copyright
Copyright © 2007 by VSP
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1163/156856707782565813
Publisher site
See Article on Publisher Site

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.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Jan 1, 2007

References

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