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Topomeric Aza/Thia Cryptands: Synthesis and Theoretical Aspects of In/Out Isomerism using n-Alkyl Bridging

Abstract

A series of heterobicyclic aza/thia-lactams and cryptands incorporating changes in n-alkyl bridging length have been synthesized, characterized, and computationally assessed. Spectroscopic analysis of aza/thia-lactams L1 and L3 revealed multiple conformational isomers, due to rotameric perturbations associated with the amide bond. Correlation spectroscopy on amine cryptands L2 and L4 supported the presence of intrinsic topological chirality, resulting from a preferred orientation of the amine lone pairs in solution. The unique magnetic environments observed in 1H NMR were attributed to the electron density inside the crypt, which adopt a nephroidal-epicycloid structure with two nitrogen atoms representing the cusps. The major conformational and constitutional isomers present in solution were determined to be the in/in pair of enantiomers (R,R and S,S) and confirmed through computational analysis.

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Article information


Submitted
24 Jan 2020
Accepted
15 Mar 2020
First published
17 Mar 2020

Org. Chem. Front., 2020, Accepted Manuscript
Article type
Research Article

Topomeric Aza/Thia Cryptands: Synthesis and Theoretical Aspects of In/Out Isomerism using n-Alkyl Bridging

I. S. Taschner, T. L. Walker, S. C. Mallojjala, B. Schrage, C. Ziegler, X. Gao and S. Wheeler, Org. Chem. Front., 2020, Accepted Manuscript , DOI: 10.1039/D0QO00123F

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