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1,2,3-Triazoles and the Expanding Utility of Charge Neutral CH···Anion Interactions

  • Kevin P. McDonald
  • Yuran Hua
  • Amar H. Flood
Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 24)

Abstract

As the field of anion supramolecular chemistry continues to grow in its sophistication and understanding of the noncovalent interactions used to effectively bind anions, there exists new theoretical and experimental evidence for a necessary reexamination of the way in which the field views hydrogen bond donors. The heteroatom based hydrogen-bond donors (e.g., NH and OH) are well-known to provide strong stabilization to negatively charged species. However, new findings point to the untapped stabilization energy that lay dormant in extrinsically-activated CH hydrogen bonds. Computational studies showed that an activated aliphatic or aromatic CH can provide an amount of anion stabilization in the gas phase approaching that of conventional NH based donors. Discovery of the Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition to provide 1,2,3-triazoles and the ability to readily “click” this functionality into anion receptors has allowed extensive experimental investigation of the ideas posed by these calculations. This chapter will focus on the evolution of the CH hydrogen bond from being viewed as a weak, secondary interaction to now being utilized as a powerful source of anion stabilization in macrocyclic and oligomeric receptors. In addition, the application of the anion binding power of the 1,2,3-triazole towards the preparation of mechanically interlocked structures will also be discussed.

Keywords

Anion complexation Click chemistry Hydrogen bonding Receptor design Supramolecular chemistry 

Abbreviations

CD

Circular dichroism

DB24C8

Dibenzo[24]crown-8

DIEA

Diisopropylethylamine

DMF

N, N-dimethylformamide

DMSO

Dimethylsulfoxide

ESI-MS

Electrospray ionization mass spectrometry

TBACl

Tetrabutylammonium chloride

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Copyright information

© Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  1. 1.Department of ChemistryIndiana UniversityBloomingtonUSA

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