The "Nitrogen Effect": Complexation with Macrocycles Potentiates Fused Heterocycles to Form Halogen Bonds in Competitive Solvents

Kwaku Twum; Sanaz Nadimi; Frank Boateng Osei; Rakesh Puttreddy; Yvonne Bessem Ojong; John J Hayward; Kari Rissanen; John F Trant; Ngong Kodiah Beyeh

doi:10.1002/asia.202201308

The "Nitrogen Effect": Complexation with Macrocycles Potentiates Fused Heterocycles to Form Halogen Bonds in Competitive Solvents

Chem Asian J. 2023 Mar 14;18(6):e202201308. doi: 10.1002/asia.202201308. Epub 2023 Feb 7.

Authors

Kwaku Twum¹, Sanaz Nadimi², Frank Boateng Osei¹, Rakesh Puttreddy³, Yvonne Bessem Ojong¹, John J Hayward², Kari Rissanen³, John F Trant², Ngong Kodiah Beyeh¹

Affiliations

¹ Department of Chemistry, Oakland University, 146 Library Drive, Rochester, Michigan, 48309, USA.
² Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Avenue, Windsor, Ontario, N9B 3P4, Canada.
³ Department of Chemistry, University of Jyvaskyla, Survontie 9 B, FI-40014, Jyvaskyla, Finland.

PMID: 36705487
DOI: 10.1002/asia.202201308

Abstract

Weak intermolecular forces are typically very difficult to observe in highly competitive polar protic solvents as they are overwhelmed by the quantity of competing solvent. This is even more challenging for three-component ternary assemblies of pure organic compounds. In this work, we overcome these complications by leveraging the binding of fused aromatic N-heterocycles in an open resorcinarene cavity to template the formation of a three-component halogen-bonded ternary assembly in a protic polar solvent system.

Keywords: Dimeric capsules; Halogen bond; N-Heterocycles; Resorcinarenes; Ternary assemblies.

Abstract

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