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Article

Water Soluble Host–Guest Chemistry Involving Aromatic N-Oxides and Sulfonateresorcinarene

1
Department of Chemistry, Oakland University, 146 Library Drive, Rochester, MI 48309-4479, USA
2
Department of Osteopathic Medicine, Midwestern University, 555 31st St., Downers Grove, IL 60515, USA
3
Faculty of Engineering and Natural Sciences, Tampere University, P.O. Box 541, FI-33101 Tampere, Finland
*
Author to whom correspondence should be addressed.
Symmetry 2020, 12(11), 1751; https://doi.org/10.3390/sym12111751
Received: 30 September 2020 / Revised: 18 October 2020 / Accepted: 19 October 2020 / Published: 22 October 2020
(This article belongs to the Special Issue Recent Advances in Structural and Synthetic Supramolecular Systems)
Resorcinarenes decorated with sulfonate groups are anionic in nature and water soluble with a hydrophobic electron-rich interior cavity. These receptors are shown to bind zwitterionic aromatic mono-N-oxides and cationic di-N-oxide salts with varying spacer lengths. Titration data fit a 1:1 binding isotherm for the mono-N-oxides and 2:1 binding isotherm for the di-N-oxides. The first binding constants for the di-N-oxides (K1: 104 M−1) are higher compared to the neutral mono-N-oxide (K: 103 M−1) due to enhanced electrostatic attraction from a receptor with an electron-rich internal cavity and cationic and electron deficient N-oxides. The interaction parameter α reveals positive cooperativity for the di-N-oxide with a four-carbon spacer and negative cooperativity for the di-N-oxides that have spacers with more four carbons. This is attributed to shape complementarity between the host and the guest. View Full-Text
Keywords: resorcinarenes; N-oxides; cooperative binding; host–guest complex resorcinarenes; N-oxides; cooperative binding; host–guest complex
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MDPI and ACS Style

Twum, K.; Schileru, N.; Elias, B.; Feder, J.; Yaqoo, L.; Puttreddy, R.; Szczesniak, M.M.; Beyeh, N.K. Water Soluble Host–Guest Chemistry Involving Aromatic N-Oxides and Sulfonateresorcinarene. Symmetry 2020, 12, 1751. https://doi.org/10.3390/sym12111751

AMA Style

Twum K, Schileru N, Elias B, Feder J, Yaqoo L, Puttreddy R, Szczesniak MM, Beyeh NK. Water Soluble Host–Guest Chemistry Involving Aromatic N-Oxides and Sulfonateresorcinarene. Symmetry. 2020; 12(11):1751. https://doi.org/10.3390/sym12111751

Chicago/Turabian Style

Twum, Kwaku, Nicholas Schileru, Bianca Elias, Jordan Feder, Leena Yaqoo, Rakesh Puttreddy, Małgorzata M. Szczesniak, and Ngong K. Beyeh 2020. "Water Soluble Host–Guest Chemistry Involving Aromatic N-Oxides and Sulfonateresorcinarene" Symmetry 12, no. 11: 1751. https://doi.org/10.3390/sym12111751

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