Host–Guest Interactions of Sodiumsulfonatomethyleneresorcinarene and Quaternary Ammonium Halides: An Experimental–Computational Analysis of the Guest Inclusion Properties

Abstract

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Recent Advances in Halogen Bonded Assemblies with Resorcin[4]arenes

“…In addition, the OH groups on the upper rim can interact with guest species [12] . In the presence of suitable neutral or ionic guests, resorcinarenes have the ability to form assemblies via weak interactions such as open‐inclusion complexes, [13] dimeric capsules, [14,15] hexameric capsules, [16–18] larger supramolecular and tubular assemblies [19] …”

Intramolecular Hydrogen Bond Driven Conformational Selectivity of Coumarin Derivatives of Resorcin[4]arene

“…Scheme 1 shows the possibilities for controlling the crown- in - out conformations depending on the type of substituent and guest or helper particle introduced. The introduction of a substituent with ionic groups into the molecule favours the complexation of the cationic guest molecule causing a simultaneous conformation change [ 22 ]. Functionalization of resorcin[4]arenes with substituents able to interact through hydrogen bonds, using a helper molecule which exhibits proton-donor-acceptor ability, forces and stiffens the crown- in resorcin[4]arene conformation [ 23 ].…”

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

“…The most notable feature of the receptor is the shallow, electron-rich hydrophobic cavity that binds to the neutral and cationic guest through C-H [8]. This versatility inspired our lab to fundamentally study host-guest complexes using the resorcinarene cavity to extrapolate a structure-property relationship based on guest affinities, conformation, size, and shape [9].…”

“…Appealingly, the negatively charged sulfonate oxygens reinforce the cationic guests by ancillary C-H• • • OSO 2 interactions, a feature that is not available in C2-H-resorcinarenes. The methylene groups between the aromatic ring and the sulfonate groups create an elongated cavity that further helps to improve the guest selectivity [9].…”

“…Herein, we present a host-guest study of sodiumsulfonatomethyleneresorcinarene (1) with three zwitterionic aromatic mono-N-oxides (2)(3)(4), and three cationic di-N-oxide salts with different spacer lengths (5-7) in water ( Figure 1). Our motivation for this study stems from the fact that (i) the elongated cavity compared to basic resorcinarene renders a narrower cavity aperture that influences guest selectivity [9], and that (ii), while aromatic mono-N-oxides are zwitterionic, the di-N-oxides have two cationic binding sites in solution. In effect, we sought answers to the following questions: (a) How does the binding of one site on the di-N-oxide influence binding affinity to the second site?…”