Recognition of hydrophilic molecules in deep cavitand hosts with water-mediated hydrogen bonds

Guan, Hua-Wei (author)

Zhu, Yu-Jie (author)

Peters, Joannes (author): Stockholms universitet,Institutionen för organisk kemi

Brea, Oriana (author): Stockholms universitet,Institutionen för organisk kemi

Himo, Fahmi (author): Stockholms universitet,Institutionen för organisk kemi

Rebek, Julius (author)

Yu, Yang (author)

(creator_code:org_t)

2021
2021
English.
In: Chemical Communications. - : Royal Society of Chemistry (RSC). - 1359-7345 .- 1364-548X. ; 57:66, s. 8147-8150

Related links:: https://urn.kb.se/re...; show more...; https://doi.org/10.1...; show less...

Abstract Subject headings

We describe new container host molecules - deep cavitands with benzimidazole walls and ionic feet - to recognize highly hydrophilic guest molecules in water. The aromatic surfaces of the cavity recognize hydrophobic portions of the guest while bound water molecules mediate hydrogen bonding in the complex. Spectroscopic (NMR) evidence indicates slow in/out exchange on the chemical shift timescale and thermodynamic (ITC) methods show large association constants (Ka up to 6 x 10(4) M-1) for complexation of small, water-soluble molecules such as THF and dioxane. Quantum chemical calculations are employed to optimize the host-guest geometries and elucidate the hydrogen bonding patterns responsible for the binding.

By the author/editor: Guan, Hua-Wei; Zhu, Yu-Jie; Peters, Joannes; Brea, Oriana; Himo, Fahmi; Rebek, Julius; show more...; Yu, Yang; show less...

About the subject

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