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Recognition of hydr...
Recognition of hydrophilic molecules in deep cavitand hosts with water-mediated hydrogen bonds
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Guan, Hua-Wei (author)
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Zhu, Yu-Jie (author)
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- Peters, Joannes (author)
- Stockholms universitet,Institutionen för organisk kemi
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- Brea, Oriana (author)
- Stockholms universitet,Institutionen för organisk kemi
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- Himo, Fahmi (author)
- Stockholms universitet,Institutionen för organisk kemi
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Rebek, Julius (author)
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Yu, Yang (author)
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(creator_code:org_t)
- 2021
- 2021
- English.
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In: Chemical Communications. - : Royal Society of Chemistry (RSC). - 1359-7345 .- 1364-548X. ; 57:66, s. 8147-8150
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- 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.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Publication and Content Type
- ref (subject category)
- art (subject category)
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