When the amide-contg. receptor (I) is in a soln. of DMSO (DMSO) in the presence of basic anions (CH3COO-, F-, H2PO4-), it undergoes deprotonation of the -NH fragment to give the corresponding zwitterion, which can be isolated as a cryst. solid. In the presence of less basic anions (Cl-, Br-, NO3-), I establishes true hydrogen-bond interactions of decreasing intensity. The less acidic receptor II undergoes neat proton transfer with only the more basic anions CH3COO- and F-, and establishes hydrogen-bond interactions with H2PO4-. An empirical criterion for discerning neutralization and hydrogen bonding, based on UV/Vis and 1H NMR spectra, is proposed.

Anion receptors containing -NH binding sites: hydrogen-bond formation or neat proton transfer

AMENDOLA, VALERIA;BOIOCCHI, MASSIMO;FABBRIZZI, LUIGI;
2005-01-01

Abstract

When the amide-contg. receptor (I) is in a soln. of DMSO (DMSO) in the presence of basic anions (CH3COO-, F-, H2PO4-), it undergoes deprotonation of the -NH fragment to give the corresponding zwitterion, which can be isolated as a cryst. solid. In the presence of less basic anions (Cl-, Br-, NO3-), I establishes true hydrogen-bond interactions of decreasing intensity. The less acidic receptor II undergoes neat proton transfer with only the more basic anions CH3COO- and F-, and establishes hydrogen-bond interactions with H2PO4-. An empirical criterion for discerning neutralization and hydrogen bonding, based on UV/Vis and 1H NMR spectra, is proposed.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/143383
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