Hydrogen-bond accepting strength of protonated nicotine.

Michel Berthelot, Jean-Yves Le Questel, Virginie Arnaud

Journal: The journal of physical chemistry. A 2007;109(17):3767-70

PMID: 16833690

Full Text on American Chemical Society View on PubMed

Abstract

Recent crystal structures of nicotine bound to the acetylcholine binding protein (AChBP) ended a long debate confirming that the pyridine nitrogen of nicotine is indeed hydrogen-bonded to receptor residues through a bridging water molecule. Here, we describe the first direct experimental evaluation of the hydrogen-bond affinity of the nicotinium pyridine nitrogen. The equilibrium constant of its association with a phenol is 1 order of magnitude greater than the association of the acetylcholine carbonyl oxygen.

DOI: 10.1021/jp051391c

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MeSH Terms: Acetylcholine, Chemistry, Physical, Densitometry, Hydrogen Bonding, Kinetics, Methylene Chloride, Models, Chemical, Models, Molecular, Nicotine, Nitrogen, Oxygen, Phenol, Protons, Pyridines, Thermodynamics