IMN

Biblio. IMN

Référence en vue solo

Locati, A., Berthelot, M., Evain, M., Lebreton, J., Le Questel, J.-Y., Mathe-Allainmat, M., Planchat, A., Renault, E. & Graton, J. (2007) The exceptional hydrogen-bond properties of neutral and protonated lobeline. J. Phys. Chem. A, 111 6397–6405. 
Added by: Laurent Cournède (2016-03-10 22:02:29)
Type de référence: Article
DOI: 10.1021/jp071632b
Numéro d'identification (ISBN etc.): 1089-5639
Clé BibTeX: Locati2007
Voir tous les détails bibliographiques
Catégories: MIOPS
Mots-clés: acetylcholine, basicity pk(hb) scale, binding protein, complexation, crystal-structure, fermi resonance, log k-values, nicotinic pharmacophore, partition-coefficients, tertiary-amines
Créateurs: Berthelot, Evain, Graton, Le Questel, Lebreton, Locati, Mathe-Allainmat, Planchat, Renault
Collection: J. Phys. Chem. A
Consultations : 7/431
Indice de consultation : 1%
Indice de popularité : 0.25%
Résumé     
The X-ray diffraction structure of (-)-lobeline, a high affinity nicotinic ligand, has been determined. A comparison with its hydrobromide and hydrochloride salts shows the great flexibility of the two lateral chains of the N-methylpiperidine ring. Infrared studies carried out on the same species, in the solid state and in solution, reveal the propensity of this molecular framework to accommodate very specific hydrogen bonds (HBs) depending on the stateneutral or protonatedof the molecule. In solution, a strong internal HB between the hydroxyl group and the piperidine nitrogen gives an exceptionally high HB affinity to the hydroxyl oxygen of the lobeline base. In the ionic form, both NH+ and OH groups of the molecule cooperate as HB donors to chelate the counterion. These interactions provide very stable structures and indicate that protonated lobeline can also act as a strong HB donor.
Added by: Laurent Cournède  
wikindx 4.2.2 ©2014 | Références totales : 2525 | Requêtes métadonnées : 65 | Exécution de script : 0.11502 secs | Style : Harvard | Bibliographie : Bibliographie WIKINDX globale