The conformational landscape of nicotinoids: solving the conformational disparity of anabasine

Chemistry : a European Journal
Alberto LesarriJens-Uwe Grabow

Abstract

The conformational landscape of the alkaloid anabasine (neonicotine) has been investigated by using rotational spectroscopy and ab initio calculations. The results allow a detailed comparison of the structural properties of the prototype piperidinic and pyrrolidinic nicotinoids (anabasine vs. nicotine). Anabasine adopts two most stable conformations in isolation conditions, for which we determined accurate rotational and nuclear quadrupole coupling parameters. The preferred conformations are characterized by an equatorial pyridine moiety and additional N-H equatorial stereochemistry at the piperidine ring (eq-eq; eq=equatorial). The two rings of anabasine are close to a bisecting arrangement, with the observed conformations differing by an approximately 180 degrees rotation of the pyridine subunit, denoted either syn or anti. The preference of anabasine for the eq-eq-syn conformation has been established by relative intensity measurements (syn/anti approximately 5(2)). The conformational preferences of free anabasine are directed by a weak N...H-C hydrogen bond interaction between the nitrogen lone pair at piperidine and the closest C-H bond in pyridine, with N...H distances ranging from 2.686 (syn) to 2.667 A (anti). Supportin...Continue Reading

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Citations

May 3, 2011·The Journal of Chemical Physics·Patricia ÉcijaFernando Castaño
Mar 29, 2013·The Journal of Chemical Physics·Patricia ÉcijaFernando Castaño
Oct 25, 2011·Physical Chemistry Chemical Physics : PCCP·Jens-Uwe GrabowC Cabezas
Dec 12, 2012·Toxicology and Applied Pharmacology·Kevin D WelchDale R Gardner
Dec 18, 2013·Birth Defects Research. Part C, Embryo Today : Reviews·Benedict T GreenKip E Panter
Jun 11, 2015·Journal of Molecular Graphics & Modelling·P G Rodríguez OrtegaJ J López González
Mar 28, 2012·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Benedict T GreenDavid R Brown
Feb 18, 2017·Chemistry : a European Journal·Iciar UriarteEmilio J Cocinero
Mar 25, 2015·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Pilar G Rodríguez OrtegaJuan J López González
May 4, 2013·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Patricia ÉcijaFernando Castaño
Jan 4, 2012·Angewandte Chemie·Emilio J CocineroFernando Castaño
Jun 16, 2011·The Journal of Physical Chemistry. a·Luca EvangelistiJens-Uwe Grabow
Sep 14, 2013·The Journal of Physical Chemistry. a·Michaela K JahnJens-Uwe Grabow

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