Continuum Solvation Model Could Explain Why Aqueous Phase Protonation of Nicotine and Nornicotine Occurs on the Pyrrolidine Nitrogen

Mawa Koné Bertrand Illien 1 Christian Laurence 2 Yao T. N'Guessan
1 LCSNSA - Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments
2 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation
Abstract : The Continuum model of solvation IEF-PCM with UAHF or UAO cavity, helps to explain why nicotine and nornicotine protonated on nitrogen SP3 in aqueous phase. Graton et al have shown [1] that the site of protonation of nornicotine is the pyridine nitrogen in the gas phase (NSP2) and is a mixture (NSP2 and NSP3) for nicotine. In this work, we have calculated the free energies of salvation of both entities. The values obtained, show a better solvation of H+NSP3 form than H+NSP2 form either in nicotine or nornicotine. The geometrical parameters of neutral and protonated forms on NSP2 and NSP3 were determined. Significant change between the geometries in vacuo [2] and solvated is an elongation of the intramolecular hydrogen bond N1’…H2 (2.407 to 2.564 Å) and (2.363 to 2.470 Å) for Nicotine and nornicotine respectively. These calculations also showed a better solvation of H + SP3 in nornicotine than nicotine, which explains the highest
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Submitted on : Friday, August 28, 2015 - 3:06:21 PM
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Mawa Koné, Bertrand Illien, Christian Laurence, Yao T. N'Guessan. Continuum Solvation Model Could Explain Why Aqueous Phase Protonation of Nicotine and Nornicotine Occurs on the Pyrrolidine Nitrogen. International Journal of Emerging Technology and Advanced Engineering, 2013, 3 (5), pp.15--23. ⟨hal-01188112⟩

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