Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10637/10592
Título : Stereodynamics and Edge-to-Face CH-π aromatic interactions in imino compounds containing heterocyclic rings
Autor : González Rosende, María Eugenia.
Castillo García, Encarnación.
Jennings, W. Brian.
Malone, John F.
Materias: Compuestos heterocíclicos.Chemistry, Organic.Química orgánica.Heterocyclic compounds.
Fecha de publicación : 17-ene-2017
Editorial : Royal Society of Chemistry
Citación : González-Rosende, ME., Castillo García, E., Jennings, WB. & Malone, JF. (2017). Stereodynamics and Edge-to-Face CH-π aromatic interactions in imino compounds containing heterocyclic rings. Organic & Biomolecular Chemistry, n. 6. DOI: https://doi.org/10.1039/C6OB02618D
Resumen : By comparison with close contact interactions between benzene rings there is a paucity of experimental data available for attractive interactions involving aromatic heterocyclic rings, especially for small molecules in solution. Herein we describe aromatic heterocyclic and carbocyclic edge-to face interactions and conformational stereodynamics of N-1,2-diphenylethyl imines bearing a phenyl group and either a 2-pyridyl, 3-pyridyl, 2-thiophene or 2-furanyl moiety on the imino carbon. X-ray crystal structures have been determined for two compounds. Slow rotation about the phenyl–imino bond in the E-isomers and around the heterocycle–imino bond in the Z-isomers of the pyridyl compounds was observed at low temperatures by NMR. Abnormally large shielding of one ortho hydrogen indicates that both the imino phenyl and heterocycle rings can engage in an edge-to-face interaction with the N-terminal phenyl moiety in the appropriate isomer. Some rotational barriers around the phenyl–imino and heterocycle–imino bonds were measured.
Descripción : Este es el post-print que se ha publicado de forma definitiva en: https://pubs.rsc.org/en/content/articlelanding/2017/ob/c6ob02618d#!divAbstract
URI : http://hdl.handle.net/10637/10592
Derechos: http://creativecommons.org/licenses/by-nc-nd/4.0/deed.es
ISSN : 1477-0520
1477-0539 (Electrónico)
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