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Título: | Bonding in tropolone, 2-aminotropone, and aminotroponimine: No evidence of resonance-assisted hydrogen-bond effects |
Autor: | Sanz, P.; Mó, Otilia CSIC ORCID; Yáñez, M.; Elguero, José CSIC ORCID | Fecha de publicación: | 2008 | Editor: | John Wiley & Sons | Citación: | Chemistry - A European Journal 14: 4225- 4232 (2008) | Resumen: | The properties of the intramolecular hydrogen bond (IMHB) in tropolone, aminotropone, and aminotroponimine have been compared with those in the corresponding saturated analogues at the B3LYP/6-311+G-(3df,2p)//B3LYP/6- 311+G(d,p) level of theory. In general, all those compounds in which the seven-membered ring is unsaturated exhibit a stronger IMHB than their saturated counterparts. Nevertheless, this enhanced strength is not primarily due to resonance-assisted hydrogen-bond effects, but to the much higher intrinsic basicity and acidity of the hydrogen-bond acceptor and donor groups, respectively, in the unsaturated compounds. These acidity and basicity enhancements have a double origin: 1) the unsaturated nature of the moiety to which the hydrogen-bond donor and acceptor are attached and 2) the cyclic nature of the compounds under scrutiny. As has been found for hydroxymethylene and aminomethylene cyclobutanones, and cyclobutenones and their nitrogen-containing analogues, the IMHB strength follows the [donor, acceptor] trend: [OH, C=NH]> [OH, C=O]> [NH2, C=NH] > [NH2, C=O] and fulfills a Steiner-Limbach correlation similar to that followed by intermolecular hydrogen bonds. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA. | Versión del editor: | http://dx.doi.org/10.1002/chem.200701827 | URI: | http://hdl.handle.net/10261/66715 | DOI: | 10.1002/chem.200701827 | Identificadores: | doi: 10.1002/chem.200701827 issn: 0947-6539 e-issn: 1521-3765 |
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