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Bonding in tropolone, 2-aminotropone, and aminotroponimine: No evidence of resonance-assisted hydrogen-bond effects

AuthorsSanz, P.; Mó, O.; Yáñez, M.; Elguero, José CSIC ORCID
Issue Date2008
PublisherJohn Wiley & Sons
CitationChemistry - A European Journal 14: 4225- 4232 (2008)
AbstractThe 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.
Publisher version (URL)http://dx.doi.org/10.1002/chem.200701827
Identifiersdoi: 10.1002/chem.200701827
issn: 0947-6539
e-issn: 1521-3765
Appears in Collections:(IQM) Artículos
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