2026-04-13T08:40:53Zhttps://recercat.cat/oai/request

oai:recercat.cat:10256/113922024-06-18T13:49:34Zcom_2072_452955com_2072_2054col_2072_453073

Aromaticity and Magnetic Properties of 1-and 2-Indenones and Their Aza Derivatives Poater i Teixidor, Jordi Solà i Puig, Miquel Alkorta, Ibon Elguero, Jose Aromaticitat (Química) Aromaticity (Chemistry) Compostos heterocíclics -- Propietats magnètiques Heterocyclic compounds -- Magnetic properties Funcional de densitat, Teoria del Density functionals The almost unknown series of 1- and 2-indenones and their aza-derivatives have been analyzed with the aim of understanding the higher stability and aromaticity of the 1-one compared to the 2-one series. The effect of tetrafluorination of the six-membered ring on their relative stability and aromaticity and the corresponding 19F-19F spin-spin coupling constants (SSCC) have been analyzed for the compounds of these two series. Magnetic NICS and electronic PDI, FLU, and MCI aromaticity criteria, complemented by an energy decomposition analysis, allow the higher stability and aromaticity of 1-indenones compared with 2-indenones to be attributed to the p-component of the orbital interaction term. The reduced aromatic character of the 2-one series also provides an explanation for the F-19-F-19 SSCC observed in the tetrafluorinated 2-one compounds, which differ significantly from those of 1,2,3,4-tetrafluorobenzene Thanks are given to the Spanish Ministerio de Economia y Competitividad (MEC) (project numbers CTQ2012-13129-C02-02, CTQ2011-23156/BQU and CTQ2011-25086), the Comunidad Autonoma de Madrid (project MADRISOLAR2, ref. S2009/PPQ-1533) and the Generalitat de Catalunya (project numbers 2009SGR637 and 2009SGR528, Xarxa de Referencia en Quimica Teorica i Computacional, and ICREA Academia 2009 prize to M. S.) 2024-06-18T13:49:33Z 2024-06-18T13:49:33Z 2024-06-18T13:49:33Z info:eu-repo/date/embargoEnd/2026-01-01 info:eu-repo/date/embargoEnd/2026-01-01 2014 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://hdl.handle.net/10256/11392 info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201402509 info:eu-repo/semantics/altIdentifier/issn/1434-193X info:eu-repo/semantics/altIdentifier/eissn/1099-0690 info:eu-repo/grantAgreement/MICINN//CTQ2011-23156/ES/AVANCES EN CATALISIS Y AROMATICIDAD/ info:eu-repo/grantAgreement/MICINN//CTQ2011-25086/ES/MODELIZACION MULTIESCALAR EN (BIO)QUIMICA/ AGAUR/2009-2014/2009 SGR-637 AGAUR/2009-2014/2009 SGR-528 Tots els drets reservats info:eu-repo/semantics/embargoedAccess Wiley-VCH Verlag © European Journal of Organic Chemistry, 2014, vol. 24, p. 5370-5377 Articles publicats (D-Q)