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Aromaticity and Magnetic Properties of 1‐ and 2‐Indenones and Their Aza Derivatives
Author(s) -
Poater Jordi,
Solà Miquel,
Alkorta Ibon,
Elguero José
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402509
Subject(s) - aromaticity , chemistry , ring (chemistry) , computational chemistry , decomposition , series (stratigraphy) , stereochemistry , molecule , organic chemistry , paleontology , biology
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 19 F– 19 F 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 π‐component of the orbital interaction term. The reduced aromatic character of the 2‐one series also provides an explanation for the 19 F– 19 F SSCC observed in the tetrafluorinated 2‐one compounds, which differ significantly from those of 1,2,3,4‐tetrafluorobenzene.