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Aromaticity of overcrowded nitroanilines.
Autorzy
Rok wydania
2012
Czasopismo
Journal of Physical Chemistry A
Numer woluminu
116
Strony
5629-5636
DOI
10.1021/jp212449m
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
For a series of 2,4,6-trinitroanilines substituted with bulky groups, the influence of intramolecular hydrogen bonds, electronic substituents effect, and steric hindrance on aromaticity of the molecules in crystals and their analogues optimized at the B3LYP/6-311++G** level were studied. The HOMA index was used as a measure of the aromaticity, while the parameter ΔP was a description of the distortion of the benzene ring from planarity. Conformation of the nonplanar ring in crystal and optimized structures was also described using the puckering parameters. A comparison of the data for crystal and optimized structures showed an important effect of the intermolecular interactions on aromaticity of the overcrowded nitroanilines. The packing effects were analyzed using the simplified PCM model of solvents. NBO analysis illustrated the changes of orbitals upon dearomatisation
Adres publiczny
http://dx.doi.org/10.1021/jp212449m
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