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Title

Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring

AuthorsPérez-Torralba, Marta; Claramunt, Rosa M.; García, M. Ángeles; López, Concepción; Torralba, M. Carmen; Torres, M. Rosario; Alkorta, Ibon ; Elguero, José
Keywordsbenzodiazepinones
DFT
GIAO calculations
inversion barriers
multinuclear NMR
tautomerism
X-ray structures
Issue Date2013
PublisherBeilstein-Institut für Literatur der Organischen Chemie
CitationBeilstein Journal of Organic Chemistry 9 : 2156–2167 (2013)
AbstractTwo novel tetrafluorinated 1,5-benzodiazepinones were synthesized and their X-ray structures determined. 6,7,8,9-Tetrafluoro-4- methyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one crystallizes in the monoclinic P21/c space group and 6,7,8,9-tetrafluoro-1,4- dimethyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one in the triclinic P−1 space group. Density functional theory studies at the B3LYP/6-311++G(d,p) level were carried out on these compounds and on four non-fluorinated derivatives, allowing to calculate geometries, tautomeric energies and ring-inversion barriers, that were compared with the experimental results obtained by static and dynamic NMR in solution and in solid state.
Publisher version (URL)http://dx.doi.org/10.3762/bjoc.9.253
URIhttp://hdl.handle.net/10261/89134
DOI10.3762/bjoc.9.253
Appears in Collections:(IQM) Artículos
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