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Beilstein-Institut, Beilstein Journal of Organic Chemistry, (9), p. 2156-2167, 2013

DOI: 10.3762/bjoc.9.253

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

Journal article published in 2013 by Marta Pérez-Torralba, Rosa M. Claramunt, M. Ángeles García, M. Angeles García, M. Carmen Torralba, Concepción López, M. Carmen Torralba, M. Rosario Torres, Ibon Alkorta ORCID, José Elguero
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

Two 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.