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Molecules 2017, 22(10), 1744; doi:10.3390/molecules22101744

A DFT Study of the Geometrical, Spectroscopical and Reactivity Properties of Diindolylmethane-Phenylboronic Acid Hybrids

Departamento de Ciencias Químicas, Facultad de Estudios Superiores Cuautitlán, Campo 1, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, Estado de Mexico C.P. 54740, Mexico
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Received: 13 September 2017 / Accepted: 12 October 2017 / Published: 17 October 2017
(This article belongs to the Section Theoretical Chemistry)
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Abstract

The structure of the ortho-, meta- and para- hybrid diindolylmethane-phenylboronic acids and their interactions were optimized with by a quantum chemical method, using density functional theory at the (DFT) level. Thus, infrared bands were assigned based on the scaled theoretical wavenumbers by correlating the respective experimental data of the molecules. In addition, the corresponding 1H-/13C-/11B-NMR experimental and theoretical chemical shifts were correlated. The target molecules showed a poor treatment of the OH shifts in the GIAO method due to the absence of explicit solvent effects in these calculations; therefore, they were explicitly considered with acetone molecules. Moreover, the electron density at the hydrogen bond critical point increased, generating stabilization energy, from weak to moderate or weak to strong, serving as an indicator of the strength of the hydrogen bond between the different intermolecular interactions. Finally, some properties related to the reactive behavior of the target molecules associated with their cytotoxic effects and metabolic pathways were also calculated. View Full-Text
Keywords: boronic acids; diindolylmethane; spectroscopy; DFT calculations; hydrogen bonds boronic acids; diindolylmethane; spectroscopy; DFT calculations; hydrogen bonds
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MDPI and ACS Style

Fragoso-Medina, A.J.; Escobedo-González, R.G.; Nicolás-Vázquez, M.I.; Arroyo-Razo, G.A.; Noguez-Córdova, M.O.; Miranda-Ruvalcaba, R. A DFT Study of the Geometrical, Spectroscopical and Reactivity Properties of Diindolylmethane-Phenylboronic Acid Hybrids. Molecules 2017, 22, 1744.

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