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

• Published in: Molecules (Basel, Switzerland) Vol. 22; no. 10; p. 1744
• Main Authors: Fragoso-Medina, Amira Jalil, Escobedo-González, René Gerardo, Nicolás-Vázquez, María Inés, Arroyo-Razo, Gabriel Arturo, Noguez-Córdova, María Olivia, Miranda-Ruvalcaba, René
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 17-10-2017; MDPI
• Subjects: Acetone; Acids; Band theory; boronic acids; Boronic Acids - chemistry; Boronic Acids - metabolism; Critical point; Cytotoxicity; Density functional theory; DFT calculations; diindolylmethane; Electron density; Hybrids; Hydrogen Bonding; Hydrogen bonds; Indoles - chemistry; Indoles - metabolism; Magnetic Resonance Spectroscopy; Metabolic Detoxication, Phase I; Metabolic Networks and Pathways; Metabolic pathways; Models, Molecular; Molecular Structure; NMR; Nuclear magnetic resonance; Quantum Theory; spectroscopy; Spectroscopy, Fourier Transform Infrared; Spectrum Analysis - methods; diindolylmethane; spectroscopy; hydrogen bonds; DFT calculations; boronic acids
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules22101744

The structure of the
-,
- and
- 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-/
C-/
B-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.