Halogen Interactions in Halogenated Oxindoles: Crystallographic and Computational Investigations of Intermolecular Interactions

Abstract

X-ray structural determinations and computational studies were used to investigate halogen interactions in two halogenated oxindoles. Comparative analyses of the interaction energy and the interaction properties were carried out for Br···Br, C-H···Br, C-H···O and N-H···O interactions. Employing Møller–Plesset second-order perturbation theory (MP2) and density functional theory (DFT), the basis set superposition error (BSSE) corrected interaction energy (Eint(BSSE)) was determined using a supramolecular approach. The Eint(BSSE) results were compared with interaction energies obtained by Quantum Theory of Atoms in Molecules (QTAIM)-based methods. Reduced Density Gradient (RDG), QTAIM and Natural bond orbital (NBO) calculations provided insight into possible pathways for the intermolecular interactions examined. Comparative analysis employing the electron density at the bond critical points (BCP) and molecular electrostatic potential (MEP) showed that the interaction energies and the relative orientations of the monomers in the dimers may in part be understood in light of charge redistribution in these two compounds.

Theoretical study of the interaction of fullerenes with the emerging contaminant carbamazepine for detection in aqueous environments

“…Because ωB97XD is reported to deliver good interaction energies between system where non-covalent interactions are important 37 , 38 , 72 , 74 , 75 , we will henceforth discuss the interaction energies between CBZ and C 59 X relying on calculations performed at the ωB97XD/6-31G(d) level of theory. In Table 2 and Fig.…”

“…In order to understand this exception, the charge distribution, along the hexanes and pentane face surrounding the heteroatoms, was evaluated. It is well known that dominant partial charges, either positive or negative, accumulated on specific parts of interacting molecules have important influence for effective interaction 74 , 77 , 78 . Bearing it in mind, the sum of the ESP charges in the two hexanes faces and in the pentane face around the doping atoms was taken into account (See Fig.…”

(Ro)vibrational Spectroscopic Constants, Lifetime and QTAIM Evaluation of Fullerene Dimers Stability

“…In the QTAIM approach, every topological idiosyncrasy of ρ ( r ) (whether a maximum, minimum, or saddle point) is associated with a specific point in space, referred to as the critical point, where the gradient of ρ ( r ) vanishes [ 51 ]. Currently, the QTAIM approach has found large applicability in the study of many electronic properties; specifically, it has been employed in the study of weak interacting systems [ 10 , 11 , 54 ]. The topological characterization of the NCIs was studied in the case of fullerene dimers.…”