Issue 17, 2020

Predicting reactive sites with quantum chemical topology: carbonyl additions in multicomponent reactions

Abstract

Quantum Chemical Topology (QCT) is a well established structural theoretical approach, but the development of its reactivity component is still a challenge. The hypothesis of this work is that the reactivity of an atom within a molecule is a function of its electronic population, its delocalization in the rest of the molecule, and the way it polarizes within an atomic domain. In this paper, we present a topological reactivity predictor for cabonyl additions, κ. It is a measure of the polarization of the electron density with the carbonyl functional group. κ is a model obtained from a QSAR procedure, using quantum-topological atomic descriptors and reported hydration equilibrium constants of carbonyl compounds. To validate the predictive capability of κ, we applied it to organic reactions, including a multicomponent reaction. κ was the only property that predicts the reactivity in each reaction step. The shape of κ can be interpreted as the change between two electrophilic states of a functional group, reactive and non-reactive.

Graphical abstract: Predicting reactive sites with quantum chemical topology: carbonyl additions in multicomponent reactions

Supplementary files

Article information

Article type
Paper
Submitted
17 jan 2020
Accepted
31 mar 2020
First published
31 mar 2020

Phys. Chem. Chem. Phys., 2020,22, 9283-9289

Predicting reactive sites with quantum chemical topology: carbonyl additions in multicomponent reactions

D. I. Ramírez-Palma, C. R. García-Jacas, P. Carpio-Martínez and F. Cortés-Guzmán, Phys. Chem. Chem. Phys., 2020, 22, 9283 DOI: 10.1039/D0CP00300J

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