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Issue 17, 2020
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Predicting reactive sites with quantum chemical topology: carbonyl additions in multicomponent reactions

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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

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Supplementary files

Article information


Submitted
17 Jan 2020
Accepted
31 Mar 2020
First published
31 Mar 2020

Phys. Chem. Chem. Phys., 2020,22, 9283-9289
Article type
Paper

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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