Predicting reactive sites with quantum chemical topology: carbonyl additions in multicomponent reactions
| Autor: | Pablo Carpio-Martínez, David Ignacio Ramírez‐Palma, César R. García-Jacas, Fernando Cortés-Guzmán |
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| Rok vydání: | 2020 |
| Předmět: |
education.field_of_study
Quantitative structure–activity relationship 010405 organic chemistry Reaction step Chemistry Population General Physics and Astronomy 010402 general chemistry Topology 01 natural sciences 0104 chemical sciences Delocalized electron Organic reaction Electrophile Molecule Physical and Theoretical Chemistry education Equilibrium constant |
| Zdroj: | Physical chemistry chemical physics : PCCP. 22(17) |
| ISSN: | 1463-9084 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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