Journal
MOLECULES
Volume 25, Issue 5, Pages -Publisher
MDPI
DOI: 10.3390/molecules25051085
Keywords
[3+2] cycloadditions; nitrilimines; nitrile oxides; chemoselectivity; molecular electron density theory; molecular mechanisms
Funding
- European Union [84618]
- Ministry of Economy and Competitiveness (MINECO) of the Spanish Government [CTQ2016-78669-P]
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The [3+2] cycloaddition (32CA) reactions of diphenyl nitrilimine and phenyl nitrile oxide with (R)-carvone have been studied within the Molecular Electron Density Theory (MEDT). Electron localisation function (ELF) analysis of these three-atom-components (TACs) permits its characterisation as carbenoid and zwitterionic TACs, thus having a different reactivity. The analysis of the conceptual Density Functional Theory (DFT) indices accounts for the very low polar character of these 32CA reactions, while analysis of the DFT energies accounts for the opposite chemoselectivity experimentally observed. Topological analysis of the ELF along the single bond formation makes it possible to characterise the mechanisms of these 32CA reactions as cb- and zw-type. The present MEDT study supports the proposed classification of 32CA reactions into pdr-, pmr-, cb- and zw-type, thus asserting MEDT as the theory able to explain chemical reactivity in Organic Chemistry.
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