Nucleophilic Aromatic Substitution Reactions Described by the Local Electron Attachment Energy was written by Stenlid, Joakim H.;Brinck, Tore. And the article was included in Journal of Organic Chemistry in 2017.Synthetic Route of C5F5N The following contents are mentioned in the article:
A local multiorbital electrophilicity descriptor, the local electron attachment energy [E(r)], is used to study the nucleophilic aromatic substitution reactions of SNAr and VNS (vicarious nucleophilic substitution). E(r) considers all virtual orbitals below the free electron limit and is determined on the mol. isodensity contour of 0.004 at units. Good (R2 = 0.83) to excellent (R2 = 0.98) correlations are found between descriptor values and exptl. reactivity data for six series of electron deficient arenes. These include homo- and heteroarenes, rings of five to six atoms, and a variety of fluorine, bromine, and hydride leaving groups. The solvent, temperature, and nucleophile are in addition varied across the series. The surface E(r) [ES(r)] provides reactivity predictions better than those of transition-state calculations for a concerted SNAr reaction with a bromine nucleofuge, gives correlations substantially stronger than those of LUMO energies, and is overall more reliable than the mol. electrostatic potential. Using ES(r), one can identify the various electrophilic sites within a mol. and correctly predict isomeric distributions. Since the calculations of ES(r) are computationally inexpensive, the descriptor offers fast but accurate reactivity predictions for the important nucleophilic aromatic substitution class of reactions. Applications in, e.g., drug discovery, synthesis, and toxicol. studies are envisaged. This study involved multiple reactions and reactants, such as 2,3,4,5,6-Perfluoropyridine (cas: 700-16-3Synthetic Route of C5F5N).
2,3,4,5,6-Perfluoropyridine (cas: 700-16-3) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Synthetic Route of C5F5N