Reactions of nitroheteroarenes with carbanions: bridging aromatic, heteroaromatic, and vinylic electrophilicity was written by Seeliger, Florian;Blazej, Sylwia;Bernhardt, Sebastian;Makosza, Mieczyslaw;Mayr, Herbert. And the article was included in Chemistry – A European Journal in 2008.Formula: C4H5N3O2 This article mentions the following:
The relative rate constants for the vicarious nucleophilic substitution (VNS) of the anion of chloromethyl Ph sulfone (1–) with a variety of nitroheteroarenes, for example, nitropyridines, nitropyrroles, nitroimidazoles, 2-nitrothiophene, and 4-nitropyrazole, were determined by competition experiments Nitropyridines are approx. four orders of magnitude more reactive than nitrobenzene. Among the five-membered heterocycles 2-nitrothiophene is the most active followed by nitroimidazoles and 4-nitropyrazole. Nitropyrroles are the least electrophilic nitroheteroarenes with reactivities comparable to nitrobenzene. Quantum chem. calculated Me anion affinities (B3LYP/6-311G(d,p)//B3LYP/6-31G(d)) of the nitroarenes correlated only moderately with the partial relative rate constants The correlation of these activities with the LUMO energies of nitroarenes is even worse. By measuring the second-order rate constants of the addition of 1– to nitroarenes and to di-Et arylidenemalonates it was possible to link the electrophilic reactivities of nitroheteroarenes with the comprehensive electrophilicity scale based on the linear-free-energy-relation log k(20° C) = s(N + E). In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Formula: C4H5N3O2).
1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Formula: C4H5N3O2
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem