2532-15-2Relevant articles and documents
The effect of 4-halogenobenzoate ligands on luminescent and structural properties of lanthanide complexes: Experimental and theoretical approaches
Monteiro, Jorge H. S. K.,De Bettencourt-Dias, Ana,Mazali, Italo O.,Sigoli, Fernando A.
, p. 1883 - 1891 (2015/03/18)
The ligands 4-fluorobenzoate (4-fba), 4-chlorobenzoate (4-cba), 4-bromobenzoate (4-bba) and 4-iodobenzoate (4-iba) were chosen in order to synthesize europium(iii), gadolinium(iii) and terbium(iii) complexes and compare the effect of halogens on their phy
Effect of Distortion on the Hydrolytic Reactivity of Amides. 2. N-Pyramidalization: Decomposition of N-Benzoylaziridines in Aqueous Media
Slebocka-Tilk, H.,Brown, R. S.
, p. 805 - 808 (2007/10/02)
The decomposition of para-substituted N-benzoylaziridines (H, OCH3, NO2, Br) in buffered aqueous media is studied at 25 deg C as a function of pH in order to assess the effect of N-pyramidalization on the hydrolytic reactivity of the amide bond.Overall, the reaction shows three dominant terms: OH- and H2O attack on the neutral form and H2O attack on the protonated form of the amide.In base, the exclusive reaction is rate-limiting and irreversible attack of OH- on the C=O unit leading to normal hydrolytic products.This is shown by the first-order dependence on -> from pH 8 to 14 of the hydrolysis rate and by the fact that ca. 50percent 18O-enriched amide recovered from the hydrolysis medium as a function of time shows no 18O loss.Relative to N,N-dimethylbenzamide (kOH-25 deg C = 6.0 * 10-6 M-1 s-1), N-benzoylaziridine is ca. 200 000-fold more susceptible to OH- attack (kOH-25 deg C = 1.1 M-1 s-1).The kOH- terms follow a ?ρ relationship with ρ = 1.68.In acid, the products are not the expected hydrolytic ones of benzoic acid and aziridine.Rather, exclusive ring opening occurs to give p-X-C6H4C(=O)NHCH2CH2OX.In acetate buffers, product analysis by 1H NMR indicates that the ring-opened material consists of alcohol and acetate (X = H and C(=O)CH3).