28627-67-0Relevant articles and documents
The nitro anomaly and Bronsted βnuc values in SN2 reactions on chlorine
Eliad, Linoam,Hoz, Shmaryahu
, p. 540 - 543 (2007/10/03)
The kinetics of chlorine transfer reactions between N-chlorosuccinimide (NCS) and four carbon nucleophiles (the conjugated bases of phenyldinitromethane, Meldrum's acid, phenylmalononitrile and phenylnitro-methane) in water were determined. A plot of log k for the SN2 reactions vs the pKa of the first three conjugated acids of the nucleophiles gave a straight line with a slope (βnuc) of 1.8. The data point for the mononitro derivative, phenylnitromethane, deviates negatively from the line by 6.7 log units. This deviation is typical of proton transfer reactions and was recently shown to occur also in SN2 reactions on bromine. Copyright
One-Electron Reduction Potential and Ring Opening of the Succinimidyl Radical in Water
Lind, Johan,Jonsson, Mats,Eriksen, Trygve E.,Merenyi, Gabor,Eberson, Lennart
, p. 1610 - 1614 (2007/10/02)
By means of pulse radiolysis in water, N-chlorosuccinimide (SCl) was reduced in a one-electron step to yield the succinimidyl radicals, S*, via the intermediacy of the radical anion, SCl*-.The rate of ring opening of S* was measured to be 8 x 104 s-1.By equilibrium with Cl2*-/2Cl-, the one-electron reduction potential of S* was determined to be 2.22 +/- 0.02 V vs NHE.From this value and other data, the N-H bond strength in succinimide was calculated to be 118 +/- 3 kcal/mol.
Nucleophilic Catalysis of the Hydrolysis of Phenyl Acetates by the Succinimide Anion in Aqueous Solution
Huffman, Robert W.
, p. 3687 - 3691 (2007/10/02)
Kinetic studies were conducted on the disapperance of some phenyl acetates in aqueous solutions buffered by succinimide/succinimide anion at 30 deg C.The most reasonable mechanistic scheme, compatible with the data, is that shown in Scheme I involving nuc