4346-49-0Relevant academic research and scientific papers
The synthesis, conformation and hydrolytic stability of an: N, S -bridging thiophosphoramidate analogue of thymidylyl-3′,5′-thymidine
Conway, Louis P.,Mikkola, Satu,O'Donoghue, Annmarie C.,Hodgson, David R. W.
, p. 7361 - 7367 (2016)
A 3′-N,5′-S-bridging thiophosphoramidate analogue of thymidylyl-3′,5′-thymidine was synthesised under aqueous conditions. 1H NMR conformational measurements show that the 3′-N-substituted deoxyribose ring is biased towards the 'north', RNA-like conformation. Rate constants for hydrolysis of the analogue were measured at 90 °C in the pH range 1.3-10.9. The pH-log kobs profile displays a pH-independent region between approximately pH 7 and 10 (t1/2 ～13 days). Under acidic conditions, kobs displays a first order dependence on [H3O+].
Selective introduction of sulfo groups into aromatic nitro compounds
Dutov, Mikhail D.,Serushkina, Olga V.,Shevelev, Svyatoslav A.,Lyssenko
, p. 347 - 348 (2008/04/05)
A new reaction has been found, viz. oxidative destruction of nitro-substituted sulfones ArSO2CH2CO2Me to give sulfonic acids ArSO3H on treatment with 70% HNO3; in addition, di(arylsulfonyl)furoxans ar
New procedure for nucleophilic sulfonation of aromatic nitro compounds: Destructive oxidation of S-arylthioglycolic acids esters
Dutov,Serushkina,Shevelev
, p. 1167 - 1169 (2008/03/11)
A new reaction was discovered: oxidative destruction of sulfides of ArSCH2CO2Me type to sulfonic acids ArSO3H effected by 70% HNO3. This reaction was used to introduce an SO 3H group instead of aromat
Nucleophilicity towards a Saturated Carbon Atom: Rate Constants for the Aminolysis of Methyl 4-Nitrobenzenesulfonate in Aqueous Solution. A Comparison of the n and N+ Parameters for Amine Nucleophilicity
Bunting, John W.,Mason, Jacqueline M.,Heo, Christina K. M.
, p. 2291 - 2300 (2007/10/02)
Second-order rate constants (kNu) have been measured in aqueous solution (I = 0.1 mol dm-3, 25 deg C) for the SN2 reactions of methyl 4-nitrobenzenesulfonate with ammonia, 41 primary amines, 20 secondary amines,29 tertiary amines and 7-anionic nucleophiles.For the aminolysis reactions, Broensted-type correlations of nucleophilicity with basicity require the classification of all amines in terms of strictly defined structural classes with βnuc in the range 0.15-0.39.Swain-Scott plots indicate that simple amines, water and other light-atom nucleophiles (hydroxide, azide and cyanide anions) are five times more reactive than heavy-atom nucleophiles (thiosulfate, thocyanate, iodide and bromide ions).For amine nucleophiles there is a close linear correlation (of slope 0.44 , and including both primary and secondary amines) between log kNu for the aminolysis of methyl 4-nitrobenzenesulfonate and log kNu for amine addition to the 1-methyl-4-vinylpyridinium cation.This correlation demonstrates a close linear relationship between the Swain-Scott n parameter and Ritchie's N+ parameter for amine nucleophiles in aqueous solution (N+ = 2.1n - 4.3).
