41577-89-3

Upstream product

• 88-88-0 2,4,6-trinitrochlorobenzene 
• 75-08-1 ethanethiol 
• 55526-39-1 pyrrolidinium 
• 17523-59-0 piperidinium cation 
• 16999-97-6 N-butylammonium cation 
• 129804-47-3 C₈H₈N₃O₇S^(1-) 

Downstream Products

• 17523-59-0 piperidinium cation 
• 41577-90-6 1,4-Bis-aethylthio-2,6-dinitrobenzol 
• 14798-26-6 picrate anion 
• 76671-54-0 5-Ethoxy-2-ethylsulfanyl-1,3-dinitro-benzene 
• 129804-47-3 C₈H₈N₃O₇S^(1-) 
• 88-89-1 2,4,6-Trinitrophenol 
• 32902-85-5 N-butyl-2,4,6-trinitroaniline 
• 75-08-1 ethanethiol 
• 16999-97-6 N-butylammonium cation 
• 77379-02-3 2,4,6-trinitro-1-pyrrolidinobenzene 

Relevant academic research and scientific papers

Kinetic and equilibrium studies of σ-adduct formation and substitution in the reactions of sulphite ions with some alkyl and aryl ethers and thioethers

Kinetic and equilibrium results are reported for the reactions of sulphite with the ethyl and phenyl ethers of 2,4,6-trinitrophenol and 2,4,6-trinitrothiophenol in 80/20 (v/v) water/DMSO. In each case 1:1 and 1:2 adducts are observed by reaction of sulphite at one or two unsubstituted ring positions respectively. In the case of the ethyl derivatives these adducts are long-lived; however, the phenyl derivatives rapidly yield 2,4,6-trinitrobenzene-sulphonate, the substitution product. This difference is attributed to a change in the nature of the rate-determining step, from nucleophilic attack with the phenyl derivatives to leaving group departure with the alkyl derivatives.

Kinetic and Equilibrium Studies of ?-Adduct Formation and Nucleophilic Substitution in the Reactions of Hydroxide Ions with 2,4,6-Trinitrophenyl Sulfides and Ethers

Kinetic and equlibrium data are reported for reaction of hydroxide ions in 20/80 DMSO/water (v/v) with a series of 4'-substituted phenyl 2,4,6-trinitrophenyl sulfides, 1, and with ethyl thiopicrate, 2, ethyl picrate, 3, phenyl picrate, 4, and 1,3,5-trinitrobenzene, 5.In each case a rapid reaction is observed involving reversible hydroxide addition at an unsubstituted ring-position.In the case of 1-4 this is followed by slower, irreversible attack at the 1-position leading to the formation of picric acid.The Hammett ρ value for equilibrium addition of hydroxide to the 3-position of 1 is 0.98, and the ρ value for rate constants for attack at the 1-position is 0.62.The results are discussed in terms of the electronic and steric effects of the 1-substituents.Comparison of 1-5 indicates that changing from an OR to SR group introduces additional steric crowding.However for the reactions studied changing from R = Et to R = Ph has little steric consequence.

Kinetic and Equilibrium Studies of ?-Adduct Formation and Nucleophilic Substitution in the Reactions of Ethyl Thiopicrate with Aliphatic Amines in Dimethyl Sulfoxide

Kinetic and equilibrium results are reported for the reaction of ethyl thiopicrate with butylamine, pyrrolidine and piperidine in dimethyl sulfoxide.The most rapid reaction involves attack at the unsubstituted 3-position to give anionic ?-adducts.The rate-limiting step in this process changes from nucleophilic attack by amine with butylamine to proton transfer from the zwitterionic intermediate with piperidine; pyrrolidine shows intermediate behaviour.Attack by amine at the 1-position results in displacement of the ethylthio group, although intermediates are notobserved during this process.It is suggested that base catalysis observed in the reaction with pyrrolidine may result from rate-limiting proton transfer from the zwitterionic intermediate. 1H NMR measurements using 0.1 mol dm-3 solutions of substrate show that the displaced ethanethiolate ion may attack ring-carbon atoms of either unreacted substrate or substitution products.