Cleavage of the Carbon—Sulfur Bond. Rates of Hydrolysis of Some Alkyl Acetates and the Corresponding Thiolacetates in Aqueous Acetone

1950 ◽  
Vol 72 (7) ◽  
pp. 3021-3025 ◽  
Author(s):  
Paul N. Rylander ◽  
D. Stanley Tarbell
Keyword(s):  
Aqueous Acetone ◽  
Alkyl Acetates ◽  
Hydrolysis Of ◽  
Sulfur Bond

scholarly journals Mechanism for the Hydrolysis of a Sulfur-Sulfur Bond Based on the Crystal Structure of the Thiosulfohydrolase SoxB

2009 ◽  
Vol 284 (32) ◽  
pp. 21707-21718 ◽  
Author(s):  
Véronique Sauvé ◽  
Pietro Roversi ◽  
Kirstin J. Leath ◽  
Elspeth F. Garman ◽  
Robin Antrobus ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrolysis Of ◽  
Sulfur Bond

Solvolysis of Sulphonyl Halides. I. The Hydrolysis of Aromatic Sulphonyl Chlorides in Aqueous Dioxan and Aqueous Acetone

1961 ◽  
Vol 14 (2) ◽  
pp. 190 ◽  
Author(s):  
FE Jenkins ◽  
AN Hambly
Keyword(s):  
Dielectric Constant ◽  
Reaction Rate ◽  
Acid Catalysis ◽  
Salt Effect ◽  
Aqueous Acetone ◽  
Low Dielectric Constant ◽  
Low Dielectric ◽  
Enthalpy Of Activation ◽  
Entropy Of Activation ◽  
Hydrolysis Of

The hydrolysis of benzene, p-toluene, p-bromobenzene, and p-nitrobenzene sulphonyl chlorides in 10-60 wt. % water-dioxan and water-acetone has been shown to follow an SN2 mechanism. The reaction does not show acid catalysis or any " salt " effect. Hammett?s equation does not describe fully the effects of substituents on the reaction rate. For solutions in which water has the same molarity, aqueous acetone gives lower rates than aqueous dioxan when the molarity of water is high but higher rates when the molarity of water is low. Change in the water content of the solvent produces only small changes in the enthalpy of activation except in solutions of low dielectric constant. The reduction in rate as solutions become less aqueous is mainly determined by the entropy of activation becoming more strongly negative.

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