Dissection of Nucleophilic and General Base Roles for the Reaction of Phosphate with p-Nitrophenyl Thiolacetate, p-Nitrophenyl Thiolformate, and Phenyl Thiolacetate

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7351-7357

  Gill, Manjinder S ^a   Neverov, Alexei A ^a   Brown, R S ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344475327     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970904b     Document Type: Article

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45. -3 M), 1 part of formic acid and 2 parts of hydroxamic acid are produced at pH 3.05. From the rate constants given in Table 6, at pH 3.05, 1 M phosphate, no hydroxylamine, about 2/3 of the reaction goes via the phosphate process. If all the reaction of phosphate is general base, then the amount of formic acid is 3 parts, and the amount of hydroxamic acid is 2 parts. If all the reaction is nucleophilic and the formyl phosphate reacts quantitatively with hydroxyl amine, then the amount of formic acid is 1 part and the amount of hydroxamic acid is 4 parts.
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