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A General Buffer‐Acid‐Catalyzed C−O Cleavage Reaction in the Hydrolysis of Phenyl N ‐(Phenoxycarbonyl)sulfamate Ester
Author(s) -
Blans Patrick,
Vigroux Alain
Publication year - 1999
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19990503)5:5<1526::aid-chem1526>3.0.co;2-l
Subject(s) - chemistry , cleavage (geology) , catalysis , hydrolysis , bond cleavage , phosphate buffered saline , buffer (optical fiber) , sulfate , aqueous solution , phosphate , fission , medicinal chemistry , organic chemistry , chromatography , telecommunications , fracture (geology) , physics , geotechnical engineering , quantum mechanics , neutron , engineering , computer science
Why do the nitrogen anions of N ‐(oxycarbonyl)sulfamate esters (illustrated) experience buffer‐acid catalysis for leaving‐group expulsion by C−O bond cleavage and not by S−O bond fission? Resolution of this question may have important biological implications with conclusions concerning the aqueous decompositions of phosphate and sulfate monoesters in acid.