“…The most important and best investigated representative of benziodoxoles is the commercially available 1-hydroxy-1,2-benziodoxole-3(1 H )-one ( 334 , R = H)the cyclic tautomer of 2-iodosylbenzoic acid. ,, Recently, Moss and co-workers reported the results of a structural reinvestigation of 4-alkyl-2-iodosylbenzoic acids, for which an open tautomeric form 333 was previously assigned by others. Contrary to the previous report, only the closed, iodoxolone form 334 of 4-alkyl-2-iodosobenzoic acid can be isolated; the previously assigned open (iodoso) form is actually 4-pentanoyl-2-iodobenzoic acid …”
Section: F Benziodoxolesmentioning
confidence: 99%
“…Contrary to the previous report, only the closed, iodoxolone form 334 of 4-alkyl-2-iodosobenzoic acid can be isolated; the previously assigned open (iodoso) form is actually 4-pentanoyl-2-iodobenzoic acid. 268 In the last 15 years 1-hydroxy-1,2-benziodoxole-3(1H)-one and its derivatives have attracted considerable research interest due to their excellent catalytic activity in the cleavage of toxic phosphates and reactive esters. An excellent, comprehensive review by Moss and Morales-Rojas on the phosphorolytic activity of o-iodosylcarboxylates and related nucleophiles appears in this issue of Chemical Reviews.…”
“…The most important and best investigated representative of benziodoxoles is the commercially available 1-hydroxy-1,2-benziodoxole-3(1 H )-one ( 334 , R = H)the cyclic tautomer of 2-iodosylbenzoic acid. ,, Recently, Moss and co-workers reported the results of a structural reinvestigation of 4-alkyl-2-iodosylbenzoic acids, for which an open tautomeric form 333 was previously assigned by others. Contrary to the previous report, only the closed, iodoxolone form 334 of 4-alkyl-2-iodosobenzoic acid can be isolated; the previously assigned open (iodoso) form is actually 4-pentanoyl-2-iodobenzoic acid …”
Section: F Benziodoxolesmentioning
confidence: 99%
“…Contrary to the previous report, only the closed, iodoxolone form 334 of 4-alkyl-2-iodosobenzoic acid can be isolated; the previously assigned open (iodoso) form is actually 4-pentanoyl-2-iodobenzoic acid. 268 In the last 15 years 1-hydroxy-1,2-benziodoxole-3(1H)-one and its derivatives have attracted considerable research interest due to their excellent catalytic activity in the cleavage of toxic phosphates and reactive esters. An excellent, comprehensive review by Moss and Morales-Rojas on the phosphorolytic activity of o-iodosylcarboxylates and related nucleophiles appears in this issue of Chemical Reviews.…”
“…The efficient chemical destruction of phosphonate nerve agents is an urgent and topical goal, , and the remediation of paraoxon or parathion contamination is similarly important. As first noted in 1983, o -iodosobenzoate ( 4 , IBA), in its preferred 1-oxido-1,2-benziodoxol-3( 1 H)-one form, is an effective catalyst for the rapid cleavage of “simulant” phosphates (e.g., p -nitrophenyl diphenyl phosphate, 5 , PNPDPP), and also for nerve agents such as sarin and soman . To solubilize both IBA and the target substrate in the mildly basic aqueous solutions required for efficient IBA catalysis, the reagent is generally deployed in micellar solutions of cetyltrimethylammonium chloride (CTA)Cl. , …”
Micellar cetyltrimethylammonium iodosobenzoate, (CTA)IBA, is highly reactive toward paraoxon (1) and parathion (2). In aqueous solution at pH 9, excess (CTA)IBA mediates their hydrolyses with kobs(max) ) 0.014 and 0.0030 s -1 , respectively, corresponding to half-lives of 50 s and 3.8 min. Comparisons with other phosphorolytic reagents suggest that (CTA)IBA merits serious consideration for the remediation of paraoxon or parathion contamination.
“…DMP was prepared by complete oxidation of 2iodobenzoic acid, followed by acetylation of 2-iodoxybenzoic acid (IBX). However, if the oxidation of iodobenzoic acid is incomplete, an intermediate, iodosobenzoic acid, will be produced, which can tautomerize between an open and a closed form (Moss et al, 1998). It is possible that the presence of an open form of iodosobenzoic acid facilitates the deprotonation of an -hydrogen and protonation of the ketone.…”
Key indicatorsSingle-crystal X-ray study T = 87 K Mean (C-C) = 0.002 Å R factor = 0.035 wR factor = 0.095 Data-to-parameter ratio = 12.7For details of how these key indicators were automatically derived from the article, see
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
