110827-84-4Relevant articles and documents
Solution and Solid State Study on the Recognition of Hydroxyaromatic Aldoximes by Nitrogen Containing Compounds
Tarai, Arup,Baruah, Jubaraj B.
, p. 126 - 135 (2016)
Structural aspects and fluorescence behaviors of a series of cocrystals of hydroxyaromatic aldoximes, namely, 2(H2NAP)·(4,4′-bipyridine), 2(H2NAP)·(HMTA), H2NAP·caffeine, and (H3OHPA)·theophylline·2H2
A study on fluoride detection and assembly of hydroxyaromatic aldoximes caused by tetrabutylammonium fluoride
Tarai, Arup,Baruah, Jubaraj B.
, p. 2301 - 2309 (2015)
Tetrabutylammonium fluoride (TBAF) forms cocrystal H2NAP·TBAF with 2-hydroxynaphthaldoxime (H2NAP) or cocrystal 2(H3OHPA)·TBAF with 2,3-dihydroxyphenylaldoxime (H3OHPA), whereas a similar reaction with 2,4-dihydroxyphenylaldoxime (H3PHPA) forms tetrabutylammonium (TBA) salt TBA(H2.5PHPA)2. Formation of these cocrystals or salts is accompanied by a color change which enables the detection of fluoride ions. Cocrystal H2NAP·TBAF has a layered structure formed by hydrogen bonds between the fluoride ions and parent oxime molecules; the tetrabutylammonium cations are held in between layers of anionic assemblies. On the other hand, cocrystal 2(H3OHPA)·TBAF has a grid-like architecture constructed from hydrogen bonds between the parent oxime molecules and fluoride ions. TBA cations are encapsulated within the grids. It is shown that salt TBA(H2.5PHPA)2 forms anionic assemblies to encapsulate tetrabutylammonium cations which are devoid of fluoride ions. By interactions of the tetrabutylammonium fluoride ions with H3PHPA molecules, an anionic assembly is formed by the sharing of protons, which possesses a grid-like structure. The formation of such an assembly causes color change which enables one to detect fluoride ions by visual means. This journal is
Reactivity and mechanism of α-nucleophile scaffolds as catalytic organophosphate scavengers
Wong, Pamela T.,Bhattacharjee, Somnath,Cannon, Jayme,Tang, Shengzhuang,Yang, Kelly,Bowden, Sierra,Varnau, Victoria,O'Konek, Jessica J.,Choi, Seok Ki
supporting information, p. 3951 - 3963 (2019/04/30)
Despite their unique benefits imparted by their structure and reactivity, certain α-nucleophile molecules remain underexplored as chemical inactivators for the topical decontamination of reactive organophosphates (OPs). Here, we present a library of thirty α-nucleophile scaffolds, each designed with either a pyridinium aldoxime (PAM) or hydroxamic acid (HA) α-nucleophile core tethered to a polar or charged scaffold for optimized physicochemical properties and reactivity. These library compounds were screened for their abilities to catalyze the hydrolysis of a model OP, paraoxon (POX), in kinetic assays. These screening experiments led to the identification of multiple lead compounds with the ability to inactivate POX two- to four-times more rapidly than Dekon 139 - the active ingredient currently used for skin decontamination of OPs. Our mechanistic studies, performed under variable pH and temperature conditions suggested that the differences in the reactivity and activation energy of these compounds are fundamentally attributable to the core nucleophilicity and pKa. Following their screening and mechanistic studies, select lead compounds were further evaluated and demonstrated greater efficacy than Dekon 139 in the topical decontamination of POX in an ex vivo porcine skin model. In addition to OP reactivity, several compounds in the PAM class displayed a dual mode of activity, as they retained the ability to reactivate POX-inhibited acetylcholine esterase (AChE). In summary, this report describes a rationale for the hydrophilic scaffold design of α-nucleophiles, and it offers advanced insights into their chemical reactivity, mechanism, and practical utility as OP decontaminants.
