Structure and stability of aminoiminomethanesulfonic acid

Макаров, С. В.; Mundoma, Claudius; Penn, John H.; Petersen, Jeffrey L.; Svarovsky, Serge A.; Simoyi, Reuben H.

doi:10.1016/s0020-1693(98)00392-2

Cited by 33 publications

(68 citation statements)

References 31 publications

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“…10 -6 s -1 under the experimental conditions studied; this value is in very good agreement with the value of 2.5 ϫ 10 -6 s -1 found by Makarov and co-workers. [47] The inclusion of Equation (1) in the kinetic model with a fixed rate coefficient of 2.5 ϫ 10 -6 s -1 does not change the average deviation, from which we concluded that this process may only have a very minor contribution to the kinetics of the title reaction. Qualitatively, the initial drop in the absorbance can be explained by the formation of hydrogen sulfite ions from the slow aging of TTO solution to efficiently remove ClO 2 through the rapid hydrogen sulfitechlorine dioxide reaction already included in the proposed kinetic model.…”

Section: Discussionmentioning

confidence: 70%

Mechanism Involving Hydrogen Sulfite Ions, Chlorite Ions, and Hypochlorous Acid as Key Intermediates of the Autocatalytic Chlorine Dioxide–Thiourea Dioxide Reaction

Horváth

Duan

et al. 2015

Eur J Inorg Chem

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The kinetics of the chlorine dioxide–thiourea dioxide reaction was investigated by monitoring absorbance–time profiles at λ = 360 nm. Under acidic conditions, the primary carbon‐containing product is cyanamide, not urea as considered previously for many oxidation reactions of thiourea dioxide. Increase of the rate of the reaction by an increase of pH can be readily explained by the slow pH‐dependent formation of a more reactive form of thiourea dioxide (TDO) that is produced steadily and unavoidably as the stock TDO solution ages. We have also found that the absorbance–time profiles of the chlorine dioxide–TDO reaction are sigmoidal with excess TDO. The addition of methionine as a hypochlorous acid scavenging agent inhibits the reaction significantly, whereas the addition of chlorite ions and trace amounts of hydrogen sulfite ions accelerates the decay of chlorine dioxide. On the basis of these experiments, a sixteen‐step kinetic model involving hypochlorous acid, chlorite ions, and hydrogen sulfite ions as key intermediates that provide an autocatalytic cycle is proposed to account for the overall kinetic behavior observed, including the slow rearrangement of TDO.

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Section: Discussionmentioning

confidence: 70%

Mechanism Involving Hydrogen Sulfite Ions, Chlorite Ions, and Hypochlorous Acid as Key Intermediates of the Autocatalytic Chlorine Dioxide–Thiourea Dioxide Reaction

Horváth

Duan

et al. 2015

Eur J Inorg Chem

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“…Detailed data on 1 H, 13 C, and 17 O NMR spectra of thiourea oxides can also be found in several reports 11a. 26b, 28–31…”

Section: Synthesis and Structurementioning

confidence: 90%

“…The decisive role of hydrogen bonds may partly be related to the fact that tetramethylthiourea dioxide has not been yet prepared in solid state. [13] Hydrogen bonds strongly influence the density of thi- www.chemeurj.org ourea oxides as well: the density of N,N'-dimethylthiourea dioxide (1.496 g cm À3 ) [44] is much lower than that recorded for thiourea di-(1.70 g cm À3 ) [42] and trioxide (1.948 g cm À3 ), [28] which is probably a consequence of the absence of extensive hydrogen bonding in the first compound. As mentioned above, many researchers and even suppliers generally use the term "aminoiminomethanesulfinic acid" (AIMSA), instead of thiourea dioxide.…”

Section: Synthesis and Structurementioning

confidence: 98%

“…The corresponding ureas are the only nitrogen‐containing products of thiourea, N ‐methylthiourea, and N,N′ ‐dimethylthiourea dioxides in strongly alkaline solutions 50. In less alkaline media (pH 10) cyanamides as well as ammonia are also formed22b (ammonia is formed when thiourea trioxide decomposes in weakly acidic media,28 as well). Under similar conditions (pH around 10), thiourea trioxide gives melamine as well as cyanoguanidine 22b.…”

Section: Stability and Reactivitymentioning

confidence: 99%

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Recent Developments in the Chemistry of Thiourea Oxides

Макаров

Horváth

Silaghi-Dumitrescu

et al. 2014

Chemistry A European J

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Thiourea dioxide is one of the best known, important, and stable products of thiourea oxidation. This compound has long been considered as an effective reducing agent for many years. Traditional areas of its application include the textile and paper industries. In recent years, however, thiourea dioxides and trioxides have been widely used in new fields including organocatalytic, polymerization, and phase-transfer reactions; reduction of graphene and graphite oxides; bitumen modifications; synthesis of guanidines and their derivatives; and studying nonlinear dynamical phenomena in chemical kinetics. The review gives a detailed survey of the latest developments and main trends in the chemistry and application of thiourea mon-, di-, and trioxides.

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“…For background to phosphonic acid and metal phosphonate compounds, see: Ayyappan et al (2001); Clearfield (1998); Haga et al (2007); Vivani et al (2008); Bao et al (2007); Cave et al (2006); Cao et al (1992); Ma et al (2006Ma et al ( , 2008. For a related structure, see Makarov et al (1999).…”

Section: Related Literaturementioning

confidence: 99%

[Amino(iminio)methyl]phosphonate

et al. 2010

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The title compound, CH5N2O3P, exists as a zwitterion. The N atom of the imino group is protonated and the phosphonic acid group is deprotonated. The molecular geometry about the central C atom of this zwitterionic species was found to be strictly planar with the sum of the three angles about C being precisely 360°. In the crystal, the molecules are interlinked by O—H⋯O and N—H⋯O hydrogen-bonding interactions, forming a three-dimensional supramolecular network structure.

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Structure and stability of aminoiminomethanesulfonic acid

Cited by 33 publications

References 31 publications

Mechanism Involving Hydrogen Sulfite Ions, Chlorite Ions, and Hypochlorous Acid as Key Intermediates of the Autocatalytic Chlorine Dioxide–Thiourea Dioxide Reaction

Mechanism Involving Hydrogen Sulfite Ions, Chlorite Ions, and Hypochlorous Acid as Key Intermediates of the Autocatalytic Chlorine Dioxide–Thiourea Dioxide Reaction

Recent Developments in the Chemistry of Thiourea Oxides

[Amino(iminio)methyl]phosphonate

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