Sulfamic acid and its N-substituted derivatives

Benson, G. Anthony; Spillane, William J.

doi:10.1021/cr60324a002

Cited by 117 publications

(69 citation statements)

References 107 publications

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“…Thioguanine inhibited PnP sulfation competitively with a K i of 70 Ϯ 10 M. The pK a of thioguanine is low, 3.7 (46). Sulfonated, low pK a primary amines are typically unstable toward hydrolysis (47). If the sulfonated product were hydrolyzed quickly relative to its formation, product will not be observed; instead, thioguanine will appear to stimulate production of 35 SO 4 from 35 PAPS.…”

Section: Resultsmentioning

confidence: 99%

High Accuracy in Silico Sulfotransferase Models

Cook

Wang

Falany

et al. 2013

Journal of Biological Chemistry

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Background: Human sulfotransferases (SULTs) regulate the bioactivities of hundreds of compounds in vivo. Results:The in silico models of SULTs developed here proved remarkably accurate in identifying SULT substrates in a 1,455-compound library containing all FDA-approved drugs. Conclusion: Highly accurate in silico SULT models are now available. Significance: The elision of mechanism and modeling can produce remarkably accurate in silico tools for the study of biology.

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Section: Resultsmentioning

confidence: 99%

High Accuracy in Silico Sulfotransferase Models

Cook

Wang

Falany

et al. 2013

Journal of Biological Chemistry

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“…The contribution of these MO's, together with the fact that the centroid of charge of the S-0 a bond is very close to the oxygen atom, yields a considerably polar S-0 linkage, which is reflected by the atomic populations and by the high dipole moment of the different conformers of sulfamide. Another consequence of the strong depopulation of sulfur is that the nitrogen atoms must satisfy their electronegativity, withdrawing a considerable amount of charge from the amino protons, which explains the acidic character of sulfamide as compared, for instance, with ammonia (1,36,37). The strong withdrawing effect of the oxygens of the SO2 group may be also responsible for the low rotational barrier observed (26) in 4,4-dioxy-4-thia-1-acetyl-l,4-dihydropyridine.…”

Section: S -0 Bonding Characteristicsmentioning

confidence: 99%

A molecular orbital study of the conformation (inversion and rotational barriers) and electronic properties of sulfamide

Mó¹,

Paz²,

Yáñez³

et al. 1989

Can. J. Chem.

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Chem. 67, 2227 (1989).Ab initio calculations have been used to study the conformational potential surface of sulfamide, by considering the S-N bond rotations and the nitrogen inversion processes. The lowest energy conformation (b) is found for a cis-trans arrangement of the amino groups, although conformations with cis-cis (a), trans-trans (c), and near staggered (c') arrangements lie close in energy. Nitrogen inversion barriers are very low, and consequently one may expect forms b and c' to be the only ones present in the gas phase. Conformer a is very polar, its dipole moment being twice that of b, so it may be favored in condensed media or in polar-solvent solutions. The relative stability of the different isomers is governed by interactions between the amino protons and between the nitrogen lone pairs. Our results show that d-n backbonding, involving the d orbitals on sulfur, is responsible for the multiple bond character of the S-0 linkage, but is very small in the S-N interactions. The role of the sulfur d-orbital exponent, when a 6-31G* basis is used, is analyzed on a series of model compounds containing S", STV, and SV1. Although the inclusion of d functions on sulfur is crucial to describing correctly the bonding in sulfamide, the results obtained do not change appreciably if a second set of d functions is centered on sulfur. Nevertheless, only when polarization functions are also included for first-row atoms is the description of the system reliable.Key

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“…Recently, it has been reported that the KNH 2 SO 3 crystal also undergoes another phase transition at 350 K and becomes an ionic conductor at high temperature, and the CsNH 2 SO 3 crystal has a structural phase transition from monoclinic P2 1 /c to orthorhombic Pnma at 330 K (Varughese et al, 2010;Kumar et al, 2011;Fukami et al, 2011). The sulfamic acid and its derivatives are interested in industrial applications, and are widely used in a variety of applications such as a fireproofing agent, an anticorrosive agent, a cross-linking agent for polymers, and a cleaning agent for air, etc (Benson & Spillane, 1980). The NH 4 NH 2 SO 3 and C(NH 2 ) 3 NH 2 SO 3 compounds of the ANH 2 SO 3 -type have good abilities as fire retardant (Benson & Spillane, 1980 (Wickleder, 2005).…”

Section: Introductionmentioning

confidence: 99%

“…The sulfamic acid and its derivatives are interested in industrial applications, and are widely used in a variety of applications such as a fireproofing agent, an anticorrosive agent, a cross-linking agent for polymers, and a cleaning agent for air, etc (Benson & Spillane, 1980). The NH 4 NH 2 SO 3 and C(NH 2 ) 3 NH 2 SO 3 compounds of the ANH 2 SO 3 -type have good abilities as fire retardant (Benson & Spillane, 1980 (Wickleder, 2005). The crystal has an orthorhombic structure with space group Pnma, and consists of chains of OH -centered [Pb 2+ ] 3 triangles and four types of PbO(N) x (x=8-10) polyhedra (Wickleder, 2005).…”

Section: Introductionmentioning

confidence: 99%

Crystal Growth and Structure of a New PbHNSO3 Crystal

Fukami¹,

Seino²,

Nakasone³

et al. 2013

IJC

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A new type of PbHNSO 3 crystal has been grown by a gel method using agar-agar gel. TG-DTA and X-ray diffraction measurements have been performed on single crystal samples of PbHNSO 3 . It is found that the thermal decomposition of the compound starts at about 960 K. The space group (orthorhombic Pnma) and structural parameters are determined at room temperature with unit cell dimensions: a=8.4690(6), b=5.3934(4) and c=6.9530(4) Å. The crystal structure is found to consist of NSO 3 pseudo-tetrahedra, PbO 9 N 3 polyhedra, and NSO 3 -Pb-NSO 3 frameworks. The dark brown color of the crystal is suggested to be caused by the absorption of blue wavelengths of light which is due to the excitation of excess electrons in potential wells produced by the NSO 3 -Pb-NSO 3 framework.

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Sulfamic acid and its N-substituted derivatives

Cited by 117 publications

References 107 publications

High Accuracy in Silico Sulfotransferase Models

High Accuracy in Silico Sulfotransferase Models

A molecular orbital study of the conformation (inversion and rotational barriers) and electronic properties of sulfamide

Crystal Growth and Structure of a New PbHNSO3 Crystal

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