N-Sulfonyl amines

Atkins, George M.; Burgess, Edward M.

doi:10.1021/ja00986a058

Cited by 72 publications

(22 citation statements)

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“…A HNSO 2 species is proposed to be the intermediate before the nucleophilic attack that gives the final products. The isolation of this species was reported a long time ago and showed a remarkable reactivity with nucleophiles . Kinetic experiments with 4‐nitrophenyl N ‐methylaminosulfonate in the presence of increasing concentrations of nucleophiles and buffers show no acceleratory effect, and the products formed from the reaction of HNSO 2 with different amine nucleophiles presented no detectable selectivity regarding the amine basicity.…”

Section: Resultsmentioning

confidence: 99%

“…The isolation of this species was reported a long time ago and showed a remarkable reactivity with nucleophiles. [55,56] Kinetic experiments with 4-nitrophenyl N-methylaminosulfonate in the presence of increasing concentrations of nucleophiles and buffers show no acceleratory effect, and the products formed from the reaction of HN¼SO 2 with different amine nucleophiles presented no detectable selectivity regarding the amine basicity. These observations suggest that the O-S bond cleavage was quite advanced in the reaction coordinate, with negligible nucleophilic participation.…”

Section: Correlation Between Structural Parameters and Effective Charmentioning

confidence: 99%

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Linear correlation between effective charge and bond length sensitivity to electronic effects in phosphoryl, sulfonyl, and sulfuryl compounds

Brandão

2013

J of Physical Organic Chem

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This work presents a linear correlation between bond length sensitivity (Δr/ΔpKlg) and effective charge by comparing a series of the following ROX compounds bearing phosphoryl (XP) and sulfonyl and sulfuryl (XS) moieties: phosphate monoester dianions and monoanions, phosphate diesters, phosphate and phosphorothioate triesters, 4‐Me, 3‐NO2 and 2‐ or 4‐NO2 substituted aryl benzene sulfonates, sulfate monoesters, and a previously determined series of sulfamate and mesylate esters. In every series for ROX compounds, the shortest C―O bond corresponds to the longest O―X bond, showing a linear correlation with the pKlg of the ROH parent compound. The chemical reasons for the extent of bond elongation are discussed, and a linear correlation is found between O―X bond length sensitivity and effective charge. These data show that bond length elongation depends on its strength regarding the equilibrium related to the full bond cleavage. Effective charges for phosphorothioate triesters and sulfonates are estimated, and the effective charge for aryl sulfamate esters is determined on the basis of the available linear free energy relationship data. It is expected that the observations of this paper will illuminate the effect of the electronic demand on the O―X bond lengths during phosphoryl, sulfonyl, and sulfuryl group transfer. Copyright © 2013 John Wiley & Sons, Ltd.

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Section: Resultsmentioning

confidence: 99%

Section: Correlation Between Structural Parameters and Effective Charmentioning

confidence: 99%

Linear correlation between effective charge and bond length sensitivity to electronic effects in phosphoryl, sulfonyl, and sulfuryl compounds

Brandão

2013

J of Physical Organic Chem

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“…One possible cause of yield diminution may be the known reaction of Et 3 N with sulfamoyl chloride yielding the zwitterionic HNS0 2 NEt 3 . 35 This reaction and the corresponding reaction of bases of similar strength may drain sulfamoyl chloride from the sulfamoylation reaction mixture. Irrespective of the mechanism, consistently rapid and high yielding reactions of 2',3'-protected nucleosides were observed with CaC0 3 or imidazole in DMF or NMP.…”

Section: -O-sulfamoyl-tubercidinmentioning

confidence: 99%

Herbicidally Active Sulfamoyl Nucleosides

Kristinsson

Nebel

O'Sullivan

et al. 1995

ACS Symposium Series

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“…N-Alkylsulfonylimines 1 (Figure 1) are unstable heterocumulenes that have been used as dipolarophiles with a variety of reactive dipoles. These compounds were first described by Atkins and Burgess in 1967, and their reaction with anilines and highly electron-rich alkenes was reported. [1] They are variously known throughout the literature as N-sulfonylamines, [1] N-sulfonylalkylamines, [2] N-alkylsulfonyl imides, [3] and N-alkylsulfonylimines, [4] and are not to be confused with N-sulfonylimines 3.…”

Section: Introductionmentioning

confidence: 99%