Sulphamic Acid and Derivatives

Benson, G. Anthony; Spillane, William J.

doi:10.1002/0470034394.ch22

Cited by 9 publications

(4 citation statements)

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“…In 1980 sulfamic acid and its N-substituted derivatives were reviewed in Chemical Reviews , effectively updating an earlier 1940 review also in Chemical Reviews . In 1991 the subject was again comprehensively reviewed, and since a further 20 years have passed it was felt that there was a need for a new review that could bring together the many and diverse areas of sulfamic acid chemistry and especially the whole area of sulfamate esters, RNHSO 2 OR, which has emerged in the last 18 or so years as being of immense importance in biological and medicinal chemistry. This task rather unexpectedly received new immediacy and urgency when it was reported recently that the 1980 Chemical Reviews article for a time topped the ACS list as “the most read” Chemical Reviews in 2011 on a list containing in the main articles that had appeared over the past few years.…”

Section: Introductionmentioning

confidence: 99%

Sulfamic Acid and Its N- and O-Substituted Derivatives

2013

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Section: Introductionmentioning

confidence: 99%

Sulfamic Acid and Its N- and O-Substituted Derivatives

2013

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“…Sulfamate esters, RNHSO 2 OR I , have been prepared and tested for a wide range of properties including uses as herbicides, pharmaceutical agents, and artificial sweeteners . In the 1990s, interest has heightened because of further discoveries with regard to the efficacy of these esters, for example, in the inhibition of carbonic anhydrase (an enzyme linked to abnormally high intraocular pressure causing glaucoma and leading to blindness), in the use of the clinically important sulfamate anticonvulsant topiramate, in the inhibition of ACAT (lowering of cholesterol levels), and most importantly in the use of certain steroidal sulfamates to inhibit estrone sulfatase (the enzyme associated with the development of breast cancer).…”

Section: Introductionmentioning

confidence: 99%

Change in Rate-Determining Step in an E1cB Mechanism during Aminolysis of Sulfamate Esters in Acetonitrile

et al. 2001

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The kinetics of the reactions of the nitrogen-sulfur(VI) esters 4-nitrophenyl N-methylsulfamate (NPMS) with a series of pyridines and a series of alicyclic amines and of 4-nitrophenyl N-benzylsulfamate (NPBS) with pyridines, alicyclic amines, and a series of quinuclidines have been investigated in acetonitrile (ACN) in the presence of excess amine at various temperatures. Pseudo-first-order rate constants (k(obsd)) have been obtained by monitoring the release of 4-nitrophenol/4-nitrophenoxide. From the slope of a plot of k(obsd) vs [amine], second-order rate constants (k'(2)) have been obtained for the pyridinolysis of NPMS, and a Brønsted plot of log k'(2) vs pK(a) of pyridine gave a straight line with beta = 0.45. However, aminolysis with alicyclic amines of NPMS gave a biphasic Brønsted plot (beta(1) = 0.6, beta(2) approximately equal to 0). Pyridinolysis and aminolysis with alicyclic amines and quinuclidines of NPBS also gave similar biphasic Brønsted plots. This biphasic behavior has been explained in terms of a mechanistic change within the E1cB mechanism from an (E1cB)(irrev) (less basic amines) to an (E1cB)(rev) (more basic amines), and the change occurs at approximately the pK(a)'s (in ACN) of NPMS (17.94) and NPBS (17.68). The straight line Brønsted plot for NPMS with pyridines occurs because the later bases are not strong enough to substantially remove the substrate proton and initiate the mechanistic change observed in the reaction of NPMS with the strong alicyclic amines and quinuclidines. An entropy study supports the change from a bimolecular to a unimolecular mechanism. This is the first clear demonstration of this E1cB mechanistic changeover involving a nitrogen acid substrate.

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“…1) is used in organic syntheses to yield, for example, 1H,3H-2,1,3-benzothiadiazin-4-one-2,2-dioxide (BTDD, Fig. 1) [4], a speci¢c reaction which is representative for a broad range of syntheses [5]. Sulfamate (H P N^SO Q 3 ) is used mainly as a precursor for the arti¢cial sweetener, cyclamate (cf.…”

Section: Introductionmentioning

confidence: 99%

“…Sulfamate (H P N^SO Q 3 ) is used mainly as a precursor for the arti¢cial sweetener, cyclamate (cf. [5]) as well as in industrial and household descaling [6]. Sulfamate can thus be expected in many sewage works.…”

Section: Introductionmentioning

confidence: 99%

Bacterial cleavage of nitrogen to sulfone bonds in sulfamide and 1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide: formation of 2-nitrobenzamide byGordoniasp.

Rein

Cook

1999

FEMS Microbiology Letters

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Pure cultures of aerobic bacteria were isolated which could utilize sulfamate, sulfamide or 1H‐2,1,3‐benzothiadiazin‐4(3H)‐one 2,2‐dioxide (BTDD) as sole source of sulfur for growth and thus cleave a N–S(O)x bond. The molar growth yields indicated that each source of sulfur was utilized quantitatively. This was confirmed directly for Gordonia sp. strain BT2 utilizing BTDD, which was converted quantitatively via an unidentified intermediate to 2‐nitrobenzamide. Another isolate, strain BT1, could utilize saccharin to yield salicylamide, thus cleaving both the N–S(O)x and C–S(O)x bonds.

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Sulphamic Acid and Derivatives

Cited by 9 publications

References 0 publications

Sulfamic Acid and Its N- and O-Substituted Derivatives

Sulfamic Acid and Its N- and O-Substituted Derivatives

Change in Rate-Determining Step in an E1cB Mechanism during Aminolysis of Sulfamate Esters in Acetonitrile

Bacterial cleavage of nitrogen to sulfone bonds in sulfamide and 1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide: formation of 2-nitrobenzamide byGordoniasp.

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