Reduction of Nitroguanidine. II. Preparation and Properties of Nitrosoguanidine<sup>1</sup>

Sabetta, V. J.; Himmelfarb, David; Smith, Gordon B.

doi:10.1021/ja01315a047

Cited by 9 publications

(5 citation statements)

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“…Synthesis of Nitrosoguanidine, Methylnitrosoguanidine, and Their Complexes. Although nitrosoguanidine 1a is readily prepared by aqueous zinc reduction at increased temperatures, 21,43,44 the yield is markedly dependent upon conditions. The original figure of 38% 21 is seldom matched by more recent reports that typically return values of <8%.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

2,3,5-Metallotriazoles: Amphoteric Mesoionic Chelates from Nitrosoguanidines

et al. 2021

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Soluble nitrosoguanidine- and N-methylnitrosoguanidine-based metallotriazole complexes of ruthenium(II) monocarbonyls have been prepared and characterized. Both nitrosoguanidines prove to be strong chelates with the formally π-accepting nitroso nitrogen binding cis to carbon monoxide and a π-donating amide trans to the CO. The resulting ensemble consists of ruthenium examples of 1-metallo-2,3,5-triazoles. The ruthenium coordination sphere is completed by anions, either H–, Cl–, or Ph–, trans to the nitroso group as well as two mutually trans PPh3 groups. The π-donating amide group is formally sp2 hybridized with a planar nitrogen to give a strongly bound five-membered chelating anion. Together, these results illustrate the remarkable potential for the nitrosoguanidinates as a family of new metal chelates.

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Section: ■ Results and Discussionmentioning

confidence: 99%

2,3,5-Metallotriazoles: Amphoteric Mesoionic Chelates from Nitrosoguanidines

et al. 2021

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“…Elemental analysis was performed by the Galbraith Laboratory of Knoxville, Tenn. Nitroguanidine was synthesized according to Davis et al (1925). Nitrosoguanidine was prepared by reduction of nitroguanidine according to Sabetta et al (1935). Ammeline, ammelide, and thioammeline were products of the American Cyanamid Corp. Cyanuric acid was obtained from Fluka AG.…”

Section: Methodsmentioning

confidence: 99%

A New Class of Xanthine Oxidase Inhibitors Isolated from Guanidinium Salts^*

Fridovich¹

1965

Biochemistry

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“…In general, one major absorption peak was exhibited in the ultraviolet region by the compounds investigated and this peak most strongly illustrated the change in absorbance with • change in pH of the medium. By employing a large number of buffered solutions over the pH range (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14), it was possible to plot a smooth curve showing the relationship between pH and absorption. By careful measurement then the pK value could be easily obtained graphically.…”

Section: Methodsmentioning

confidence: 99%

The Thermodynamics of Ionization of Amino Acids. I. The Ionization Constants of γ-Aminobutyric Acid

King¹

1954

J. Am. Chem. Soc.

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The electromotive forces of cells with hydrogen and silver-silver chloride electrodes which contained buffer mixtures either of -aminobutyric acid and hydrochloric acid or of the amino acid, its sodium salt, and sodium chloride were measured at 5°i ntervals from 10 to 50°. From these data the thermodynamic ionization constants, K¡ for the ionization of the carboxyl group and K2 for the ionization of the ammonium group, were calculated. The changes in free energy, enthalpy, entropy and heat capacity associated with the ionization in the standard state can be obtained from the equations -log K¡ = (1209.

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Reduction of Nitroguanidine. II. Preparation and Properties of Nitrosoguanidine¹

Cited by 9 publications

References 0 publications

2,3,5-Metallotriazoles: Amphoteric Mesoionic Chelates from Nitrosoguanidines

2,3,5-Metallotriazoles: Amphoteric Mesoionic Chelates from Nitrosoguanidines

A New Class of Xanthine Oxidase Inhibitors Isolated from Guanidinium Salts^*

The Thermodynamics of Ionization of Amino Acids. I. The Ionization Constants of γ-Aminobutyric Acid

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Reduction of Nitroguanidine. II. Preparation and Properties of Nitrosoguanidine1

Cited by 9 publications

References 0 publications

2,3,5-Metallotriazoles: Amphoteric Mesoionic Chelates from Nitrosoguanidines

2,3,5-Metallotriazoles: Amphoteric Mesoionic Chelates from Nitrosoguanidines

A New Class of Xanthine Oxidase Inhibitors Isolated from Guanidinium Salts*

The Thermodynamics of Ionization of Amino Acids. I. The Ionization Constants of γ-Aminobutyric Acid

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Reduction of Nitroguanidine. II. Preparation and Properties of Nitrosoguanidine¹

A New Class of Xanthine Oxidase Inhibitors Isolated from Guanidinium Salts^*