The Meyer Reaction of Phenylnitromethane in Acid. I. The Reactions of Phenyl-aci-nitromethane in Acid

1971 ◽  
Vol 49 (21) ◽  
pp. 3483-3488 ◽  
Author(s):  
J. T. Edward ◽  
P. H. Tremaine
Keyword(s):  
Sulfuric Acid ◽  
Room Temperature ◽  
Isotope Effects ◽  
Substituent Effects ◽  
Benzohydroxamic Acid ◽  
Aqueous Sulfuric Acid

Phenyl-aci-nitromethane reacts in aqueous sulfuric acid at room temperature to form phenylnitromethane and benzohydroxamic acid. The relative amounts of these two products depend on the concentration of the acid. Benzohydroxamic acid is formed by reaction of the intermediate, benzonitrile oxide, with water.Solvent effects, substituent effects, and isotope effects have been studied to determine mechanisms for these reactions of phenyl-aci-nitromethane.

Substituent Effects of Phosphorus and Arsenic Containing Groups in Aromatic Substitution. IV. Nitration of Aromatic Phosphine Oxides

1975 ◽  
Vol 53 (10) ◽  
pp. 1468-1474 ◽  
Author(s):  
Edmund Malinski ◽  
Antonina Piekos ◽  
Tomasz A. Modro
Keyword(s):  
Sulfuric Acid ◽  
Benzene Ring ◽  
Phosphorus Atom ◽  
Substituent Effects ◽  
Ortho Position ◽  
Phosphine Oxides ◽  
Aromatic Substitution ◽  
Tertiary Phosphine ◽  
Aqueous Sulfuric Acid

The nitration of some tertiary phosphine oxides ArP(O)R2 in aqueous sulfuric acid has been investigated. All compounds studied react as conjugate acids. When the phosphinyl group is bonded directly to the benzene ring, high deactivation and meta-orientation is found, accompanied in most cases by some substitution at the ortho position. The substituent effects of the "quasiphosphonium" group P(OH)R2+are compared with those of structurally related systems and are discussed in terms of pπ–dπ, interactions of the oxygen and the phosphorus atom.

The Meyer Reaction of Phenylnitromethane in Acid. II. Reactions in Acid of Benzonitrile Oxide and Benzohydroxamic Acid

1971 ◽  
Vol 49 (21) ◽  
pp. 3489-3492 ◽  
Author(s):  
J. T. Edward ◽  
P. H. Tremaine
Keyword(s):  
Sulfuric Acid ◽  
Room Temperature ◽  
Detailed Mechanism ◽  
Benzohydroxamic Acid ◽  
Dilute Sulfuric Acid ◽  
Rate Profile ◽  
Kinetics Of ◽  
Hydrolysis Of

The kinetics of the transformation of benzonitrile oxide in dilute sulfuric acid into benzohydroxamic acid have been followed by u.v. spectrophotometry at a temperature near room temperature. A mechanism is proposed on the basis of the effects of substituents and sulfuric acid concentration.The rate profile for the hydrolysis of benzohydroxamic acid in hot dilute sulfuric acid has been obtained.The results of these studies are applied to the detailed mechanism of the Meyer rearrangement – hydrolysis of phenylnitromethane in acid.

Mechanisms of bromination of uracil derivatives. 4. Formation of adducts in acidic aqueous solutions and their dehydration to 5-bromouracils

1979 ◽  
Vol 57 (6) ◽  
pp. 626-634 ◽  
Author(s):  
Oswald S. Tee ◽  
Sujit Banerjee
Keyword(s):  
Sulfuric Acid ◽  
Aqueous Solutions ◽  
Isotope Effects ◽  
Uracil Derivatives ◽  
Aqueous Sulfuric Acid ◽  
Acid Catalyzed

The reactions of bromine with uracil, 1-methyluracil, 3-methyluracil, and with 1,3-dimethyluracil in 0.125–2.0 M aqueous sulfuric acid have been examined. Under these conditions rapid attack by bromine upon the uracil leads to the formation of an observable intermediate, a 5-bromo-5,6-dihydro-6-hydroxyuracil, which subsequently undergoes slow acid-catalyzed dehydration to the appropriate 5-bromouracil. The intermediates derived from uracil and 3-methyluracil also show acid independent dehydration. The dehydration of the adduct derived from 6-methyluracil proceeds much more rapidly and so precludes observation of that adduct. The dehydrations show significant primary isotope effects for the rupture of C(5)—H bonds of the intermediates. The mechanistic implications of these results are discussed.

Solvent isotope effects on pKa of anilinium ions in aqueous sulfuric acid

1973 ◽  
Vol 77 (12) ◽  
pp. 1557-1562 ◽  
Author(s):  
J. L. Jensen ◽  
M. P. Gardner
Keyword(s):  
Sulfuric Acid ◽  
Isotope Effects ◽  
Aqueous Sulfuric Acid ◽  
Solvent Isotope ◽  
Solvent Isotope Effects

Electrochemistry of Gold in Aqueous Sulfuric Acid Solutions under Neural Stimulation Conditions

2005 ◽  
Vol 152 (7) ◽  
pp. E212 ◽  
Author(s):  
Daniel R. Merrill ◽  
Ionel C. Stefan ◽  
Daniel A. Scherson ◽  
J. Thomas Mortimer
Keyword(s):  
Sulfuric Acid ◽  
Neural Stimulation ◽  
Acid Solutions ◽  
Aqueous Sulfuric Acid ◽  
Sulfuric Acid Solutions
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