The Mechanisms of Diazonium Salt Reactions. II. A Redetermination of the Rates of the Thermal Decomposition of Six Diazonium Salts in Aqueous Solution1

1956 ◽  
Vol 78 (16) ◽  
pp. 3916-3920 ◽  
Author(s):  
DeLos F. DeTar ◽  
Alva Ray Ballentine
Keyword(s):  
Thermal Decomposition ◽  
Diazonium Salt ◽  
Diazonium Salts

Reactions of 2-(benzimidazol-2-yl)acetonitrile and its N-ethoxycarbonyl derivative with some azol-3-diazonium salts

1984 ◽  
Vol 49 (1) ◽  
pp. 275-279 ◽  
Author(s):  
Jan Slouka ◽  
Vojtěch Bekárek
Keyword(s):  
Diazonium Salt ◽  
Ethyl Chloroformate ◽  
Diazonium Salts

Coupling of 2-(1-ethoxycarbonyl-benzimidazol-2-yl)acetonitrile (II) with 5-methylpyrazol-3-diazonium (IIIa) or indazol-3-diazonium salt (IIIb) does not give the corresponding derivatives VIIa, VIIb of pyrazolo[3,2-c]-1,2,4-triazine but, instead, gives the corresponding 2-(3-azolyl)-1-oxo-1,2-dihydro-1,2,4-triazino-[4,5-a]benzimidazole-4-carbonitriles VIIIa, VIIIb. Coupling of 2-(benzimidazol-2-yl)acetonitrile (I) with the diazonium salt IIIa gives 7-amino-6-(benzimidazol-2-yl)-2-methylpyrazolo[3,2-c]-1,2,4-triazine (VIa) which, on reaction with ethyl chloroformate, undergoes cyclization to 2-methyl-12,13-dihydropyrazolo[3",2":3',4']-1,2,4-triazino[5',6':6,5]-pyrimido[3,4-a]benzimidazol-12-one (IXa). The compound VIa and 1-amino-2-(benzimidazol-2-yl)-1,2,4-triazono[4,3-b]indazole (VIb) are also formed by recyclization of the compounds VIIIa and VIIIb, respectively, in boiling aqueous pyridine.

scholarly journals AROMATIC SUBSTITUTION: PART IX. ON THE MECHANISM OF THE PSCHORR CYCLIZATION

1965 ◽  
Vol 43 (4) ◽  
pp. 940-949 ◽  
Author(s):  
R. A. Abramovitch ◽  
G. Tertzakian
Keyword(s):  
Acid Solution ◽  
Diazonium Salt ◽  
Equimolar Mixture ◽  
Diazonium Salts ◽  
Aromatic Substitution ◽  
Radical Process ◽  
Aqueous Acid Solution ◽  
Aqueous Acid ◽  
Catalyzed Reactions

The decomposition of the diazonium salt from 3-(o-aminobenzoyl)pyridine has been studied under various conditions. A competitive-type cyclization of an equimolar mixture of the diazonium salts of 2-aminobenzophenone and 2-amino-3′-nitrobenzophenone has also been carried out. The results are interpreted in terms of a radical process in the copper-catalyzed reactions. It is suggested that the uncatalyzed thermal decompositions in aqueous acid solution give rise to a diradical cation intermediate in equilibrium with the aryl cation.

1,4,8,11-Tetra[2-aryl-1-diazenyl]-1,4,8,11-tetraazacyclotetradecanes — Synthesis, characterization, and X-ray crystallography of the first tetrakistriazenes to be reported

2006 ◽  
Vol 84 (10) ◽  
pp. 1280-1289 ◽  
Author(s):  
Jeffery D Clarke ◽  
Keith Vaughan ◽  
Valerio Bertolasi
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Electrospray Mass Spectrometry ◽  
Diazonium Salt ◽  
Diazonium Salts ◽  
The Novel ◽  
Analogous Reaction ◽  
X Ray ◽  
X Ray Crystallography ◽  
The Mean

The reactions of a series of arene diazonium salts with 1,4,8,11-tetraazacyclotetradecane (cyclam) afford the novel compounds, the 1,4,8,11-tetra[2-aryl-1-diazenyl]-1,4,8,11-tetraazacyclotetradecanes (1a–1f), which are the first examples of tetrakistriazenes to be reported. The tetrakistriazenes were characterized by IR spectroscopy, proton and carbon NMR, elemental analysis, high resolution electrospray mass spectrometry, and X-ray crystallography. The analogous reaction of a diazonium salt with 1,4,7-triazacyclononane or 1,5,9-triazacyclododecane yields the tristriazenes 2, 3a, and 3b. The structures of compounds 1c and 1e were solved by X-ray crystallography at low temperature (150 K). Both molecules display a conformation where the four phenyltriazenyl groups point alternately upwards and downwards with respect to the mean macrocyclic plane.Key words: triazene, tetrakistriazene, cyclam, tetraazacyclotetradecane, X-ray, NMR, cyclic polyamines.

Triazene derivatives of (1,x)-diazacycloalkanes. Part VII. Synthesis of a series of 1-aryl-2-[3-(3-[2-aryl-1-diazenyl]-1,3-diazepan-1-ylmethyl)-1,3-diazepan-1-yl]-1-diazenes from the reaction of diazonium salts with mixtures of formaldehyde and 1,4-diaminobutane

2006 ◽  
Vol 84 (10) ◽  
pp. 1434-1441
Author(s):  
Reid Tingley ◽  
Keith Vaughan
Keyword(s):  
Diazonium Salt ◽  
Diazonium Salts ◽  
The Novel ◽  
Cage Structure ◽  
X Ray Crystallography ◽  
New Compounds ◽  
Type 3 ◽  
Bicyclic Molecules

A new series of bistriazenes, the 1-aryl-2-[3-(3-[2-aryl-1-diazenyl]-1,3-diazepan-1-ylmethyl)-1,3-diazepan-1-yl]-1-diazenes (8), has been synthesized from the reaction of diazonium salts with a mixture of 1,4-diaminobutane and formaldehyde. All new compounds of series 8 have been characterized by IR and NMR spectroscopy, and the elemental composition of selected examples has been verified by elemental analysis. The connectivity of the series has been unequivocally determined by X-ray crystallography. The new bistriazenes are important because the structure contains the novel saturated heterocycle, 1,3-diazepane. The general conclusion of this study is that alkanediamines with three or four carbon atoms in the spacer link between the nitrogen atoms give rise to the linear bicyclic molecules of type 2, in contrast to the case of ethylenediamine (two carbon atoms in spacer link), which affords molecules of type 3, which exemplify the cage structure of type 1.Key words: diazonium salt, triazene, bistriazene, diazepane, formaldehyde, nuclear magnetic resonance.

Open-chain nitrogen compounds. Part II. Preparation, characterization, and degradation of 1(3)-Aryl-3(1)-methyltriazenes; the effect of substituents on the reaction of diazonium salts with methylamine

1977 ◽  
Vol 55 (10) ◽  
pp. 1701-1709 ◽  
Author(s):  
T. Patrick Ahern ◽  
Handrick Fong ◽  
Keith Vaughan
Keyword(s):  
Degradation Products ◽  
Diazonium Salt ◽  
Diazonium Salts ◽  
Nitrogen Compounds ◽  
Open Chain ◽  
Effect Of Substituents ◽  
Electron Withdrawing Group

Treatment of the diazonium salts, X•C6H4N2+, with aqueous methylamine affords good yields of the monomethyltriazenes, X•C6H4•N=N•NHMe, when the substituent is a strongly electron-withdrawing group (X = o-, m-, and p-NO2; o-, m-, and p-CO2R; p-CN and p-COCH3). Preparation of the triazene from the p-bromobenzene diazonium salt was accompanied by formation of a pentaazadiene. Monomethyltriazenes were not obtained when diazonium salts containing other substituents (X = H, p-CH3, o-CF3, p-Cl, p-F, p-NMe2, p-OH, p-OCH3, p-Ph, p-NHCOCH3) were treated with methylamine. In these cases the products were either pentaazadiene, or 1,3-diaryltriazenes or unstable materials. The monomethyltriazenes vary considerably in stability and give rise to a number of different degradation products, which were either diaryltriazenes or 3-alkyl-1,3-diaryltriazenes or simply arylamines. 1(3)-(p-Nitrophenyl)-3(1)-methyltriazene was found to be a moderately effective methylating agent.

Diazonium salt-based photoiniferter as a new efficient pathway to clay–polymer nanocomposites

RSC Advances ◽  
2016 ◽  
Vol 6 (91) ◽  
pp. 88126-88134 ◽  
Author(s):  
Hanène Salmi-Mani ◽  
Zouhair Ait-Touchente ◽  
Aazdine Lamouri ◽  
Benjamin Carbonnier ◽  
Jean-François Caron ◽  
...  
Keyword(s):  
Free Radical ◽  
Polymer Nanocomposites ◽  
Glycidyl Methacrylate ◽  
Diazonium Salt ◽  
Diazonium Salts ◽  
Mass Loading ◽  
Organic Mass ◽  
Free Radical Photopolymerization

Diazonium salts were used to prepare clay–polymer nanocomposites by living free radical photopolymerization of glycidyl methacrylate. The resulting intercalated nanocomposites have an organic mass loading of ∼41 wt% and a polymer-rich surface.

scholarly journals Flexible Chemiresistive Nitrogen Oxides Sensors Based on a Nanocomposite of Polypyrrole- Reduced Graphene Oxide Grafted Carboxybenzene Diazonium Salts.

2021 ◽  
Author(s):  
Djamil GUETTICHE ◽  
Ahmed MEKKI ◽  
BENMOULOUD Lilia ◽  
Tighilt Fatma-zohra ◽  
Amar BOUDJELLAL
Keyword(s):  
Graphene Oxide ◽  
Reduced Graphene Oxide ◽  
Spin Coating ◽  
Diazonium Salt ◽  
Covalent Bonding ◽  
Diazonium Salts ◽  
Reduced Graphene ◽  
One Step ◽  
Higher Sensitivity

Abstract Nanocomposites of polypyrrole/reduced graphene oxide (PPy/rGO) and polypyrrole/ functionalized reduced graphene oxide with aryl 4-carboxybenzene diazonium salt (PPy/rGO-aryl-COOH) were prepared through covalent bonding by simple one-step chemical oxidative synthesis. The as-prepared nanocomposites were deposited on BOPET substrate by spin coating to test their chemiresistive sensitivity properties on a homemade modular for online detection of (NO2) vapors at ambient temperature. Results showed that PPy/rGO-aryl-COOH forms a homogeneous nanocomposite within the size of 80 nanometers and improvement of the crystalline ordering. The more enhanced NO2 sensing properties have been shown by PPy/rGO- aryl-COOH in terms of higher sensitivity (1.01%/ppm), the faster response time (129 s), and the detection limit of (2ppm). Reproducibility features were also investigated.Moreover, humidity rates and temperature effects were also tested. Finally, impedance spectroscopy is conducted in the fresh air and in the presence of gas. These results highlight the paramount role of functionalization of reduced graphene oxide (rGO-aryl-COOH).

scholarly journals SPECIFIC INHIBITION OF ACID PHOSPHATASE-3 IN POLLEN OF MAIZE BY THE DIAZONIUM SALT FAST GARNET GBC

1969 ◽  
Vol 17 (11) ◽  
pp. 734-737 ◽  
Author(s):  
YOEL EFRON
Keyword(s):  
Acid Phosphatase ◽  
Phosphatase Activity ◽  
Acid Phosphatase Activity ◽  
Diazonium Salt ◽  
Specific Inhibitor ◽  
Inorganic Ions ◽  
Diazonium Salts ◽  
Specific Inhibition ◽  
Maize Pollen ◽  
Fast Blue

Fast garnet GBC, a diazonium salt commonly used for localization of acid phosphatase activity, was found to be a specific inhibitor for AP3, one of three acid phosphatase enzymes present in maize pollen. This enzyme was not inhibited by fast blue RR or fast blue BB, two other diazonium salts. A possible Inhibition by accompanying inorganic ions was ruled out.

Synthesis and characterization of a series of 4-methyl-1-[2-aryl-1-diazenyl]-1,4-diazepanes and 1,4-di-[2-aryl-1-diazenyl]-1,4-diazepanes

2004 ◽  
Vol 82 (12) ◽  
pp. 1725-1735 ◽  
Author(s):  
Shasta Lee Moser ◽  
Keith Vaughan
Keyword(s):  
Nmr Assignments ◽  
Diazonium Salt ◽  
Variable Temperature ◽  
2D Nmr ◽  
Diazonium Salts ◽  
X Ray Diffraction ◽  
X Ray ◽  
New Compounds ◽  
C Nmr

1-Methylhomopiperazine was coupled with a series of diazonium salts to afford the 4-methyl-1-[2-aryl-1-diazenyl]-1,4-diazepanes (6), a new series of triazenes. These compounds are, in the main, stable crystalline solids (some of the series are stable oils), and they have been characterized by 1H and 13C NMR spectroscopy, IR spectroscopy, and mass spectrometry. NMR assignments were determined by 2D NMR and variable-temperature NMR experiments and by comparison with model compounds. A second series of new compounds, namely, 1,4-di-[2-aryl-1-diazenyl]-1,4-diazepanes (5), were prepared by coupling unsubstituted homopiperazine (1,4-diazepane) with 2 molar equivalents of the diazonium salt and were similarly characterized. The crystal and molecular structure of the parent member of this bis-triazene series (5, X = H) has been determined by single-crystal X-ray diffraction analysis.Key words: triazene, bis-triazene, diazenyl, bis-diazenyl, diazonium salt, NMR, diazepane.

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