Hydrazonium Salts Research Articles

Preparation, Characterization, Thermal Degradation, and Crystal Structures of Hydrazinium and Ammonium Salts of Ethylenediaminetetraacetic Acid and Seven Coordinated N2H5[Cd(Hedta)(H2O)].H2O

Dihydrazinium, hydrazinium, hydrazinium ammonium, and ammonium salts of ethylenediaminetetraacetic acid (H4edta) such as (N2H5)2H2edta, N2H6H2edta, N2H5NH4H2edta and (NH4)2H2edta have been prepared and characterized by elemental analyses, hydrazine analysis, conductivity measurements, and infrared spectra. The thermal degradation studies reveal that these compounds undergo complete and multi step decomposition with or without melting. The IR spectra show that in all the cases the acidic protons are attached to the tertiary nitrogen atoms of edta and all the salts exist as zwitterions. The X-ray single-crystal data and the corresponding ORTEP diagram of the dihydrazinium and hydrazonium salts clearly support and confirm the data. Hydrazinium hydrogenethylenediaminetetraacetato aquo cadmium(II) monohydrate, N2H5[Cd(Hedta)(H2O)].H2O, has been synthesized and structurally characterized. The crystal belongs to orthorhombic crystal system and the space group Pbca. The crystal data are the following: a = 9.423 Å, b = 4.406 Å, c = 23.838 Å, α = β = γ = 90°, V = 3236 Å3, Z = 8, Dc = 1.932 Mg/m3, μ = 1.412 mm−1, F(000) = 1904, the final R = 0.0190, and wR = 0.0562 for 3707 observed reflection with I›2σ(I).

ChemInform Abstract: An Elimination Reaction of N-Carbomethoxy-N,N-dimethylhydrazonium Salts to Alkyl Nitriles.

Abstract A new kind of elimination of hydrazonium salts to alkyl nitriles has been developed. The reaction of hydrazones and chloroformates results in the formation of hydrazonium salts, which react in situ with water to afford alkyl nitriles. The elimination is adapted to a range of solvents and gives good yields of α-secondary and tertiary alkyl-substituted nitriles.

First tandem nucleophilic addition–electrophilic amination reaction of Eschenmoser’s salts: synthesis of cyclic and spiro-fused hydrazonium salts

A series of cyclic and spiro-fused hydrazonium salts was prepared by tandem nucleophilic addition–electrophilic amination reactions. The method presented makes use of Eschenmoser’s salt or benzotriazole aminals and 2-hydroxylamino-4,5-dihydroimidazolium- O-sulfonate. The products structures were determined by X-ray analysis.

Synthesis of N,N’-Linked Isothiazolium Salts via Intramolecular Cyclocondensation of Hydrazonium Salts

Interaction of β -thiocyanatovinyl aldehydes with N-amino heterocycles leads to formation of α, β - unsaturated hydrazonium salts dependent on the functional surroundings. The latter can undergo further intramolecular cyclocondensation giving rise to N,N′-linked isothiazolium salts as the final product. The isolated hydrazonium salts, not undergoing ring formation, have s-trans conformation of the azadiene system

Palladium(0)-catalyzed Amino-Heck Reaction of γ,δ-Unsaturated Ketone N,N,N-Trimethylhydrazonium Salts

Oxidative addition of N,N,N-trialkylhydrazonium salts takes place to a palladium(0) complex, resulting the formation of alkylideneaminopalladium(II) species. This N-N bond scission process is applied to the transformationof γ,δ-unsaturated ketone hydrazonium salts to pyrroles by amino-Heck reaction.

Structure of N, N-dimethylhydrazone alkylation products

Alkylation of 1,1-dimethylhydrazone-4- and -3-pyridinaldehydes has been shown, by means of multinucleus 1D- and 2D NMR spectroscopy and quantum chemistry (ab initio), to proceed exclusively by the pyridine nitrogen atom to form the corresponding pyridinium halides. At the same time, 1,1-dimethylhydrazone benzaldehyde is alkylated to the amine nitrogen with the formation of hydrazonium salts.

An elimination reaction of N-carbomethoxy-N,N-dimethylhydrazonium salts to alkyl nitriles

A new kind of elimination of hydrazonium salts to alkyl nitriles has been developed. The reaction of hydrazones and chloroformates results in the formation of hydrazonium salts, which react in situ with water to afford alkyl nitriles. The elimination is adapted to a range of solvents and gives good yields of α-secondary and tertiary alkyl-substituted nitriles.

Asymmetric Synthesis of 1-Substituted Tetrahydroisoquinolines by Nucleophilic Addition to Hydrazonium Ions. Application to the Enantioselective Syntheses of (+)- and (−)-Salsolidines and (−)-Cryptostyline II

Nucleophilic addition of carbon nucleophiles and metal hydride reagents to hydrazonium salts modified by optically active 2-substituted pyrrolidine auxiliaries leads to highly enantioselective synthesis of 1-substituted tetrahydroisoquinolines. This methodology was applied to asymmetric synthesis of the title isoquinoline alkaloids.

Asymmetric synthesis of 1-substituted tetrahydroisoquinolines by nucleophilic addition to hydrazonium ions. Application to the enantioselective syntheses of (+)- and (−)-salsolidines and (−)-cryptostyline II

Nucleophilic addition of carbon nucleophiles and metal hydride reagents to hydrazonium salts modified by optically active 2-substituted pyrrolidine auxiliaries leads to highly enantioselective synthesis of 1-substituted tetrahydroisoquinolines. This methodology was applied to asymmetric synthesis of the title isoquinoline alkaloids.

ChemInform Abstract: closo‐Borate Anions B10H2‐ 10 and B12H2‐ 12 in Hydrazino‐Complexes of Ni(II) and Pb(II) and in Hydrazonium Salts

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Elimination reactions of hydrazonium salts: experimental and theoretical evidence for a large stereoelectronic effect of nitrogen

Elimination of trimethylamine from hydrazonium salts is promoted by base (methoxide ion in methanol). The mechanism is characterized as E2 as shown by substituent effects (ρ=+2.57), Bronsted coefficients, a primary kinetic isotope effect (k H /k D =2.10), and solvent effects. Variation in the leaving group shows that N-N bond cleavage is less well advanced in the transition state than C-H bond breaking

ChemInform Abstract: Action of Alkylmagnesium and Alkyllithium Reagents on Some Quaternary Hydrazonium Salts.

AbstractThe diaryl ketone hydrazones (I) are converted to the quaternary hydrazonium salts (III) and (VII).

Action of alkylmagnesium and alkyllithium reagents on some quaternary hydrazonium salts

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAction of alkylmagnesium and alkyllithium reagents on some quaternary hydrazonium saltsPeter A. S. Smith and Calvin R. MessingCite this: J. Org. Chem. 1988, 53, 13, 2959–2965Publication Date (Print):June 1, 1988Publication History Published online1 May 2002Published inissue 1 June 1988https://doi.org/10.1021/jo00248a011RIGHTS & PERMISSIONSArticle Views217Altmetric-Citations6LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (947 KB) Get e-Alerts Get e-Alerts

Hydrazonium(2+) hexafluorosilicate, N2H6SiF6: a NaCl-type structure with two-dimensional hydrogen-bonding networks

Hydrazonium(2+) hexafluorosilicate, N2H6SiF6, at room temperature has an orthorhombic (Pbca, Z = 4), pseudotetragonal unit cell (a = 7.605(1) Å, b = 7.586(2) Å, c = 8.543(1) Å). The structure consists of centrosymmetric N2H62+ and SiF62− ions arranged in a NaCl-type packing and connected by hydrogen bonds to two-dimensional N2H6–SiF6 layers parallel to (001). All H atoms are engaged in hydrogen bonding. Four of the six [Formula: see text] bonds to each cation are normal but significantly bent; the other two are trifurcated, [Formula: see text], but the out-of-layer component of the trifurcated bond is relatively unimportant. The N2H6SiF6 structure is compared in some detail with the structures of other hydrazonium(2+) salts, with particular attention to the N—N bond length, to the "effective" size of the N2H62+ ion, and to the tendency of this ion to form bent hydrogen bonds.

Thermal cleavage of selected aldehyde hydrazonium salts

Thermal cleavage of selected aldehyde hydrazonium salts

Synthesis of hydrazonium salts

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of hydrazonium saltsPatrick J. Foley Jr., Elizabeth Anderson, and Fred DeweyCite this: J. Chem. Eng. Data 1969, 14, 2, 272–274Publication Date (Print):April 1, 1969Publication History Published online1 May 2002Published inissue 1 April 1969https://doi.org/10.1021/je60041a043RIGHTS & PERMISSIONSArticle Views103Altmetric-Citations-LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (314 KB) Get e-Alerts Get e-Alerts

Studies on Hydrazine: Heats of Solution of Hydrazonium Salts at 25°. II

Studies on Hydrazine: Heats of Solution of Hydrazonium Salts at 25°. II

Studies on Hydrazine: Heats of Solution of Hydrazonium Salts at 25°

Studies on Hydrazine: Heats of Solution of Hydrazonium Salts at 25°

Studies on Hydrazine: Heat Capacities of Aqueous Hydrazonium Salts at 20 and 25°1

Studies on Hydrazine: Heat Capacities of Aqueous Hydrazonium Salts at 20 and 25°¹

Studies on Hydrazine: Transition Points and Dissociation Pressures of Hydrated Hydrazonium Salts

Studies on Hydrazine: Transition Points and Dissociation Pressures of Hydrated Hydrazonium Salts