Trinitromethanide and tricyanomethanide salts restricted to C, H, N, and O atoms

Gunasekaran, Ananthakrishnan; Boyer, J. H.

doi:10.1002/hc.520030525

Cited by 3 publications

(3 citation statements)

References 18 publications

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“…136 In contrast, the reaction of the t-BuC 60anion ( 153 When strong carbon acids such as nitroform (HC-(NO 2 ) 3 ) and cyanoform (HC(CN) 3 ) were allowed to react with diphenylcyclopropenone oxime, carbocation-carbanion salts 1-(hydroxyamino)-2,3-diphenylcyclopropenylium trinitromethide (155a) and tricyanomethide (155b) were obtained as yellow solids in 85% and 65% yield, respectively (eq 88). 139 Tris(dimethylamino)cyclopropenylium cation (70) formed salts with the tetracyanoquinodimethane (TCNQ) radical anion. These salts afforded two different crystals, depending on the polarity of the solvent.…”

Section: Carbocation−carbanion Salt Formationmentioning

confidence: 99%

“…When strong carbon acids such as nitroform (HC(NO 2 ) 3 ) and cyanoform (HC(CN) 3 ) were allowed to react with diphenylcyclopropenone oxime, carbocation−carbanion salts 1-(hydroxyamino)-2,3-diphenylcyclopropenylium trinitromethide ( 155a ) and tricyanomethide ( 155b ) were obtained as yellow solids in 85% and 65% yield, respectively (eq 88) …”

Section: Carbocation−carbanion Salt Formationmentioning

confidence: 99%

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Cyclopropenylium Cations, Cyclopropenones, and HeteroanaloguesRecent Advances

2003

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Section: Carbocation−carbanion Salt Formationmentioning

confidence: 99%

Section: Carbocation−carbanion Salt Formationmentioning

confidence: 99%

Cyclopropenylium Cations, Cyclopropenones, and HeteroanaloguesRecent Advances

2003

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“…Indeed, a unimolecular versus a bimolecular route is often determined by the stability of the potential carbocation intermediate. Interest in carbocations also comes from the synthesis and characterization of ionic or highly polar C + C − compounds 2–6, such as (H 2 N) 3 C + C(NO 2 ) 3 − 5.…”

Section: Introductionmentioning

confidence: 99%

Electrostatic potential as a measure of gas phase carbocation stability

Robbins

Jin

Brinck

et al. 2006

Int J of Quantum Chemistry

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Assessment of the relative stabilities of carbocations is important for interpreting reaction mechanisms as well as in organic synthesis. A common approach is in terms of hydride affinities; however these depend on a second system, a neutral molecule, as well as the ion. In the present work, we propose a measure of gas phase carbocation stability that is dependent solely on the properties of the ion: the magnitude of the most positive surface electrostatic potential associated with the carbon framework. This quantity, labeled V S,max , reflects a key factor, the extent to which the positive charge has been delocalized. We have computed V S,max for 28 carbocations, and we show that the overall trends predicted are physically meaningful in terms of experimental observations. Mulliken atomic charges are not satisfactory for this purpose.

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Potassium‐, Ammonium‐, Hydrazinium‐, Guanidinium‐, Aminoguanidinium‐, Diaminoguanidinium‐, Triaminoguanidinium‐ and Melaminiumnitroformate – Synthesis, Characterization and Energetic Properties

Göbel

Klapötke

2007

Zeitschrift anorg allge chemie

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Energetic salts containing the nitroformate (trinitromethanide) anion with several nitrogen‐rich cations were investigated, including ammonium nitroformate (ANF), melaminium nitroformate (MNF), guanidinium nitroformate monohydrate (GNFH), aminoguanidinium nitroformate (AGNF), diaminoguanidinium nitroformate (DAGNF) as well as triaminoguanidinium nitroformate (TAGNF). All salts were characterized using vibrational spectroscopy (IR, Raman), mass spectrometry, multinuclear NMR spectroscopy and elemental analysis. The thermal decomposition of the salts was monitored using differential scanning calorimetry. In addition, the impact, friction and electrostatic sensitivity data were determined. Theoretical calculations were carried out in order to predict performance data such as detonation velocities and detonation pressures. The crystal structures of ANF, MNF, GNFH, AGNF, DAGNF and TAGNF were determined using single crystal X‐ray diffraction. In addition, a second polymorph of MNF was determined crystallographically as well as the crystal structures of MNF with methanol and MNF with dimethylsulfoxide. Finally, new polymorphs of potassium nitroformate (KNF) and hydrazinium nitroformate (HNF) were characterized using single crystal X‐ray diffraction.

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Trinitromethanide and tricyanomethanide salts restricted to C, H, N, and O atoms

Cited by 3 publications

References 18 publications

Cyclopropenylium Cations, Cyclopropenones, and HeteroanaloguesRecent Advances

Cyclopropenylium Cations, Cyclopropenones, and HeteroanaloguesRecent Advances

Electrostatic potential as a measure of gas phase carbocation stability

Potassium‐, Ammonium‐, Hydrazinium‐, Guanidinium‐, Aminoguanidinium‐, Diaminoguanidinium‐, Triaminoguanidinium‐ and Melaminiumnitroformate – Synthesis, Characterization and Energetic Properties

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