Ethane 1,2-Diamineborane

Kelly, Henry C.; Edwards, John O.

doi:10.1021/ja01503a023

Cited by 39 publications

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“…We were unable to separate and purify the components of these mixtures. The products were water-and air-sensitive oils similar to those described by Kelly and Edwards (6). The reaction involving (CH3)3NBF3 gave a white solid which turned to an oil on exposure to air (7).…”

Section: Methodssupporting

confidence: 65%

Preparation of the Piperazine– and Triethylenediamine–Monoborane Adducts of BH₃, BH₂F, BHF₂, and BF₃

Vanpaasschen¹,

Geanangel²

1975

Can. J. Chem.

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J. M. VANPAASSCHEN and R. A. GEANANGEL. Can. J. Chem. 53.723 (1975). The new compounds, triethylenediamine-BH2F, -BHF2, -BFJ and piperazine-BH2F, -BHF2, -BFJ have been isolated and characterized from the base displacement reactions involving the diamine and the trimethylamine-fluoroboranes. By this method only the monoborane adducts of the difunctional amines are formed. The stability of these monoborane adducts is rationalized from a mechanistic point of view. The proton and boron-1 1 n.m.1. and i.r. spectraare presented with the analytical results.J. M. VANPAASSCHEN et R. A. GEANANGEL. Can. J. Chem. 53.723 (1975). On a isole et caractkrisk les nouveaux composes triethylknediamine-BH2F, -BHFz, -BFJ, piperazine-BHzF, -BHF2 et -BFJ; ces complexes sont obtenus en faisant reagir les diamines approprikes sur le complexe trimethylamine-fluoroborane. L'utilisation de cette methode conduit uniquement aux adduits du monoborane sur les amines difonctionnelles. On rationnalise la stabilite de ces adduits de monoboranc en se basant sur un point de vue mecanistique. En plusdes donnees analytiques, on rapporte les spectres r.m.n. du proton et du bore 11 e t les spectres i.r.[Traduit par le journal]

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Section: Methodssupporting

confidence: 65%

Preparation of the Piperazine– and Triethylenediamine–Monoborane Adducts of BH₃, BH₂F, BHF₂, and BF₃

Vanpaasschen¹,

Geanangel²

1975

Can. J. Chem.

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“…It should be noted that the amount of released hydrogen cannot be explained by the degree of polymerization. We assigned the peak at 139.1238 to the imidazolium cation by the mass of imidazolium cation calculated for C 8 10 and more than that reported by Sahler et al 15 Thus, we claim that the dehydrogenation process in a vacuum facilitates the creation of milder condition. 9.…”

Section: Hr-msmentioning

confidence: 51%

Quantum chemical and experimental insights for the ionic liquid facilitated thermal dehydrogenation of ethylene diamine bisborane

et al. 2015

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The current work reports the judicial selection and subsequent dehydrogenation reaction with ionic liquid (IL) facilitated ethylene diamine bisborane (EDAB). Quantum chemical based COSMO-SAC (COnductor like Screening MOdel Segment Activity Coefficient) model was initially used to screen the ILs as available from Sigma Aldrich. LUMO-HOMO calculation was then performed to analyze the stability of EDAB/IL complexes. The molecular modeling studies converged on the two ILs, namely 1-ethyl-3-methyl imidazolium acetate ([EMIM][OAc]) and 1-butyl-3-methyl imidazolium acetate ([BMIM][OAc]), which were subsequently chosen for the dehydrogenation experiments. The thermal dehydrogenation of EDAB was carried out at 95 C and 105 C under vacuum so as to prevent generation of oxygen moieties. A total of 3.96 and 3.52 equivalents of hydrogen were released from the desorption of EDAB/[BMIM][OAc] and EDAB/[EMIM][OAc], respectively, at 105 C. The purity of released gas was confirmed by gas chromatographic analysis, while the catalytic activity of ILs was confirmed by 1 H NMR characterization of pure EDAB, ILs and EDAB/IL complexes both before and after the reaction. 11 B NMR analysis confirms the presence of trigonal boron (sp 2 ) BH 2 group as the only hydrogen containing boron moiety in dehydrogenated EDAB. Further, the two-stage release mechanism of EDAB was also verified by thermogravimetric analysis. High resolution mass spectrometry was able to detect the mass of cyclic repeat units in the polymeric chain containing an sp 2 BH 2 group. † Electronic supplementary information (ESI) available: The COSMO-SAC parameters and the sigma proles of EDAB, imidazolium cations and acetate anions. Further it also depicts the HOMO-LUMO energy gap of EDAB, [EMIM] [OAc] and [BMIM][OAc]. SeeFig. 8 Plot for 11 B NMR. (a) EDAB/[BMIM][OAc] before reaction, (b) EDAB/[BMIM][OAc] after reaction.This journal is

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“…In this work, we investigate the high temperature pyrolytic decomposition of a different amine-borane adduct, namely ethane 1,2-diamineborane (BH 3 NH 2 CH 2 CH 2 NH 2 BH 3 , EDAB hereafter). The synthesis of this compound was reported in the early 1960s through two paths, and its structural and vibrational properties were also investigated [ 13 , 14 , 15 ]. However, the thermolysis of EDAB has not been reported until recently.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Ternary Borocarbonitrides by High Temperature Pyrolysis of Ethane 1,2-Diamineborane

et al. 2015

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Ethane 1,2-diamineborane (EDAB) is an alkyl-containing amine-borane adduct with improved hydrogen desorption properties as compared to ammonia borane. In this work, it is reported the high temperature thermolytic decomposition of EDAB. Thermolysis of EDAB has been investigated by concomitant thermogravimetry-differential thermal analysis-mass spectrometry experiments. EDAB shows up to four H2 desorption events below 1000 °C. Small fractions of CH4, C2H4 and CO/CO2 are also observed at moderate-high temperatures. The solid-state thermolysis product has been characterized by means of different structural and chemical methods, such as X-ray diffraction, Raman spectroscopy, Scanning electron microscopy, Elemental analysis, and X-ray photoelectron spectroscopy (XPS). The obtained results indicate the formation of a ternary borocarbonitride compound with a poorly-crystalline graphitic-like structure. By contrast, XPS measurements show that the surface is rich in carbon and nitrogen oxides, which is quite different to the bulk of the material.

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Ethane 1,2-Diamineborane

Cited by 39 publications

References 0 publications

Preparation of the Piperazine– and Triethylenediamine–Monoborane Adducts of BH₃, BH₂F, BHF₂, and BF₃

Preparation of the Piperazine– and Triethylenediamine–Monoborane Adducts of BH₃, BH₂F, BHF₂, and BF₃

Quantum chemical and experimental insights for the ionic liquid facilitated thermal dehydrogenation of ethylene diamine bisborane

Synthesis of Ternary Borocarbonitrides by High Temperature Pyrolysis of Ethane 1,2-Diamineborane

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Ethane 1,2-Diamineborane

Cited by 39 publications

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Preparation of the Piperazine– and Triethylenediamine–Monoborane Adducts of BH3, BH2F, BHF2, and BF3

Preparation of the Piperazine– and Triethylenediamine–Monoborane Adducts of BH3, BH2F, BHF2, and BF3

Quantum chemical and experimental insights for the ionic liquid facilitated thermal dehydrogenation of ethylene diamine bisborane

Synthesis of Ternary Borocarbonitrides by High Temperature Pyrolysis of Ethane 1,2-Diamineborane

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Preparation of the Piperazine– and Triethylenediamine–Monoborane Adducts of BH₃, BH₂F, BHF₂, and BF₃

Preparation of the Piperazine– and Triethylenediamine–Monoborane Adducts of BH₃, BH₂F, BHF₂, and BF₃