First Synthesis and Investigation of Two Hydroxyalkyl-Substituted 2-Tetrazenes

Porath, Bernd; Münzenberg, Ralf; Heymanns, P.; Rademacher, Paul; Boese, Roland; Bläser, Dieter; Latz, R.

doi:10.1002/(sici)1099-0690(199807)1998:7<1431::aid-ejoc1431>3.0.co;2-m

Cited by 11 publications

(6 citation statements)

References 45 publications

(25 reference statements)

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“…The silyl ether 27 was prepared according to a related method,23 and was purified by two successive distillations under reduced pressure. The organolithium 17 was prepared by deprotonation of N ‐Boc‐piperidine ( 16 ) using s BuLi, THF and TMEDA at −78 °C, then a solution of the silyl ether 27 (1 equiv) in THF was added (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

²H NMR Studies on Two‐Homopolypeptide Lyotropic Enantiodiscriminating Mesophases: Experimental Quantification of Solute–Fiber Affinities

Lesot

Lafon

Aroulanda

et al. 2008

Chemistry A European J

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The analytical potential and enantioselective properties of lyotropic mesophases made by mixing two chemically different chiral polypeptides are described. Here we examine the case of a mixture of poly-gamma-benzyl-L-glutamate (PBLG) and poly-epsilon-carbobenzyloxy-L-lysine (PCBLL). We demonstrate that 2H NMR spectroscopy on these chiral oriented mixtures can discriminate both enantiomers and enantiotopic directions in prochiral molecules. Moreover, in such systems, degree of enantiodiscrimination, resolution, and sensitivity can be conjointly optimized by changing the relative proportion of the two polypeptides. Therefore, these new enantiodiscriminating media provide a favorable alternative to single-polypeptide mesophases with respect to stereochemical applications. At a more fundamental level, the present work points out that solute distribution in the vicinity of each polypeptide partly governs the degree of enantiodiscrimination and NMR relaxation rates. To this end, the experimental trends of solute NMR observables (Delta nu Q, T1) versus the fraction of peptide units of each polymer were analyzed by using a "mean-field" model derived from that proposed for mixtures of thermotropic nematic solvents, and based on the separation of intermolecular interactions between the solute and both polypeptides. This approach allows the relative solute-fiber affinities in these lyotropic systems to be determined. To identify the factors controlling solute-polypeptide affinities, we investigated various solutes (polar/apolar, rigid/flexible, achiral/prochiral/chiral molecules) using 2H NMR at natural abundance or on isotopically enriched solutes.

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Section: Resultsmentioning

confidence: 99%

²H NMR Studies on Two‐Homopolypeptide Lyotropic Enantiodiscriminating Mesophases: Experimental Quantification of Solute–Fiber Affinities

Lesot

Lafon

Aroulanda

et al. 2008

Chemistry A European J

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“…+ cation methylated at N3 and N2, respectively). Note that the electronic energy calculated by Porath et al 16 for 1 (À378.59825990 a.u.) points at the protonation/methylation of 1 playing a stabilizing role.…”

Section: Synthesis and Stabilitymentioning

confidence: 94%

“…For this reason they are involved in both intra-and extra-molecular hydrogen-bonding. 16 The electron-rich character give them also a high intrinsic basicity (e.g., pK b (N 4 Et 4 ) = 5.12), 17 which increases with the larger the size of the substituent. The simplest NJC Dynamic Article Links www.rsc.org/njc PAPER 2-tetrazene possible, i.e., N 4 H 4 , (R = H) was synthesized as the trans-form by Wiberg and coworkers in 1975 over a four steps procedure starting from hydrazine.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and stability of 2-tetrazenium salts

Sabaté

Delalu

2011

New J. Chem.

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“…through N-NH 2 on the nitrogen heterocycle, 22,23 but the yields of the above methods for introducing azo bonds on the nitrogen atom of the triazole ring are relatively low. 22 Therefore, this work used Sodium Dichloro Iso Cyanurate (SDIC) to oxidatively couple 4-amino-1,2,4triazole to obtain 4,4′-azobis-1,2,4-triazole in higher-yield azoles. 24 The purpose of this study is to explore the relevant kinetic data of the thermal decomposition of ATRZ to provide a basis for future research on azo-energetic materials.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic Analysis and Pyrolysis Mechanism of 4,4′-Azobis-1,2,4-triazole

Qin,

Zhu,

Zhang

et al. 2023

ACS Omega

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The nonisothermal thermal decomposition kinetics of 4,4′-azobis-1,2,4-triazole (ATRZ) at different heating rates (5, 10, 15, and 20 °C·min–1) were investigated by thermogravimetry (TG) and differential scanning calorimetry (DSC) studies. The thermal decomposition kinetic parameters such as apparent activation energy (E) and pre-exponential factor (A) were calculated by the Kissinger, Ozawa, and Šatava-Šestak methods. The E and A values calculated by the above three methods are very close, which are 391.1 kJ·mol–1/1034.92 s–1, 381.1 kJ·mol–1/1034.30 s–1, and 393.4 kJ·mol–1/1035.76 s–1, respectively. Then, the decomposition mechanism function of ATRZ is analyzed by the calculated results. The results show that the decomposition temperature of ATRZ is about 300 °C and the exothermic decomposition speed is fast. The decomposition pathway of ATRZ was analyzed by pyrolysis-gas chromatography–mass spectrometry (PY-GC-MS). The thermal decomposition kinetic equation of the ATRZ was deduced.

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First Synthesis and Investigation of Two Hydroxyalkyl-Substituted 2-Tetrazenes

Cited by 11 publications

References 45 publications

²H NMR Studies on Two‐Homopolypeptide Lyotropic Enantiodiscriminating Mesophases: Experimental Quantification of Solute–Fiber Affinities

²H NMR Studies on Two‐Homopolypeptide Lyotropic Enantiodiscriminating Mesophases: Experimental Quantification of Solute–Fiber Affinities

Synthesis and stability of 2-tetrazenium salts

Thermodynamic Analysis and Pyrolysis Mechanism of 4,4′-Azobis-1,2,4-triazole

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First Synthesis and Investigation of Two Hydroxyalkyl-Substituted 2-Tetrazenes

Cited by 11 publications

References 45 publications

2H NMR Studies on Two‐Homopolypeptide Lyotropic Enantiodiscriminating Mesophases: Experimental Quantification of Solute–Fiber Affinities

2H NMR Studies on Two‐Homopolypeptide Lyotropic Enantiodiscriminating Mesophases: Experimental Quantification of Solute–Fiber Affinities

Synthesis and stability of 2-tetrazenium salts

Thermodynamic Analysis and Pyrolysis Mechanism of 4,4′-Azobis-1,2,4-triazole

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²H NMR Studies on Two‐Homopolypeptide Lyotropic Enantiodiscriminating Mesophases: Experimental Quantification of Solute–Fiber Affinities

²H NMR Studies on Two‐Homopolypeptide Lyotropic Enantiodiscriminating Mesophases: Experimental Quantification of Solute–Fiber Affinities