A Computational Study on the Mechanism and Kinetics of the Pyrolysis of 2-Nitrophenyl Azide

Rauhut, Guntram; Eckert, Frank

doi:10.1021/jp991181y

Cited by 38 publications

(18 citation statements)

References 44 publications

(103 reference statements)

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“…This reaction sequence was demonstrated nearly 100 years ago 309. An electrocyclic mechanism is assumed306b, 308 in which, in a few cases, subsequent aromatization occurs through an H or alkyl shift. This applies especially to the 2 H ‐indoles and 2 H ‐benzimidazoles.…”

Section: Reactions Of Organic Azidesmentioning

confidence: 99%

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

et al. 2005

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Since the discovery of organic azides by Peter Griess more than 140 years ago, numerous syntheses of these energy-rich molecules have been developed. In more recent times in particular, completely new perspectives have been developed for their use in peptide chemistry, combinatorial chemistry, and heterocyclic synthesis. Organic azides have assumed an important position at the interface between chemistry, biology, medicine, and materials science. In this Review, the fundamental characteristics of azide chemistry and current developments are presented. The focus will be placed on cycloadditions (Huisgen reaction), aza ylide chemistry, and the synthesis of heterocycles. Further reactions such as the aza-Wittig reaction, the Sundberg rearrangement, the Staudinger ligation, the Boyer and Boyer-Aubé rearrangements, the Curtius rearrangement, the Schmidt rearrangement, and the Hemetsberger rearrangement bear witness to the versatility of modern azide chemistry.

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Section: Reactions Of Organic Azidesmentioning

confidence: 99%

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

et al. 2005

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“…Diese Reaktionsfolge wurde schon vor fast 100 Jahren beschrieben 309. Man geht von einem elektrocyclischen Mechanismus aus,306b, 308 wobei es in einigen Fällen zu nachfolgender Aromatisierung durch eine H‐ oder Alkyl‐Wanderung kommt. Das gilt insbesondere für die 2 H ‐Indole und 2 H ‐Benzimidazole.…”

Section: Reaktionen Organischer Azideunclassified

Organische Azide – explodierende Vielfalt bei einer einzigartigen Substanzklasse

et al. 2005

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Seit der Entdeckung der organischen Azide vor über einhundertvierzig Jahren durch Peter Grieß wurde eine Reihe von Synthesen für diese energiereichen Moleküle entwickelt. In letzter Zeit haben sich völlig neue Perspektiven durch Anwendungen in der Peptidchemie, der kombinatorischen Chemie und der Heterocyclensynthese ergeben. Auf dem interdisziplinären Gebiet zwischen Chemie, Biologie, Medizin und Materialwissenschaften nehmen organische Azide inzwischen einen wichtigen Raum ein. In diesem Aufsatz werden die Grundzüge der Azid‐Chemie dargelegt und aktuelle Entwicklungen auf diesem Gebiet beleuchtet. Der Schwerpunkt liegt dabei auf Cycloadditionen (Huisgen‐Reaktion), Aza‐Ylidchemie und der Synthese von Heterocyclen. Weitere Reaktionen wie die Aza‐Wittig‐Reaktion, Sundberg‐Umlagerung, Staudinger‐Ligation, Boyer‐ und Boyer‐Aubé‐Umlagerung, Curtius‐Umlagerung, Schmidt‐Umlagerung sowie die Hemetsberger‐Umlagerung zeugen von der Vielfältigkeit moderner Azid‐Chemie.

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“…The very high reactivity and the application of organoazides in synthetic chemistry and many important industries [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36] has drawn the attention to investigate the structure and conformational behavior of vinyl azide, CH2=CH-NNN [37] and formyl azide, CHO-NNN [38], by DFT and ab initio MP2 calculations. Both molecules were predicted to have a cis/trans conformational equilibrium with the gauche form being the transition state.…”

Section: Introductionmentioning

confidence: 99%

Structural Stability and Vibrational Analyses of Haloselenonyl Azides, XSeO2-NNN, where X is F, Cl, Br

Förner

Badawi

Seddigi

2005

IJMS

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Abstract:The structural stability of haloselenonyl azides was investigated by quantum mechanical Møller-Plesset perturbation theory of second order and density functional theory calculations. The 6-311+G** basis set was used to include polarization and diffuse functions in the calculations at the DFT-B3LYP level. The potential scans for the rotation of the -NNN rotor were calculated and found to be consistent with a single minimum that corresponds to a gauche conformation (-NNN moiety nearly eclipses one of the two selenonyl Se=O bonds) for the three halogens at ambient temperature. The structural parameters for the minima calculated by MP2 and DFT turned out to be very similar. The vibrational modes, infrared and Raman intensities as well as depolarization ratios were calculated at DFT-B3LYP/6-311+G** level for the three molecules in their gauche conformations. The potential energy distributions among symmetry coordinates of the normal modes of the molecules in their gauche conformation were then computed from normal coordinate analyses.

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A Computational Study on the Mechanism and Kinetics of the Pyrolysis of 2-Nitrophenyl Azide

Cited by 38 publications

References 44 publications

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

Organische Azide – explodierende Vielfalt bei einer einzigartigen Substanzklasse

Structural Stability and Vibrational Analyses of Haloselenonyl Azides, XSeO2-NNN, where X is F, Cl, Br

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