The Chemistry of Nitrogen-rich Functional Groups

Nitrogen is unique among the non-carbon atoms in its ability to form single, double, and triple bonds with itself, giving rise to a wide range of organic-chemical groups containing several nitrogen atoms in different states and geometries. The present volume surveys the properties and chemical behaviour of all important nitrogen-rich organic-chemical groups, including azides, azimines, aziridines, diazo compounds, nitramines, nitrenes, nitrosamines, polyazine N-oxides, tetrazoles, triazanes, triazenes, and triazoles. A special focus lies on commercially important species which are used, e. g., as powerful explosives.

PATAI's Chemistry of Functional Groups publishes comprehensive reviews on all aspects of specific functional groups. Each volume contains outstanding surveys on theoretical and computational aspects, NMR, MS, other spectroscopic methods and analytical chemistry, structural aspects, thermochemistry, photochemistry, synthetic approaches and strategies, synthetic uses and applications in chemical and pharmaceutical industries, biological, biochemical and environmental aspects. To date, almost 150 volumes have been published in the series.Stickstoff besitzt unter Nichtkohlestoffatomen die einzigartige Fähigkeit, Ein-, Zwei- und Dreifachbindungen mit sich selbst zu bilden. Dadurch entsteht eine Vielzahl organo-chemischer Gruppen, die mehrere Stickstoffatome in verschiedenen Zuständen und Geometrien enthalten. Der vorliegende Band untersucht die Eigenschaften und das chemische Verhalten aller wichtigen kohlenstoffreichen organo-chemischen Gruppen wie Azide, Azimine, Aziridine, Diazoverbindungen, Nitramine, Nitrene, Nitrosamine, Polyazine-N-oxide, Tetrazole, Triazene und Triazole. Ein besonderer Fokus liegt auf ökonomisch wichtigen Verbindungen, die z. B. als hochwirksame Sprengstoffe zum Einsatz kommen.

In der Reihe PATAI's Chemistry of Functional Groups erscheinen umfassende Untersuchungen zu allen Aspekten spezieller funktionaler Gruppen. Jeder Band bietet einen herausragenden Überblick über theoretische Aspekte und rechnergestützte Verfahren, NMR, MS und weitere spektroskopische Methoden sowie über die analytische Chemie, strukturelle Aspekte, Thermochemie, Fotochemie, synthetische Ansätze und Strategien, synthetische Anwendungsbereiche und Anwendungen in der chemischen und pharmazeutischen Industrie, biologische, biochemische und Umweltaspekte. Bis heute wurden in der Reihe nahezu 150 Bände veröffentlicht.

1. Introduction to the energetics and thermochemical aspects of polynitrogen species 1
Suzanne W. Slayden, Alexander Greer, and Joel F. Liebman

2. Stable hydrazyls and push–pull (capto-dative) aminyl free radicals 17
Alexandru T. Balaban

3. New combinations of organic azides and adjacent functional groups 27
Klaus Banert

4. Bridged azobenzenes and their chemical applications 65
David J. Warner, Katie S. Keane, and Silas C. Blackstock

5. Click chemistry and nitrogen-containing heterocycles formed in surface functionalization reactions 115
Yuan Chen, Hao Fan, and Elena Galoppini

6. Triplet vinylnitrenes 161
Upasana Banerjee, Kosala Thenna-Hewa, and Anna D. Gudmundsdottir

7. Nitrogen catenation: polyazoles and polyazines 199
Peter Politzer and Jane S. Murray

8. N-Oxides of polyazoles and polyazines 231
Peter Politzer and Jane S. Murray

9. Bridged azobenzenes and their biological applications 251
David J. Warner, Katie S. Keane, Carl Jacky Saint-Louis, and Silas C. Blackstock

10. Thermochemical insights on small nitrogen heterocyclic compounds 287
Vera L. S. Freitas and Maria D. M. C. Ribeiro da Silva

11. Some thermochemical aspects of acyclic polynitrogen species 329
Suzanne W. Slayden, Alexander Greer, and Joel F. Liebman

12. The Brønsted acid/base character of the N−N and N=N bonds 357
John E. Bartmess

Subject index 385

Professor Alexander Greer, Department of Chemistry, Brooklyn College, The City University of New York, New York, USA.

Professor Joel F. Liebman, Department of Chemistry & Biochemistry, University of Maryland (UMBC), Baltimore, USA.

PATAI's Chemistry of Functional Groups The Chemistry of Nitrogen-rich Functional Groups

A series of advanced treatises founded by Professor Saul Patai and now under the general editorship of Professors Zvi Rappoport, Joel F. Liebman and Ilan Marek

PATAI's Chemistry of Functional Groups publishes comprehensive reviews on all aspects of specific functional groups. Each volume contains outstanding surveys on theoretical and computational aspects, NMR, MS, other spectroscopic methods and analytical chemistry, structural aspects, thermochemistry, photochemistry, synthetic approaches and strategies, synthetic uses and applications in chemical and pharmaceutical industries, biological, biochemical, and environmental aspects. To date, over 140 volumes have been published in the series.