Tetracenes

The tetracenes are an inorganic group of substances. These are monounsaturated compounds with a chain of four nitrogen atoms bonded to one another . They are thermally unstable . A total of eleven N ₄ H ₄ isomers are known.

Overview

There are numerous isomers for the substance groups of the tetracenes. Some important ones are listed here with their properties:

Tetracenes
Surname	1-tetrazene	cis -2 tetrazene	trans -2-tetrazene
other names		( Z ) -2-tetrazene	( E ) -2-tetrazene
Structural formula
CAS number	14097-21-3	69996-02-7	54410-57-0
CAS number	27120-23-6
PubChem			5463295
Molecular formula	H ₄ N ₄
Molar mass	60.06 g mol ⁻¹
Physical state
Brief description			colorless solid (at −78 ° C)
density			1.4 g cm ⁻³

Likelihood of confusion

Tetrazene can easily be confused with tetracene (naphthacene) or the group of tetrazines .

Extraction and presentation

Organic derivatives of 1-tetrazene can be obtained by reacting diazonium salts with hydrazines which are substituted on a nitrogen atom.

The trans isomer of 2-tetrazene can be obtained in 90% yield by protolysis of trans-tetrakis (trimethylsilyl) tetraz-2-ene with a stoichiometric amount of trifluoroacetic acid in dichloromethane at 195 K.

properties

2-Tetrazene (H ₂ N-N = N-NH ₂ ) was manufactured in 1975 by Nils Wiberg . Its exact structure was established as trans -2-tetrazene by photoelectron spectroscopy.

At −78 ° C, 2-tetrazene is a colorless, solid substance that is sparingly soluble in methylene chloride . At approx. 0 ° C, 75% of it decomposes into nitrogen and hydrazine and 25% isomerizes to ammonium azide .

The trans isomer has a triclinic crystal structure with the space group P 1 (space group no. 2) . Template: room group / 2

A derivative of 1-tetrazene (HN = N − NH − NH ₂ ) is e.g. B. the initial explosive tetrazene . The compound itself has not yet been synthesized.

Tetrazoles

The tetrazoles are cyclic , diunsaturated derivatives of the tetracenes .

swell

Nils Wiberg , Heiner Bayer, Heinz Bachhuber: Isolation of Tetrazen, N4H4, Angewandte Chemie , 87th year 1975, No. 6, pages 202-203, doi : 10.1002 / anie.19750870611
Entry to tetracenes. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.

Individual evidence

↑ Lai-Cai Li, Jing Shang, Jun-Ling Liu, Xin Wang, Ning-Bew Wong: A G3B3 study of N4H4 isomers. In: Journal of Molecular Structure: THEOCHEM. 807, 2007, p. 207, doi : 10.1016 / j.theochem . 2006.12.009 .

↑ ^a ^b ^c ^d ^e Reinhard Haubold, Claudia Heinrich-Sterzel, Ulrike Ohms-Bredeman, Carol Strametz: N Nitrogen . Springer Science & Business Media, 2013, ISBN 978-3-662-06336-1 , p. 170 ( limited preview in Google Book search).

↑ Houben-Weyl Methods of Organic Chemistry Vol. E 16a, 4th Edition Supplement Organic N compounds I . Georg Thieme Verlag, 2014, ISBN 3-13-181904-9 , p. 1227 ( limited preview in Google Book search).

[DOI10.1016/j.theochem.2006.12.009-1] Lai-Cai Li, Jing Shang, Jun-Ling Liu, Xin Wang, Ning-Bew Wong: A G3B3 study of N4H4 isomers. In: Journal of Molecular Structure: THEOCHEM. 807, 2007, p. 207, doi : 10.1016 / j.theochem . 2006.12.009 .

[Reinhard_Haubold,_Claudia_Heinrich-Sterzel,_Ulrike_Ohms-Bredeman,_Carol_Strametz-2] Reinhard Haubold, Claudia Heinrich-Sterzel, Ulrike Ohms-Bredeman, Carol Strametz: N Nitrogen . Springer Science & Business Media, 2013, ISBN 978-3-662-06336-1 , p. 170 ( limited preview in Google Book search).

[3] Houben-Weyl Methods of Organic Chemistry Vol. E 16a, 4th Edition Supplement Organic N compounds I . Georg Thieme Verlag, 2014, ISBN 3-13-181904-9 , p. 1227 ( limited preview in Google Book search).