4-Dimethylaminophenylpentazole

4-Dimethylaminophenylpentazole is an unstable, [7] Benin V, Kaszynski P, Radziszewski JG (February

2002). Arylpentazoles revisited: experimental and
explosive compound that contains the rare pentazole ring,
theoretical studies of 4-hydroxyphenylpentazole and 4which is composed of ve nitrogen atoms. The electron
oxophenylpentazole anion. The Journal of Organic
donating eect of the 4-dimethylamino substituent on
Chemistry 67 (4): 13548. doi:10.1021/jo0110754.
the phenyl ring makes this compound one of the more
PMID 11846686.
stable of the phenylpentazoles. At room temperature, its
chemical half-life is only a few hours, although storage [8] Carlqvist, P.; stmark, H.; Brinck, T. (2004). The Stais possible at cryogenic temperatures. The compound
bility of Arylpentazoles. The Journal of Physical Chemwas rst prepared in 1956[1][2][3] along with other
istry A 108 (36): 7463. doi:10.1021/jp0484480.
substituted phenylpentazoles. Studies have been con[9] Eorts to synthesize the pentazolate anion
ducted on various other derivatives, though necessarily
[4][5][6][7][8]
limited by the instability of these compounds.
[10] David Adam. The synthesis and characterisation of haloSome more highly substituted derivatives, such as 2,6gen and nitro phenyl azide derivatives as highly enerdihydroxy-4-dimethylaminophenylpentazole, are slightly
getic materials. PhD dissertation, Ludwig-MaximilansUniversitt Mnchen, 2001
more stable but conversely, more dicult to make.[9][10]
Current research has focused on forming transition
[11] Tsipis AC, Chaviara AT (February 2004). Structure, enmetal complexes of these pentazole derivatives, as the
ergetics, and bonding of rst row transition metal penpentazole ring should be stabilised by bonding to the
tazolato complexes: a DFT study. Inorganic Chemmetal centre.[11][12][13]
istry 43 (4): 127386. doi:10.1021/ic035112g. PMID
14966962.

[12] Burke, L. A.; Fazen, P. J. (2004). Consideration of

spin states in determining the structure and decomposition of the transition metal pentazoles FeClN5, Fe(N5)2,
Fe(H2O)4ClN5, and Fe(NH3)4ClN5Electronic supplementary information (ESI) available: energies for all
structures with the various basis sets. See http://www.rsc.
org/suppdata/cc/b3/b315812h/". Chemical Communications (9): 1082. doi:10.1039/B315812H.

References

[1] Huisgen R, I. Ugi. Zur Losung eines klassichen Problems

der organischen Sticksto-Chemie. Angewandte Chemie.
1956; 68:705-706.
[2] Ugi I, R. Huisgen.
Pentazole II. Die Zerfallsgeschwindigkeit der Arylpentazole. Chemische Berichte.
1958; 91:531-537.

[13] Burke, L. A.; Fazen, P. J. (2009). Correlation analysis

of the interconversion and nitrogen loss reactions of aryl
pentazenes and pentazoles derived from aryl diazonium
and azide ions. International Journal of Quantum Chemistry 109 (15): 3613. Bibcode:2009IJQC..109.3613B.
doi:10.1002/qua.22408.

[3] Ugi I, Perlinger H, Perlinger L. Pentazole III.

Kristallisierte Aryl-pentazole.
Chemische Berichte
1958; 98:2324-2329,
[4] John D. Wallis and Jack D. Dunitz. An all-nitrogen
aromatic ring system: structural study of 4-dimethylaminophenylpentazole. Journal of the Chemical Society.
Chemical Communications. 1983: 910-911.
[5] Butler, R. N.; Collier, S.; Fleming, A. F. M. (1996).
Pentazoles: proton and carbon-13 NMR spectra of
some 1-arylpentazoles: kinetics and mechanism of
degradation of the arylpentazole system. Journal of
the Chemical Society, Perkin Transactions 2 (5): 801.
doi:10.1039/P29960000801.
[6] Butler, R. N.; Fox, A.; Collier, S.; Burke, L. A. (1998).
Pentazole chemistry: the mechanism of the reaction of
aryldiazonium chlorides with azide ion at 80 C: concerted versus stepwise formation of arylpentazoles, detection of a pentazene intermediate, a combined 1H and 15N
NMR experimental and ab initio theoretical study. Journal of the Chemical Society, Perkin Transactions 2 (10):
2243. doi:10.1039/A804040K.

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