4-Dimethylaminophenylpentazole

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{{Chembox

| verifiedrevid = 477221554

| ImageFile = 4-Dimethylaminophenylpentazole.svg

| ImageSize = 180px

| ImageFile1 = 4-Dimethylaminophenylpentazole-3D-spacefill.png

| ImageSize1 = 200

| ImageAlt1 = 4-Dimethylaminophenylpentazole molecule

| PIN = N,N-Dimethyl-4-(1H-pentazol-1-yl)aniline

| OtherNames =

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 10447638

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C8H10N6/c1-13(2)7-3-5-8(6-4-7)14-11-9-10-12-14/h3-6H,1-2H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OICBARXSRMXZPL-UHFFFAOYSA-N

| SMILES1 = CN(C)c1ccc(cc1)n2nnnn2

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 58402-54-3

| PubChem = 23279314

| SMILES = n1nnnn1-c2ccc(N(C)C)cc2

}}

|Section2={{Chembox Properties

| C=8 | H=10 | N=6

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4-Dimethylaminophenylpentazole is an unstable, explosive compound that contains the rare pentazole ring, which is composed of five nitrogen atoms. The electron donating effect of the 4-dimethylamino substituent on the phenyl ring makes this compound one of the more stable of the phenylpentazoles. At room temperature, its chemical half-life is only a few hours, although storage is possible at cryogenic temperatures. The compound was first prepared in 1956{{cite journal | author = Huisgen R, I. Ugi | title = Zur Losung eines klassichen Problems der organischen Stickstoff-Chemie | journal = Angewandte Chemie | date = 1956 | volume = 68 | issue = 22 | pages = 705–706 | doi = 10.1002/ange.19560682212 | bibcode = 1956AngCh..68..705H }}{{cite journal | author = Ugi I, R. Huisgen | title = Pentazole II. Die Zerfallsgeschwindigkeit der Arylpentazole | journal = Chemische Berichte | date = 1958 | volume = 91 | issue = 3 | pages = 531–537 | doi = 10.1002/cber.19580910310}}Ugi I, Perlinger H, Perlinger L. Pentazole III. Kristallisierte Aryl-pentazole. Chemische Berichte 1958; 98:2324-2329, along with other substituted phenylpentazoles. Studies have been conducted on various other derivatives, though necessarily limited by the instability of these compounds.{{cite journal | author = John D. Wallis and Jack D. Dunitz | title = An all-nitrogen aromatic ring system: structural study of 4-dimethyl-aminophenylpentazole | journal = Journal of the Chemical Society, Chemical Communications | date = 1983 | pages = 910–911 }}{{Cite journal | doi = 10.1039/P29960000801 | last1 = Butler | first1 = R. N. | last2 = Collier | first2 = S. | last3 = Fleming | first3 = A. F. M. | title = Pentazoles: proton and carbon-13 NMR spectra of some 1-arylpentazoles: kinetics and mechanism of degradation of the arylpentazole system | journal = Journal of the Chemical Society, Perkin Transactions 2 | issue = 5 | pages = 801 | year = 1996}}{{Cite journal | doi = 10.1039/A804040K | last1 = Butler | first1 = R. N. | last2 = Fox | first2 = A. | last3 = Collier | first3 = S. | last4 = Burke | first4 = L. A. | title = 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 = Journal of the Chemical Society, Perkin Transactions 2 | issue = 10 | pages = 2243–2248 | year = 1998}}{{cite journal |vauthors=Benin V, Kaszynski P, Radziszewski JG |title=Arylpentazoles revisited: experimental and theoretical studies of 4-hydroxyphenylpentazole and 4-oxophenylpentazole anion |journal=The Journal of Organic Chemistry |volume=67 |issue=4 |pages=1354–8 |date=February 2002 |pmid=11846686 |doi=10.1021/jo0110754 }}{{Cite journal | doi = 10.1021/jp0484480 | last1 = Carlqvist | first1 = P. | last2 = Östmark | first2 = H. | last3 = Brinck | first3 = T. | title = The Stability of Arylpentazoles | journal = The Journal of Physical Chemistry A | volume = 108 | issue = 36 | pages = 7463 | year = 2004| bibcode = 2004JPCA..108.7463C }} Some more highly substituted derivatives, such as 2,6-dihydroxy-4-dimethylaminophenylpentazole, are slightly more stable but conversely, more difficult to make.{{cite web | url = https://www.foi.se/rest-api/report/FOI-R--1602--SE | title = Efforts to synthesize the pentazolate anion }}{{citation | author = David Adam | title = The synthesis and characterisation of halogen and nitro phenyl azide derivatives as highly energetic materials. PhD dissertation | publisher = Ludwig-Maximilans-Universität München | date = 2001 | url = http://edoc.ub.uni-muenchen.de/184/1/Adam_David.pdf }} Current research has focused on forming transition metal complexes of these pentazole derivatives, as the pentazole ring should be stabilised by bonding to the metal centre.{{cite journal |vauthors=Tsipis AC, Chaviara AT |title=Structure, energetics, and bonding of first row transition metal pentazolato complexes: a DFT study |journal=Inorganic Chemistry |volume=43 |issue=4 |pages=1273–86 |date=February 2004 |pmid=14966962 |doi=10.1021/ic035112g }}{{cite journal | last1 = Burke| year = 2004 | first1 = L. A. | last2 = Fazen | first2 = P. J.| title =Electronic Supplementary Information for Chemical Communications| journal = Chemical Communications| issue = 9 | pages = 1082–3 | doi = 10.1039/B315812H | pmid = 15116195 }}{{cite journal | last1 = Burke | first1 = L. A. | last2 = Fazen | first2 = P. J. | year = 2009 | title = Correlation analysis of the interconversion and nitrogen loss reactions of aryl pentazenes and pentazoles derived from aryl diazonium and azide ions | journal = International Journal of Quantum Chemistry | volume = 109 | issue = 15 | pages = 3613 | bibcode = 2009IJQC..109.3613B | doi = 10.1002/qua.22408}}