| 词条 | 4-Dimethylaminophenylpentazole |
| 释义 |
| verifiedrevid = 477221554 | ImageFile = 4-dimethylaminophenylpentazole.png | ImageSize = 180px | ImageFile1 = 4-Dimethylaminophenylpentazole-3D-spacefill.png | ImageSize1 = 200 | ImageAlt1 = 4-Dimethylaminophenylpentazole molecule | IUPACName = 4-dimethylaminophenylpentazole | 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|??}} | CASNo = | PubChem = 23279314 | SMILES = n1nnnn1-c2ccc(N(C)C)cc2 |Section2={{Chembox Properties | Formula = C8H10N6 | MolarMass = 190.205 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = |Section6={{Chembox Explosive | ShockSens = | FrictionSens = | DetonationV = }}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[1][2][3] along with other substituted phenylpentazoles. Studies have been conducted on various other derivatives, though necessarily limited by the instability of these compounds.[4][5][6][7][8] Some more highly substituted derivatives, such as 2,6-dihydroxy-4-dimethylaminophenylpentazole, are slightly more stable but conversely, more difficult to make.[9][10] 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.[11][12][13] References1. ^Huisgen R, I. Ugi. Zur Losung eines klassichen Problems der organischen Stickstoff-Chemie. Angewandte Chemie. 1956; 68:705-706. {{DEFAULTSORT:Dimethylaminophenylpentazole, 4-}}{{Explosive-stub}}2. ^Ugi I, R. Huisgen. Pentazole II. Die Zerfallsgeschwindigkeit der Arylpentazole. Chemische Berichte. 1958; 91:531-537. 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-dimethyl-aminophenylpentazole. Journal of the Chemical Society. Chemical Communications. 1983: 910-911. 5. ^{{Cite journal | doi = 10.1039/P29960000801 | last1 = Butler | first1 = R. N. | last2 = Collier | first2 = S. | isbn = | 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}} 6. ^{{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 | year = 1998}} 7. ^{{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 |url=}} 8. ^{{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 }} 9. ^Efforts to synthesize the pentazolate anion{{dead link|date=September 2016 |bot=InternetArchiveBot |fix-attempted=yes }} 10. ^David Adam. The synthesis and characterisation of halogen and nitro phenyl azide derivatives as highly energetic materials. PhD dissertation, Ludwig-Maximilans-Universität München, 2001 11. ^{{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 |url=}} 12. ^{{cite journal | author = | last1 = Burke| year = 2004 | first1 = L. A. | last2 = Fazen | first2 = P. J.| title =Electronic Supplementary Information for Chemical Communications| journal = Chemical Communications| volume = | issue = 9 | pages = 1082 | url = | format = | accessdate = | doi = 10.1039/B315812H }} 13. ^{{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}} 3 : Explosive chemicals|Pentazoles|Anilines |
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