維基百科

4-(二甲基氨基)苯基五唑

化合物

4-(二甲基氨基)苯基五唑，是一個不穩定的、有爆炸性的化合物，它包含了非常罕見的由五個氮原子組成的五唑環。苯環對位上的二甲基氨基的給電子效應使得此化合物比苯基五唑更穩定。在室溫下，其化學半衰期只有幾個小時，然而在超低溫下儲存是可能的。這個化合物在1956年[1][2][3]與其他取代的芳基五唑一起被初次製備出來。對各種其他的衍生物的研究也在進行，但必定由於這些化合物的不穩定性而受到限制。[4][5][6][7][8] 一些取代基更多的衍生物，如 2,6-二羥基-4-(二甲基氨基)苯基五唑，要稍微更穩定一些，但是反過來，製備這些衍生物的難度更大。[9][10]目前的研究聚焦於形成這些五唑衍生物的過渡金屬配合物，因為五唑環可能由於與金屬中心的化學鍵而穩定下來。[11][12][13]

4-(二甲基氨基)苯基五唑
IUPAC名
4-(二甲基氨基)苯基五唑
識別
CAS號 58402-54-3  checkY
PubChem 23279314
ChemSpider 10447638
SMILES
 
  • n1nnnn1-c2ccc(N(C)C)cc2
性質
化學式 C8H10N6
摩爾質量 190.205 g·mol⁻¹
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

參考文獻

  1. ^ Huisgen R, I. Ugi. Zur Losung eines klassichen Problems der organischen Stickstoff-Chemie. Angewandte Chemie. 1956; 68:705-706.
  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. ^ Butler, Richard N.; Collier, Seamus; Fleming, Adrienne F. M. 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 (Royal Society of Chemistry (RSC)). 1996, (5): 801. ISSN 0300-9580. doi:10.1039/p29960000801. 
  6. ^ Butler, Richard N.; Fox, Anthony; Collier, Seamus; Burke, Luke A. 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 (Royal Society of Chemistry (RSC)). 1998, (10): 2243–2248. ISSN 0300-9580. doi:10.1039/a804040k. 
  7. ^ Benin V, Kaszynski P, Radziszewski JG. Arylpentazoles revisited: experimental and theoretical studies of 4-hydroxyphenylpentazole and 4-oxophenylpentazole anion. The Journal of Organic Chemistry. February 2002, 67 (4): 1354–8. PMID 11846686. doi:10.1021/jo0110754. 
  8. ^ Carlqvist, Peter; Östmark, Henrik; Brinck, Tore. The Stability of Arylpentazoles. The Journal of Physical Chemistry A (American Chemical Society (ACS)). 2004, 108 (36): 7463–7467. ISSN 1089-5639. doi:10.1021/jp0484480. 
  9. ^ Efforts to synthesize the pentazolate anion [1][永久失效連結]
  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 [2] （頁面存檔備份，存於網際網路檔案館）
  11. ^ Tsipis AC, Chaviara AT. Structure, energetics, and bonding of first row transition metal pentazolato complexes: a DFT study. Inorganic Chemistry. February 2004, 43 (4): 1273–86. PMID 14966962. doi:10.1021/ic035112g. 
  12. ^ Burke, Luke A.; Fazen, Paul J. 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)4ClN5. Chemical Communications (Royal Society of Chemistry (RSC)). 2004, (9): 1082. ISSN 1359-7345. doi:10.1039/b315812h. 
  13. ^ Burke, Luke A.; Fazen, Paul J. 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 (Wiley-Blackwell). 2009, 109 (15): 3613–3618. ISSN 0020-7608. doi:10.1002/qua.22408. 
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