介离子化合物
介离子化合物是指结构上同时有正负双偶极的五、六元杂环化合物，并且其负电荷和正电荷都处于离域状态。介离子化合物无法用电中性的共价结构表示，也无法用一个共振式就准确地表示，为了与两性离子化合物作区分，引入了介离子的概念[1][2]。较出名的介离子化合物有悉尼酮、悉尼酮亚胺（例如兴奋剂美索卡伯）、慕尼黑酮、三氟苯嘧啶类杀虫剂和介离子卡宾等。有研究将介离子化合物称作介离子杂环甜菜碱[3]。
参考文献
脚注
- ^ Ollis, W.David; Ramsden, Christopher A. Meso-ionic Compounds. Adv. Heterocycl. Chem. 1976, 19 (1).
- ^ 国际纯化学和应用化学联合会，化学术语概略，第二版。（金皮书）(1997)。在线校正版: (2006–) "mesoionic compounds"。doi:10.1351/goldbook.M03842
- ^ Ollis, W.David; Stanforth, Stepher P.; Ramsden, Christopher A. Heterocyclic mesomeric betaines. Tetrahedron. 1985, 41 (12): 2239–2329. doi:10.1016/S0040-4020(01)96625-6.
参考书目
- Senff-Ribeiro, A; Echevarria, A; Silva, EF; Franco, CR; Veiga, SS; Oliveira, MB. Cytotoxic effect of a new 1,3,4-thiadiazolium mesoionic compound (MI-D) on cell lines of human melanoma. British Journal of Cancer. 2004, 91 (2): 297–304. PMC 2409799
. PMID 15199390. doi:10.1038/sj.bjc.6601946. - Mickleburgh, I; Geng, F; Tiley, L. Mesoionic heterocyclic compounds as candidate messenger RNA cap analogue inhibitors of the influenza virus RNA polymerase cap-binding activity. Antiviral Chemistry & Chemotherapy. 2009, 19 (5): 213–8. PMID 19483269. doi:10.1177/095632020901900504.
- Cadena, Silvia M.S.C.; Carnieri, Eva G.S.; Echevarria, Aurea; De Oliveira, Maria Benigna Martinelli. Interference of MI-D, a new mesoionic compound, on artificial and native membranes. Cell Biochemistry and Function. 2002, 20 (1): 31–7. PMID 11835268. doi:10.1002/cbf.932.
- Papageorgiou, M.; Kokkou, S. C.; Rentzeperis, P. J.; Tsoleridis, C. Structure of the mesoionic compound N-[1-methyl-3-(p-tolyl)-4-(1,2,3-triazolio)]acetamidate (MMTAT), C12H14N4O. Acta Crystallographica Section C. 1983, 39 (11): 1581–1583. doi:10.1107/S0108270183009348.
- Potts, K. T.; Husain, Syeda. Mesoionic compounds. XIV. Mesoionic compounds of the imidazole series. The Journal of Organic Chemistry. 1971, 36 (22): 3368–3372. doi:10.1021/jo00821a022.
