Chemistry:Lophine
From HandWiki
Lophine is the organic compound with the formula (C
6H
5C)
2N
2HCC
6H
5. It is a derivative of imidazole wherein all three carbon atoms have phenyl groups as substituents. A white solid, this compound gave the first example of chemiluminescence when its basic solutions were exposed to air.[1] Its chemiluminescence continues to attract attention.[2]
Lophine and its dihydro analogue amarine (meso-2,4,5-triphenyl-2-imidazoline[3]) were discovered early in the history of organic chemistry (between 1841 and 1847),[4] before the development of a structural theory of organic chemistry by Kekulé and Couper in the 1850s. Lophine is prepared by condensation of benzaldehyde, benzil, and ammonia.[5]
References
- ↑ Radziszewski, B. R. (1877). "Untersuchungen über Hydrobenzamid, Amarin und Lophin". Berichte der Deutschen Chemischen Gesellschaft 10: 70–75. doi:10.1002/cber.18770100122. https://zenodo.org/record/1425132.
- ↑ Nakashima, Kenichiro (2003). "Lophine derivatives as versatile analytical tools". Biomedical Chromatography 17 (2–3): 83–95. doi:10.1002/bmc.226. PMID 12717796.
- ↑ Huang, Xue-Feng; Song, Yu-Mei; Wang, Xi-Sen; Pang, Jie; Zuo, Jing-Lin; Xiong, Ren-Gen (2006-02-15). "Crystal structures of amarine and isoamarine and copper(I) coordination chemistry with their allylation products". Journal of Organometallic Chemistry 691 (5): 1065–1074. doi:10.1016/j.jorganchem.2005.10.040. ISSN 0022-328X. https://www.sciencedirect.com/science/article/abs/pii/S0022328X05008788.
- ↑ Japp, Francis R.; Robinson, H. H. (1882-01-01). "L.—On the constitution of amarine and lophine" (in en). Journal of the Chemical Society, Transactions 41: 323–329. doi:10.1039/CT8824100323. ISSN 0368-1645. https://pubs.rsc.org/en/content/articlelanding/1882/ct/ct8824100323.
- ↑ Bandivadekar, Priyanka V.; Chaturbhuj, Ganesh U. (2024). "Catalyst-free one-pot synthesis of 2,4,5-tri- and 1,2,4,5-tetrasubstituted imidazoles". Journal of Heterocyclic Chemistry 61 (3): 430–438. doi:10.1002/jhet.4771.
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