Lophine Explained

Lophine is the organic compound with the formula . 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

1. 10.1002/cber.18770100122 . Untersuchungen über Hydrobenzamid, Amarin und Lophin . 1877 . Radziszewski . B. R. . Berichte der Deutschen Chemischen Gesellschaft . 10 . 70–75 .
2. 10.1002/bmc.226 . Lophine derivatives as versatile analytical tools . 2003 . Nakashima . Kenichiro . Biomedical Chromatography . 17 . 2–3 . 83–95 . 12717796 .
3. 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 . 10.1016/j.jorganchem.2005.10.040 . 0022-328X.
4. Japp . Francis R. . Robinson . H. H. . 1882-01-01 . L.—On the constitution of amarine and lophine . Journal of the Chemical Society, Transactions . en . 41 . 0 . 323–329 . 10.1039/CT8824100323 . 0368-1645.
5. 10.1002/jhet.4771 . Catalyst-free one-pot synthesis of 2,4,5-tri- and 1,2,4,5-tetrasubstituted imidazoles . 2024 . Bandivadekar . Priyanka V. . Chaturbhuj . Ganesh U. . Journal of Heterocyclic Chemistry . 61 . 3 . 430–438 .