Lophine

Last updated
Lophine
Lophine.svg
Names
Other names
2,4,5-triphenylimidazole
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.006.915 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-606-6
PubChem CID
UNII
  • InChI=1S/C21H16N2/c1-4-10-16(11-5-1)19-20(17-12-6-2-7-13-17)23-21(22-19)18-14-8-3-9-15-18/h1-15H,(H,22,23)
    Key: RNIPJYFZGXJSDD-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C2=C(N=C(N2)C3=CC=CC=C3)C4=CC=CC=C4
Properties
C21H16N2
Molar mass 296.373 g·mol−1
Appearancewhite solid
Density 1,0874 g/cm3
Melting point 275 °C (527 °F; 548 K)
Hazards
GHS labelling:
GHS-pictogram-skull.svg
Danger
H301
P264, P270, P301+P316, P321, P330, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lophine is the organic compound with the formula (C6H5C)2N2HCC6H5. 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. ↑ Radziszewski, B. R. (1877). "Untersuchungen über Hydrobenzamid, Amarin und Lophin". Berichte der Deutschen Chemischen Gesellschaft. 10: 70–75. doi:10.1002/cber.18770100122.
  2. ↑ Nakashima, Kenichiro (2003). "Lophine derivatives as versatile analytical tools". Biomedical Chromatography. 17 (2–3): 83–95. doi:10.1002/bmc.226. PMID   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. doi:10.1016/j.jorganchem.2005.10.040. ISSN   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. 41: 323–329. doi:10.1039/CT8824100323. ISSN   0368-1645.
  5. ↑ 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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