Sokhna, Seynabou, Seck, Insa, Thiam, Ibrahima El Hadj, Presset, Marc, Ndoye, Samba Fama, Ba, Lalla Aïcha, Samb, Issa, Coles, Simon J., Orton, James, Seck, Matar, Le Gall, Erwan and Gaye, Mohamed (2023) Syntheses and crystal structure of 4-[(pyridin-3-yl)diazenyl]morpholine and 1-[(pyridin-3-yl)diazenyl]-1,2,3,4-tetrahydroquinoline. Acta Crystallographica Section E: Crystallographic Communications, E79, 74-78. (doi:10.1107/S2056989023000129).
Abstract
Two new heterocyclic 1,2,3-triazenes were synthesized by diazotation of 3-aminopyridine following respectively by coupling with morpholine or 1,2,3,4-tetrahydroquinoline. 4-[(Pyridin-3-yl)diazenyl]morpholine (I), C9H12N4O, has monoclinic P21/c symmetry at 100 K, while 1-[(pyridin-3-yl)diazenyl]-1,2,3,4-tetrahydroquinoline (II), C14H14N4, has monoclinic P21/n symmetry at 100 K. These 1,2,3-triazene derivatives were synthesized by the organic medium method by coupling reactions of 3-aminopyridine with morpholine and 1,2,3,4-tetrahydroquinoline, respectively, and characterized by 1H NMR, 13C NMR, IR, mass spectrometry, and single-crystal X-ray diffraction. The molecule of compound I consists of pyridine and morpholine rings connected by an azo moiety (–N=N–). In the molecule of II, the pyridine ring and the 1,2,3,4-tetrahydroquinoline unit are also connected by an azo moiety. The double- and single-bond distances in the triazene chain are comparable for the two compounds. In both crystal structures, the molecules are connected by C—H⋯N interactions, forming infinite chains for I and layers parallel to the bc plane for II.
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