STUDIES OF THE SYNTHESIS, PROTONATION AND DECOMPOSITION OF 2,4,6,8,10,12-HEXABENZYL-2,4,6,8,10,12-HEXAAZATETRACYCLO[5.5.0.0(5,9).0(3,11)]DODECANE (HBIW)

• Published in: Journal of the Chemical Society, Perkin Transactions 2 no. 5; pp. 923 - 929
• Main Authors: CRAMPTON, MR, HAMID, J, MILLAR, R, FERGUSON, G
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 1993; Royal Society of Chemistry
• Subjects: Chemistry; Chemistry, Organic; Chemistry, Physical; Condensed matter: structure, mechanical and thermal properties; Exact sciences and technology; Heterocyclic compounds; Kinetics and mechanisms; Organic chemistry; Organic compounds; Physical Sciences; Physics; Reactivity and mechanisms; Science & Technology; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; PRIMARY AMINES; GLYOXAL DERIVATIVES; Cage compound; Molecular structure; Nitrogen heterocycle; Dialdehyde; Polycyclic compound; Glyoxal; Experimental study; X ray diffraction; Acetonitrile; Chemical decomposition; Protonation; Aqueous solution; Rate constant; Primary amine; Organic compounds; Crystalline structure
• ISSN: 0300-9580; 2050-8239; 1364-5471
• DOI: 10.1039/p29930000923

Reaction of glyoxal with benzylamine or with substituted benzylamines leads to the cage structure 3. The X-ray crystal structure of 3c formed from 4-chlorobenzylamine is reported. H-1 and C-13 NMR spectra of 3a-j have been measured. Changes in spectra in the presence of acid indicate successive reaction to give mono- and di-protonated species, 4 and 5 respectively, in which the added protons bridge two nitrogen atoms. The kinetics of the decomposition of 3a in aqueous acetonitrile are compatible with two competing pathways involving reaction of the protonated form with either water or more acid.