W. Smith, J. Ekstrand, K. Raymond
May 24, 1978
Citations
0
Influential Citations
31
Citations
Journal
Journal of the American Chemical Society
Abstract
The title compound, 1,5,9,13-tetraazacyclohexadecane (I), has been prepared in 60% yield on both a 0.01- and a 0.2-mol scale by the condensation of the ditosylate of 1,3-propanediol with the disodium salt of N,N',N'',N'''-tetra-p-toluene-sulfonyl-N,N'-bis(3-aminopropyl)-1,3-propanediamine, followed by the removal of the tosylate groups in 98% sulfuric acid. The crystal structure of I was determined from x-ray diffraction data collected by countermethods. The overall symmetry of the molecule, excluding the nitrogen hydrogen atoms is D/sub 2d/. That the amine hydrogens on adjacent nitrogens are trans lowers the molecular symmetry to S/sub 4/, which is obeyed within experimental error. The four nitrogens form a square with an average edge length of 2.925 (4) A. The trimethylene groups are in chair configurations with adjacent groups folding toward opposite sides of the nitrogen plane. Refinement on F/sup 2/ using all 1866 measured independent reflections by full-matrix least-squares led to an R factor of 6.6%. Unit cell dimensions in the space group P2/sub 1//n are a = 12.764 (6), b = 12.201 (6), c = 9.579 (4) A; ..beta.. = 108.13 (3)/sup 0/; and the calculated density is 1.07 g cm/sup -3/ for z = 4. 3 tables, 4 figures, 64 references.