SYNTHESIS AND CHARACTERIZATION OF THE NEW DIAZA FERROCENE MACROCYCLE 1,1'-(2,6-DIAZAHEPTA-1,6-DIENE)FERROCENE AND ITS PARENT AMINE 1,1'-(2,6-DIAZAHEPTANE)FERROCENE
Mjl. Tendero et al., SYNTHESIS AND CHARACTERIZATION OF THE NEW DIAZA FERROCENE MACROCYCLE 1,1'-(2,6-DIAZAHEPTA-1,6-DIENE)FERROCENE AND ITS PARENT AMINE 1,1'-(2,6-DIAZAHEPTANE)FERROCENE, Inorganica Chimica Acta, 247(1), 1997, pp. 139-142
Reaction of ferrocene-1,1'-dicarbaldehyde and propylenediamine yields
the Schiff-base derivative 1,1'-(2,6-diazahepta-1,6-diene)ferrocene (1
), The molecular structure of 1 has been determined by single crystal
X-ray analysis. It crystallises in the monoclinic system, space group
P2(1)/c, a=13.507(3), b=9.800(2), c=10.086(2) Angstrom, beta=110.81(3)
degrees, Z=4 and V=1248.0(5) Angstrom(3). Refinement of the atomic par
ameters by least-squares techniques gave a final R factor of 0.074 for
1588 observed reflections having I> 2 sigma(I). Hydrogenation of 1 wi
th LiAlH4 results in the parent amine 1,1'-(2,6-diazaheptane)ferrocene
(2). The protonation of 2 has been investigated by potentiometry in w
ater in the pH range 11-6. At pH lower than 6, 2 is unstable in soluti
on. The E-1/2 potential for 2 is pH-dependent (E-1/2(pH 11)=255, E-1/2
(pH 6)=435 mV). A similar behaviour was also observed in THF:water (60
:40 vol./vol.). The electrochemical behaviour for 1 and 2 has also bee
n studied in CH2Cl2.