Synthesis and crystal structure of diferrocenylmethoxyethylamine

Abstract

The reaction of diethanolamine with diferrocenylmethyl carbonium (2) that was generated by diferrocenylmethanol (1) treated with BF 3 in CH 2 Cl 2 provided the synthesis of title compound diferrocenylmethoxyethylamine (3). The structure of 3 was determined by the X-ray diffraction (XRD) with crystal data: monoclinic P2 1 /n space group and a = 5.8419 (14) Å, b = 13.572(3) Å, c = 23.839(6) Å, α = 90 • , β = 91.827(5) • , γ = 90 • , V = 1889.2(8) Å 3 , Z = 4, D c = 1.558 mg·m −3 , µ = 1.548 mm −1 , F(000) = 920. The intra-and inter-molecular H bonding modes in 3 were demonstrated both in molecular crystal structure and IR spectral characterization.

1-Ferrocenyl-3-(4-n-octoxylphenyl)propane-1,3-dione

“…The bond angles of adjacent C-C-C in the same cyclopentadienyl ring have a mean value of 108.0°. The data above accord with the literature reported (Glidewell et al, 1996;Zhang et al, 2006). The bond length of C11-C12 (1.398 (3) Å) and C12-C13 (1.387 (2) Å) is shorter than the normal value of single C-C bond (1.54 Å) but close to the normal carboncarbon double bond (1.34 Å) becaused of beta-diketone enolization.…”

“…For related literature, see: Kato (2002); Koizumi et al (2002); Plazuk et al (2001); Zhang et al (2006); Gin et al (2001); Kato et al (2006); Oriol & Serrano (2005); Shi et al (2006); Trzaska et al (1999).…”

Interplay of thermochemistry and Structural Chemistry, the journal (volume 17, 2006) and the discipline

“…The compound crystallizes in a monoclinic P21 space group and according to the structure it was suggested that could serve as catalyst for rocket propellant and as the precursor of chiral ligand or auxiliary for asymmetric syntheses [263]. The next paper by Zhang et al [264] also deals with synthesis of diferrocenyl derivatives. Diferrocenylmethoxyethylamine was synthesized and its structure determined.…”