engleski

Structure of heteroannularly disubstituted ferrocene derivatives containing acetamido group

Methyl 1 -(acetamido)ferrocene-1-carboxylate (2), 1’ -acetamidoferrocene-1-carboxazide (4) and methyl 1'-(1-acetamidoethyl)ferrocene-1-carboxylate (6) have been prepared and fully characterized. X-ray single crystal analysis showed that acetamido group in 2 and 4, methoxycarbonyl group in 2 and 6 and azidocarbonyl group in 4 are coplanar with adjacent cyclopentadienyl rings. In compound 6 acetamido group is perpendicular with respect to the plane of the cyclopentadienyl ring. In 2 and 6 ferrocene cyclopentadienyl rings adopt eclipsed conformation, while in 4 they deviate only slightly from this conformation. The molecules of 2 and 6 are self-assembled by one N– H   O intermolecular hydrogen bond into infinite chains, while N– H   O hydrogen bond in derivative 4 forms centrosymmetric dimer. 1H NMR and IR spectra measured in diluted solutions showed that acetamido-ester 2 existed in a free form, and 6 contained intramolecular hydrogen-bonded conformer accompanied with a small quantity of the open form. Furthermore, the molecules of acetamido-azide 4 were nonhydrogen-bonded under the same conditions, and in concentrated solutions they are self-assembled.

bioorganometallic chemistry; ferrocene derivatives; hdrogen bonds; X-ray single crystal analysis; spectroscopic analysis

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