Nucleophilic substitution of CpFe(CO) 2 (η 2 -H 2 CC(H)OEt) + PF 6with para-substituted anilines was used to prepare a series (4-10) of η 2 -vinyl aniline Fp + complexes of the general formula CpFe(CO) 2 [η 2 -CH 2 C(H)NH(p-C 6 H 4 X)] + PF 6 -, where X ) OMe (4), Me ( 5), H, (6), Br (7), COMe (8), CN (9), and NO 2 (10). Correlation of the Hammett σ para parameters with the 13 C NMR shifts of the metal-coordinated vinyl carbons demonstrated the ability to control the position of the Fp + moiety along the olefin face. As the electron-donating character of the para substituent was increased, the Fp + moiety was displaced away from the nitrogenbearing carbon, increasing the asymmetry of the metal-olefin bonding. These conclusions were further supported by determining the X-ray crystal structure of the p-Me (5) and the p-acetyl (8) derivatives.
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