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Kinetics of Nucleophilic Attack on Co-ordinated Organic Moieties. PART 15. Addition of p-Toluidine to Tricarbonyl(1-5-η-dienyl)iron Cations

DOI: 10.1039/DT9810000200

Source and publish data:

Journal of the Chemical Society, Dalton Transactions p. 200 - 204 (1981)

Update date:2022-07-30

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Authors:

Kane-Maguire, Leon A. P.Kane-Maguire, Leon A. P.

Odiaka, Tim I.Odiaka, Tim I.

Williams, Peter A.Williams, Peter A.

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Article abstract of DOI:10.1039/DT9810000200

The reactions of the cations 5-dienyl)(CO)3>+ (1; dienyl = C6H7, C6H6OMe-2, or C7H9) with p-toluidine in CH3CN have been shown to give the neutral adducts 4-diene.NHC6H4CH3)(CO)3> (2) according to the equation (1) + 2CH3C6H4NH2 --> (2) + +.The products have been characterised by analyses, 1H n.m.r., i.r., and field-desorption mass spectroscopy.The reactions could be reversed by the addition of acid.A stopped-flow kinetic study of the above reactions in CH3CN yields the general rate law, Rate = k.These results are rationalised in terms of two-step mechanism involving initial reversible addition (k1, k-1) of p-toluidine to the dienyl rings to form the cationic intermediates 4-diene*NH2C6H4CH3)>+ (3), followed by rapid proton loss, k2 (either solvent- or amine-assisted).For such a mechanism the kobs. values refer to k1, which is consistent with the observed order of reactivity of the cations at 0 deg C (C6H7 > C6H6OMe-2 > C7H9, 17 : 2.6 :1), and the low ΔHI and negative ΔSI values.

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