Organometallics p. 1369 - 1376 (1986)
Update date:2022-08-05
Topics:
Crociani, Bruno
Sala, Marcellina
Polo, Adriano
Bombieri, Gabriella
Reaction of trans-[PdCl(2-C5H5N)(L)2]Cl (2-C5H5N = N-protonated 2-pyridyl; L = PMe2Ph, PEt3) with an equimolar amount of isocyanide, CNR (R = C6H4OMe-p, Me), followed by deprotonation with NEt3, yields the imino(2-pyridyl)methyl complexes trans-[PdCl{C(2-C5H4N)=NR}(L)2]. These compounds have been characterized by usual spectroscopic techniques and by reaction with ZnCl2, which gives 1:1 binuclear adducts containing the α-diimino group σ,σ′-N,N′ chelated to the zinc center. 1H NMR spectra in CD2Cl2 indicate a predominant E-trans conformation in the temperature range -80-30°C for the imino carbon palladated organic moiety, when not involved in chelation. This is also the only configuration present in the solid state, as shown by an X-ray crystal structure determination of trans-[PdCl{C(2-C5H4N)= NC6H4OMe-p}(PMe2Ph)2]. This compound crystallizes in the monoclinic system: space group P21/n and cell constants a = 16.520 (2) A?, b = 10.953 (1) A?, c = 16.544 (2) A?, β = 97.46 (2)°, and Z = 4. A total of 3969 reflections have been used in the refinement, resulting in a final R value of 0.029. The structure is characterized by a planar N=C-C. .-N α-diimino skeleton, which is perpendicular to the palladium coordination plane (dihedral angle of 86.4 (2)°) and coplanar with the 2-pyridyl ring (dihedral angle of 1.9 (2)°), whereas the phenyl ring of the C6H4OMe-p substituent is rotated by 19.5 (2)°. The coordination around palladium is essentially square-planar, with Pd-C(1) = 2.006 (4), Pd-Cl = 2.430 (2), Pd-P(1) = 2.323 (2), and Pd-P(2) = 2.331 (2) A?.
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Doi:10.1021/ja01176a038
(1949)Doi:10.1021/jo702628g
(2008)Doi:10.1021/ol800141t
(2008)Doi:10.1021/ja01527a042
(1959)Doi:10.1021/jo01095a013
(1958)Doi:10.1016/S0040-4039(00)88929-7
(1985)