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Synthesis and Structural Characterization of β-Enaminoester Zinc Complexes

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Abstract

β-Enaminoester zinc complexes were synthesized by reacting ethyl 3-N-(butylimino)-2-butenoate (1) and ethyl 3-N-(hexylimino)-2-butenoate (2), with diethylzinc to afford the desired zinc bis(β-enaminoesterate) complexes 3 and 4. Complex 3, [C24H44N2O4Zn2], crystallized as a dimer in the orthorhombic space group, Pccn with cell parameters: a = 27.1033(7) b = 25.4714(5) c = 8.08614(16) Å, α = β = γ = 90°, V = 5582.3(2) A3, Z = 8. Complex 4, [C28H54N2O4Zn2], crystallizes as a dimer in the triclinic P-1 space group with cell parameters: a = 7.3326(12) Å, b = 8.3623(14) Å, c = 13.887(2) Å, α = 93.839(13)°, β = 91.691(13)°, γ = 112.147(15)°. V = 785.5(2) Å3, Z = 1. The molecular structure of both zinc complexes is comprised of two β-enaminoester zinc ethyl complexes dimerizing through the formation of an out of plane Zn–C bond to an adjoining β-enaminoester zinc ethyl complex moiety.

Graphical Abstract

The reaction of β-enaminoester ligands with an equimolar amount of diethylzinc afforded four coordinate zinc alkyl dimers.

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Acknowledgements

Part of this project was supported by Howard University Graduate School. RJB wishes to acknowledge the NSF-MRI program (Grant CHE-0619278) for funds to purchase the diffractometer as well as the Howard University Nanoscience Facility for access to liquid nitrogen.

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  1. Department of Chemistry, Howard University, Washington, DC, 20059, USA

    Oluwaseun O. Gbemigun, Raymond J. Butcher & Jason S. Matthews

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  1. Oluwaseun O. Gbemigun
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  2. Raymond J. Butcher
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  3. Jason S. Matthews
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Correspondence to Jason S. Matthews.

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Gbemigun, O.O., Butcher, R.J. & Matthews, J.S. Synthesis and Structural Characterization of β-Enaminoester Zinc Complexes. J Chem Crystallogr 49, 80–86 (2019). https://doi.org/10.1007/s10870-018-0736-0

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  • DOI: https://doi.org/10.1007/s10870-018-0736-0

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