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On the nature of the interaction of copper hydride and halide with substituted ethylene and acetylene

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Abstract

The association of Cu–X (X = –H, –Cl, and –F) with H2CCHCHmYn and HCCCHmYn (Y = –Cl, –F, –OH, –CH3) has been studied at a high level of theory. The density functional theory (DFT) at B3LYP/6-311G(d,p)//B3LYP/6-311 + G(3df,2p) level has been chosen to calculate the structure and the relative stability of 24 different complexes. The interaction of Cu–F with the derivatives of ethylene and acetylene was found very strong, with interaction energies close to those of conventional covalent bonds. In all complexes, the most stable structure was found when Cu–X is positioned on the unsaturated CC bond, forming a three-membered ring that leads to longer CC bond distances. Both ethylene and acetylene complexes show similar trends of interaction energies with respect to the same moiety. All electronic indexes analyzed by means of the QTAIM, ELF, and NBO formalisms indicate that the strength of the interaction should increase with the number of withdrawing substituents in both series of compounds.

The p-Interaction of ethylene and acetylene derivative with fluoride copper. The ELF graphs and its 2D projection show the disynaptic basins of the electrostatic binding

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Acknowledgments

This work has been partially supported by the FONDECYT REGULAR 1170837 (BH) DGI Projects no. CTQ2015-63997-C2. A generous allocation of computing time at the Centro de Computación Científica of the UAM is also acknowledged (AML).

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Authors and Affiliations

  1. Departamento de Química, C-9, Universidad Autónoma de Madrid. Campus de Excelencia UAM-CSIC Cantoblanco, 28049, Madrid, Spain

    Serra Arslancan & Al Mokhtar Lamsabhi

  2. QTC, Pontificia Universidad Católica de Chile, Av. Vicuña Mackenna 4860, Macul, Santiago, Chile

    Barbara Herrera

  3. Institute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, 28049, Madrid, Spain

    Al Mokhtar Lamsabhi

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  1. Serra Arslancan
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  2. Barbara Herrera
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Correspondence to Al Mokhtar Lamsabhi.

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Arslancan, S., Herrera, B. & Lamsabhi, A.M. On the nature of the interaction of copper hydride and halide with substituted ethylene and acetylene. J Mol Model 26, 61 (2020). https://doi.org/10.1007/s00894-020-4320-0

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