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Synthesis, characterization, and computational study of the supramolecular arrangement of a novel cinnamic acid derivative

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Abstract

In this work, we present the synthesis, characterization, and computational study of the supramolecular arrangement of a new cinnamic acid derivative: ethyl-(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-prop-2-enoate (EHD). Single crystals of EHD were obtained using ethyl ether as solvent and a slow evaporation technique. Its crystallographic structure, derived from X-ray diffraction experiments, includes a disordered water molecule on the EHD supramolecular structure. This water molecule participates in four O–H···O hydrogen bonds, which are arranged as a centrosymmetric H-bond array with the water at the center. Electronic and structural properties of the isolated EHD molecule and of the EHD molecule in the presence of one water molecule were calculated at the B3LYP/6-311++G(2d,2p) level of theory. These calculations show that the HOMO–LUMO energy gap of EHD decreases upon the introduction of the water molecule, suggesting that EHD becomes a stronger electron acceptor. These results indicate that the water molecule helps to stabilize the crystal structure in this system containing unequal numbers of acceptor and donor atoms. The supramolecular synthon involving the disordered water molecule and the supramolecular features presented here provide new possibilities in the design of functional materials and should also help us to gain a deeper understanding of the processes by which molecules recognize biological targets.

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Acknowledgements

The authors gratefully acknowledge the financial support of the National Council of Technological and Scientific Development (CNPq), Brazil. The authors are also grateful to Prof. Robert Burrow at the Chemistry Department of the Federal University of Santa Maria (UFSM) for data collection and fruitful discussions.

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Authors and Affiliations

  1. Campus de Ciências Exatas e Tecnológicas, Universidade Estadual de Goiás, PO Box 459, 75001-970, Anápolis, GO, Brazil

    S. S. Oliveira, L. R. Almeida, J. F. Silva, W. B. Fernandes, G. L. B. Aquino, A. J. Camargo & H. B. Napolitano

  2. Instituto de Física, Universidade de Brasília, PO Box. 04455, 70904-970, Brasília, Brazil

    L. G. Santin & R. Gargano

  3. Instituto de Física, Universidade Federal de Goiás, Campus Samambaia, PO Box 131, 74001-970, Goiânia, GO, Brazil

    L. A. Malaspina & C. Lariucci

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  1. S. S. Oliveira
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  2. L. G. Santin
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  3. L. R. Almeida
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  4. L. A. Malaspina
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  5. C. Lariucci
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  6. J. F. Silva
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  7. W. B. Fernandes
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  8. G. L. B. Aquino
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  9. R. Gargano
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  10. A. J. Camargo
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  11. H. B. Napolitano
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Correspondence to H. B. Napolitano.

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This paper belongs to Topical Collection Brazilian Symposium of Theoretical Chemistry (SBQT2015)

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Oliveira, S.S., Santin, L.G., Almeida, L.R. et al. Synthesis, characterization, and computational study of the supramolecular arrangement of a novel cinnamic acid derivative. J Mol Model 23, 35 (2017). https://doi.org/10.1007/s00894-016-3203-x

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