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

Oliveira, S. S.; Santin, L. G.; Almeida, L. R.; Malaspina, L. A.; Lariucci, C.; Silva, J. F.; Fernandes, W. B.; Aquino, G. L. B.; Gargano, R.; Camargo, A. J.; Napolitano, H. B. (2017). Synthesis, characterization, and computational study of the supramolecular arrangement of a novel cinnamic acid derivative. Journal of molecular modeling, 23(2) Springer 10.1007/s00894-016-3203-x

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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.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP)

UniBE Contributor:

Malaspina, Lorraine

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry

ISSN:

1610-2940

Publisher:

Springer

Language:

English

Submitter:

Simon Grabowsky

Date Deposited:

18 May 2021 10:31

Last Modified:

18 May 2021 10:31

Publisher DOI:

10.1007/s00894-016-3203-x

BORIS DOI:

10.48350/154629

URI:

https://boris.unibe.ch/id/eprint/154629

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