European Journal of Chemistry 2018, 9(3), 151-160 | doi: https://doi.org/10.5155/eurjchem.9.3.151-160.1734 | Get rights and content






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Structural study of three heteroaryl oximes, heteroaryl-N=OH: Compounds forming strong C3 molecular chains


John Nicolson Low (1) orcid , James Lewis Wardell (2) orcid , Cristiane Franca da Costa (3) orcid , Marcus Vicinius Nora Souza (4) orcid , Ligia Rebelo Gomes (5,*) orcid

(1) Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland
(2) Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland
(3) Instituto de Tecnologia em Fármacos e Farmanguinhos, Fundação Oswaldo Cruz, 21041-250 Rio de Janeiro, Rio de Janeiro, Brazil
(4) Instituto de Tecnologia em Fármacos e Farmanguinhos, Fundação Oswaldo Cruz, 21041-250 Rio de Janeiro, Rio de Janeiro, Brazil
(5) FP-ENAS-Faculdade de Ciências de Saúde, Escola Superior de Saúde da UFP, Universidade Fernando Pessoa, Rua Carlos da Maia, 296, P-4200-150 Porto, Portugal
(*) Corresponding Author

Received: 14 May 2018 | Revised: 04 Jun 2018 | Accepted: 05 Jun 2018 | Published: 30 Sep 2018 | Issue Date: September 2018

Abstract


In order to further investigate the structural chemistry of oximes and to further establish the main structural arrangements adopted, we have determined the crystal structure of and carried out Hirshfeld surface calculations on three heteroaryl oximes, namely (Z)-thiophene-2-carbaldehyde oxime (1), (Z)-1H-pyrrole-2 carbaldehyde oxime (2) and (Z)-5-nitrofuran-2-carbaldehyde oxime (3). As confirmed by both techniques, the major intermolecular interactions in each compound are classical N—H···O hydrogen bonds, which link the molecules into C3 chains. Such an arrangement has been previous reported as an important aggregation mode for oximes. Secondary interactions, C—H···π and C—H···O interactions, in compounds 1 and 2, and interactions involving the nitro group oxygen atoms in compound 3 link the chains into three dimensional arrays.


Keywords


Oximes; Hydrogen bonds; X-ray crystallography; Molecular interactions; Heteroaryl compounds; Hirshfeld surface calculations

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DOI: 10.5155/eurjchem.9.3.151-160.1734

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Funding information


Portuguese Foundation for Science and Technology (FCT) UID/Multi/04546/2013

Citations

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[1]. Ligia R. Gomes, John N. Low, Tanja van Mourik, Herbert Früchtl, Marcus V.N. de Souza, Cristiane F. da Costa, James L. Wardell
Different substituent effects on the supramolecular arrays in some (E)-halo- and nitro-benzaldehyde oximes: confirmation of attractive π(C=N)···π(phenyl) interactions
Zeitschrift für Naturforschung B  74(4), 319, 2019
DOI: 10.1515/znb-2018-0222
/


[2]. Ligia R. Gomes, Marcus V. N. de Souza, Cristiane F. Da Costa, James L. Wardell, John Nicolson Low
Crystal structures and Hirshfeld surfaces of four methoxybenzaldehyde oxime derivatives, 2-MeO-XC6H3C=NOH (X = H and 2-, 3- and 4-MeO): different conformations and hydrogen-bonding patterns
Acta Crystallographica Section E Crystallographic Communications  74(11), 1553, 2018
DOI: 10.1107/S2056989018014020
/


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Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Low, J.; Wardell, J.; da Costa, C.; Souza, M.; Gomes, L. Eur. J. Chem. 2018, 9(3), 151-160. doi:10.5155/eurjchem.9.3.151-160.1734
Low, J.; Wardell, J.; da Costa, C.; Souza, M.; Gomes, L. Structural study of three heteroaryl oximes, heteroaryl-N=OH: Compounds forming strong C3 molecular chains. Eur. J. Chem. 2018, 9(3), 151-160. doi:10.5155/eurjchem.9.3.151-160.1734
Low, J., Wardell, J., da Costa, C., Souza, M., & Gomes, L. (2018). Structural study of three heteroaryl oximes, heteroaryl-N=OH: Compounds forming strong C3 molecular chains. European Journal of Chemistry, 9(3), 151-160. doi:10.5155/eurjchem.9.3.151-160.1734
Low, John, James Lewis Wardell, Cristiane Franca da Costa, Marcus Vicinius Nora Souza, & Ligia Rebelo Gomes. "Structural study of three heteroaryl oximes, heteroaryl-N=OH: Compounds forming strong C3 molecular chains." European Journal of Chemistry [Online], 9.3 (2018): 151-160. Web. 5 Dec. 2020
Low, John, Wardell, James, da Costa, Cristiane, Souza, Marcus, AND Gomes, Ligia. "Structural study of three heteroaryl oximes, heteroaryl-N=OH: Compounds forming strong C3 molecular chains" European Journal of Chemistry [Online], Volume 9 Number 3 (30 September 2018)

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DOI Link: https://doi.org/10.5155/eurjchem.9.3.151-160.1734

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