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Two Bifunctionalised Derivatives of 1,2,4-Triazole

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Abstract

Structures are described for the aldehyde 3,5-bis[2-(2′-formylphenoxymethyl)]-1,2,4-triazole and the new pyrazole compound 3,5-bis[(3′,5′-dimethyl)methylpyrazol-1′N-yl)]-1,2,4-triazole, for which the synthesis is given. The former crystallises in the space group Pna21 and the latter in P1[bar]. The remaining triazole N–H moiety forms hydrogen bonds, and is not disordered in the solid state. This latter property and molecular twisting features associated with the molecules' individually chiral conformations are commented upon. The electronic spectra are reported, with DFT calculations indicating that the much longer-wavelength UV absorptions of the aldehyde are dominated by the benzaldehyde moieties.

Graphical Abstract

A dialdehyde and a bis(pyrazole) derivative of 1,2,4-triazole are elucidated. The pyrazole derivative displays triazole-based H-bonding in the solid state which links molecules of individually opposite chirality into centrosymmetric dimers.

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Acknowledgements

JPJ acknowledges the NSF-MRI program (Grant No.CHE-1039027) for funding of the Gemini X-ray diffractometer. We thank Drexel University (SE and AWA) and Stockton University (GTR) for support.

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Author notes

  1. Jerry P. Jasinski—Deceased.

Authors and Affiliations

  1. Department of Chemistry, Drexel University, 3141 Chestnut St., Philadelphia, PA, 19104-2816, USA

    Sadik Elshani & Anthony W. Addison

  2. Polysciences, Inc., 400 Valley Road, Warrington, PA, 18976, USA

    Sadik Elshani

  3. Department of Chemistry, Keene State College, Keene, NH, 03435, USA

    Jerry P. Jasinski

  4. Chemistry Program, School of Natural Sciences and Mathematics, Stockton University, Galloway, NJ, 08205, USA

    GorDan T. Reeves

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  1. Sadik Elshani
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  2. Jerry P. Jasinski
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  4. GorDan T. Reeves
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Correspondence to Anthony W. Addison.

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Elshani, S., Jasinski, J.P., Addison, A.W. et al. Two Bifunctionalised Derivatives of 1,2,4-Triazole. J Chem Crystallogr 52, 458–468 (2022). https://doi.org/10.1007/s10870-021-00916-y

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  • DOI: https://doi.org/10.1007/s10870-021-00916-y

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