ArticleActa crystallographica. Section C, Structural chemistry2014
Distinguishing tautomerism in the crystal structure of (Z)-N-(5-ethyl-2,3-dihydro-1,3,4-thiadiazol-2-ylidene)-4-methylbenzenesulfonamide using DFT-D calculations and (13)C solid-state NMR.
Article in Acta crystallographica. Section C, Structural chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed.
- An NMR crystallography investigation of furosemide.Magnetic resonance in chemistry : MRC · 2019Article
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- Getting the chemistry right: protonation, tautomers and the importance of H atoms in biological chemistry.Acta crystallographica. Section D, Structural biology · 2017Article
- Rationalization of the Color Properties of Fluorescein in the Solid State: A Combined Computational and Experimental Study.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Navigating the Waters of Unconventional Crystalline Hydrates.Molecular pharmaceutics · 2015Article
- Validation of molecular crystal structures from powder diffraction data with dispersion-corrected density functional theory (DFT-D).Acta crystallographica Section B, Structural science, crystal engineering and materials · 2014Article
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4 authors.
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Abstract
The crystal structure of the title compound, C11H13N3O2S2, has been determined previously on the basis of refinement against laboratory powder X-ray diffraction (PXRD) data, supported by comparison of measured and calculated (13)C solid-state NMR spectra [Hangan et al. (2010). Acta Cryst. B66, 615-621]. The molecule is tautomeric, and was reported as an amine tautomer [systematic name: N-(5-ethyl-1,3,4-thiadiazol-2-yl)-p-toluenesulfonamide], rather than the correct imine tautomer. The protonation site on the molecule's 1,3,4-thiadiazole ring is indicated by the intermolecular contacts in the crystal structure: N-H...O hydrogen bonds are established at the correct site, while the alternative protonation site does not establish any notable intermolecular interactions. The two tautomers provide essentially identical Rietveld fits to laboratory PXRD data, and therefore they cannot be directly distinguished in this way. However, the correct tautomer can be distinguished from the incorrect one by previously reported quantitative criteria based on the extent of structural distortion on optimization of the crystal structure using dispersion-corrected density functional theory (DFT-D) calculations. Calculation of the (13)C SS-NMR spectrum based on the correct imine tautomer also provides considerably better agreement with the measured (13)C SS-NMR spectrum.
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