X-ray powder diffraction, solid-state NMR and dispersion-corrected DFT calculations to investigate the solid state structure of 2-ammonio-5-chloro-4-methylbenzenesulfonate
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Sandor L. Bekö
Abstract
The title compound, also called CLT acid, is an industrial intermediate in the synthesis of laked red azo pigments for newspaper printing. Solid-state NMR and IR experiments revealed the compound to exist as the zwitterionic tautomer in the solid state.
The crystal structure was solved from X-ray powder diffraction data by means of real-space methods using the program DASH 3.1. Subsequently the structure was refined by the Rietveld method with TOPAS 4.1. The zwitterionic tautomer gave better confidence values than the non-zwitterionic tautomer. Finally the structure was confirmed by dispersion-corrected density-functional calculations.
The compound crystallises in the monoclinic space group Ia, Z = 4 with a = 5.49809(7) Å, b = 32.8051(5) Å, c = 4.92423(7) Å, β = 93.5011(7)° and V = 886.50(2) Å3. The molecules form a herringbone pattern with a double layer structure consisting of alternating polar and non-polar layers. Within the polar layers hydrogen bonds and ionic interactions are dominant, whereas the fragments in the non-polar layers are connected by van der Waals interactions.
© by Oldenbourg Wissenschaftsverlag, Frankfurt am Main, Germany
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Articles in the same Issue
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- The phase transition to the low-temperature form of (D5O2)[SbCl6] and determination of the deuterium positions
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- Mixed salts of amino acids: Syntheses, crystal structure and vibrational spectra of L-histidinium(2+) · NO3 · ClO4 and L-histidinium(2+) · NO3 · BF4
- Synthesis, X-ray analysis and DFT study of 2-amino-3-(N-oxipiridin-4-ilsulfanil)-propionic acid dihydrate
- Discussion of unusual hydrogen atom display in solid acids
