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Volume 15
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10.3390/cryst15090750
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Article

X-Ray Structures of Some Heterocyclic Sulfones

by
R. Alan Aitken
*,
David B. Cordes
,
Aidan P. McKay
,
Alexandra M. Z. Slawin
and
Dheirya K. Sonecha
EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK
*
Author to whom correspondence should be addressed.
Crystals 2025, 15(9), 750; https://doi.org/10.3390/cryst15090750
Submission received: 7 August 2025 / Revised: 21 August 2025 / Accepted: 22 August 2025 / Published: 24 August 2025
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Abstract

1,4-Thiazine S,S-dioxide 1, the cis- and trans-isomers 2 and 3 of its precursor 2,6-diethoxy-1,4-oxathiane S,S-dioxide, and diethyl 2,3-dihydro-1,4-thiazine-3,5-dicarboxylate S,S-dioxide 4 have been fully characterised, both in solution by 1H and 13C NMR and in the solid state by X-ray diffraction. Simulation has been used to model the unexpectedly complex 1H NMR spectra and arrive at a full assignment of all chemical shifts and coupling constants. The crystal structures of both 1 and 4, which adopt, respectively, boat and half-chair conformations, are dominated by strong NH to O=S hydrogen bonding leading to chains of molecules. In the case of 4, the NMR data point to an equatorial position of the C(2)-ester group in solution, while in the crystal, this adopts an axial orientation. Compounds 2 and 3 adopt chair conformations both in solution and in the solid state with ring inversion on the NMR timescale leading to unexpected simplification of the spectra in the case of 3.
Keywords: 1,4-thiazine S,S-dioxide; 1,4-oxathiane S,S-dioxide; NMR assignment; hydrogen bonding 1,4-thiazine S,S-dioxide; 1,4-oxathiane S,S-dioxide; NMR assignment; hydrogen bonding

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MDPI and ACS Style

Aitken, R.A.; Cordes, D.B.; McKay, A.P.; Slawin, A.M.Z.; Sonecha, D.K. X-Ray Structures of Some Heterocyclic Sulfones. Crystals 2025, 15, 750. https://doi.org/10.3390/cryst15090750

AMA Style

Aitken RA, Cordes DB, McKay AP, Slawin AMZ, Sonecha DK. X-Ray Structures of Some Heterocyclic Sulfones. Crystals. 2025; 15(9):750. https://doi.org/10.3390/cryst15090750

Chicago/Turabian Style

Aitken, R. Alan, David B. Cordes, Aidan P. McKay, Alexandra M. Z. Slawin, and Dheirya K. Sonecha. 2025. "X-Ray Structures of Some Heterocyclic Sulfones" Crystals 15, no. 9: 750. https://doi.org/10.3390/cryst15090750

APA Style

Aitken, R. A., Cordes, D. B., McKay, A. P., Slawin, A. M. Z., & Sonecha, D. K. (2025). X-Ray Structures of Some Heterocyclic Sulfones. Crystals, 15(9), 750. https://doi.org/10.3390/cryst15090750

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