Abstract
Substituted triazines are a class of compounds utilized for scavenging and sequestering hydrogen sulfide in oil and gas production operations. The reaction of one of these triazines under field conditions resulted in the formation of the title compound, 2-(1,3,5-di-thia-zinan-5-yl)ethanol, C5H11NOS2, or MEA-di-thia-zine. Polymorphic form I, in space group I41/a, was first reported in 2004 and its extended structure displays one-dimensional, helical strands connected through O-H⋯O hydrogen bonds. We describe here the form II polymorph of the title compound, which crystallizes in the ortho-rhom-bic space group Pbca as centrosymmetric dimers through pairwise O-H⋯N hydrogen bonds from the hydroxyl moiety to the nitro-gen atom of an adjacent mol-ecule.
Highlights
Substituted triazines are a class of compounds utilized for scavenging and sequestering hydrogen sulfide in oil and gas production operations
The reaction of one of these triazines under field conditions resulted in the formation of the title compound, 2-(1,3,5-dithiazinan-5-yl)ethanol, C5H11NOS2, or MEA-dithiazine
We describe here the form II polymorph of the title compound, which crystallizes in the orthorhombic space group Pbca as centrosymmetric dimers through pairwise O—HÁ Á ÁN hydrogen bonds from the hydroxyl moiety to the nitrogen atom of an adjacent molecule
Summary
Hydrogen sulfide is a corrosive and lethal gas that is commonly encountered during the production of hydrocarbons from subterranean reservoirs (Marriott et al, 2016). The title compound has this in common with the other structures featuring a MEA-dithiazine moiety: The previously reported polymorph (form I) in space group I41/a and the bromide and chloride salts of MEA-dithiazine, which are protonated at the amine and isomorphous (Bushmarinov et al, 2009; Galvez-Ruiz et al, 2008), feature an sp3-hybridized amine N atom, as well as a chair conformation dithiazine ring axially substituted by the ethanolamine. The form I polymorph and the salts exhibit the same chair conformation and axial position of the ethanolamine group as well as a common gauche conformation of the ethanolamine chain as observed for form II of the title compound, indicating a clear preference of the MEA-dithiazine molecule towards this specific molecular conformation. The cause for the differences between the two polymorphs and the salt can be found among the intermolecular and packing interactions, to be discussed below
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