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Abstract
Methyl prop-2-ynoate (C4H4O2) was investigated in the binary superacidic system HF/MF5 (M = Sb or As) and dimethyl fumarate (C6H8O4) in the superacidic system HF/SbF5, as well as HF/BF3. The starting materials methyl prop-2-ynoate and dimethyl fumarate were crystallized, the former for the first time. The protonated species of these esters, namely, (1-methoxyprop-2-yn-1-ylidene)oxidanium hexafluoroarsenate, C4H5O2+ AsF6-, 1,4-dimethoxy-4-oxobut-2-en-1-ylidene]oxidanium tetrafluoroborate bis(hydrogen fluoride), C6H9O4+ BF4- 2HF, and hemi{[1,4-dimethoxy-4-oxidaniumylidenebut-2-en-1-ylidene]oxidanium} undecafluorodiantimonate, 0.5C6H10O42+ Sb2F11-, were characterized by single-crystal X-ray diffraction and Raman spectroscopy. The protonated species were recrystallized from anhydrous hydrogen fluoride. In the solid state of the monoprotonated species of methyl prop-2-ynoate and the diprotonated species of dimethyl fumarate, strong intramolecular O-H...F hydrogen bonds build a three-dimensional network. The monoprotonated species of dimethyl fumarate builds chains by strong O-H...O hydrogen bonds between the cations.
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Schedule a callMore From: Acta crystallographica. Section C, Structural chemistry
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