The crystal structures of methyl prop-2-ynoate, dimethyl fumarate and their protonated species

Hollenwäger, Dirk ; Bockmair, Valentin und Kornath, Andreas J. (2025): The crystal structures of methyl prop-2-ynoate, dimethyl fumarate and their protonated species. In: Acta Crystallographica Section C Structural Chemistry, Bd. 81, Nr. 1: S. 31-37

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.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 2053-2296
• Sprache: Englisch
• DFG: Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 513247541