Interaction between maleic acid and N-R-furfurylamines: Crystal structure of 2-methyl-N-[(5-phenylfuran-2-yl)methyl]propan-2-aminium (2Z)-3-carboxyacrylate and N-[(5-iodofuran-2-yl)methyl]-2-methylpropan-2-aminium (2Z)-3-carboxyprop-2-enoate

The title molecular salts, C15H20NO+·C4H3O4 -, (I), and C9H15INO+·C4H3O4-, (II), have very similar molecular geometries for both cation and anion. The anions of both (I) and (II) are practically planar (r.m.s. deviations = 0.062 and 0.072Å, respectively) and adopt a rare symmetrical geometry with the hydroxy H atom approximately equidistant from the two O atoms. In their crystals, the cations and anions in both (I) and (II) form tight ionic pairs via strong N-H⋯O hydrogen bonds, with a roughly perpendicular disposition of the anion to the furan ring of the cation. This ion-pair conformation appears to correlate with the lack of reactivity of these salts in [4 + 2] cycloaddition reactions. In the extended structures of (I) and (II), the ion pairs form hydrogen-bonded chains propagating along [010] and [001], respectively, via N-H⋯O hydrogen bonds.

Authors
Kvyatkovskaya E.A. 1 , Zaytsev V.P. 1 , Zubkov F.I. 1 , Dorovatovskii P.V.2 , Zubavichus Y.V.2 , Khrustalev V.N. 3, 4
Publisher
International Union of Crystallography
Language
English
Pages
515-519
Status
Published
Volume
73
Year
2017
Organizations
  • 1 Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow, 117198, Russian Federation
  • 2 National Research Centre Kurchatov Institute, 1 Acad. Kurchatov Sq., Moscow, 123182, Russian Federation
  • 3 Inorganic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow, 117198, Russian Federation
  • 4 X-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., B-334, Moscow, 119991, Russian Federation
Keywords
crystal structure; Diels-Alder reaction; furans; maleates; synchrotron radiation
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