Sciact
  • EN
  • RU

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 andN-[(5-iodofuran-2-yl)methyl]-2-methylpropan-2-aminium (2Z)-3-carboxyprop-2-enoate Full article

Journal Acta Crystallographica Section E
, E-ISSN: 2056-9890
Output data Year: 2017, Volume: 73, Number: 4, Pages: 515-519 Pages count : 5 DOI: 10.1107/s2056989017003541
Tags furans; Diels–Alder reaction; maleates; crystal structure; synchrotron radiation
Authors Kvyatkovskaya Elisaveta A. 1 , Zaytsev Vladimir P. 1 , Zubkov Fedor I. 1 , Dorovatovskii Pavel V. 2 , Zubavichus Yan V. 2 , Khrustalev Victor N. 3,4
Affiliations
1 Organic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University)
2 National Research Centre "Kurchatov Institute"
3 Inorganic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University)
4 X-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Abstract: 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 0.072 Å, 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.
Cite: Kvyatkovskaya E.A. , Zaytsev V.P. , Zubkov F.I. , Dorovatovskii P.V. , Zubavichus Y.V. , Khrustalev V.N.
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 andN-[(5-iodofuran-2-yl)methyl]-2-methylpropan-2-aminium (2Z)-3-carboxyprop-2-enoate
Acta Crystallographica Section E. 2017. V.73. N4. P.515-519. DOI: 10.1107/s2056989017003541 WOS Scopus РИНЦ AN OpenAlex
Files: Full text from publisher
Dates:
Submitted: Feb 26, 2017
Accepted: Mar 4, 2017
Published online: Mar 14, 2017
Published print: Apr 1, 2017
Identifiers:
Web of science: WOS:000399190300013
Scopus: 2-s2.0-85017303551
Elibrary: 29501247
Chemical Abstracts: 2017:577480
OpenAlex: W2595426852
Citing:
DB Citing
Web of science 9
Scopus 9
OpenAlex 7
Altmetrics: