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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, C(15)H(20)NO(+)·C(4)H(3)O(4) (−), (I), and C(9)H(15)INO(+)·C(4)H(3)O(4) (−), (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 r...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5382611/ https://www.ncbi.nlm.nih.gov/pubmed/28435710 http://dx.doi.org/10.1107/S2056989017003541 |
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author | Kvyatkovskaya, Elisaveta A. Zaytsev, Vladimir P. Zubkov, Fedor I. Dorovatovskii, Pavel V. Zubavichus, Yan V. Khrustalev, Victor N. |
author_facet | Kvyatkovskaya, Elisaveta A. Zaytsev, Vladimir P. Zubkov, Fedor I. Dorovatovskii, Pavel V. Zubavichus, Yan V. Khrustalev, Victor N. |
author_sort | Kvyatkovskaya, Elisaveta A. |
collection | PubMed |
description | The title molecular salts, C(15)H(20)NO(+)·C(4)H(3)O(4) (−), (I), and C(9)H(15)INO(+)·C(4)H(3)O(4) (−), (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. |
format | Online Article Text |
id | pubmed-5382611 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-53826112017-04-21 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 Kvyatkovskaya, Elisaveta A. Zaytsev, Vladimir P. Zubkov, Fedor I. Dorovatovskii, Pavel V. Zubavichus, Yan V. Khrustalev, Victor N. Acta Crystallogr E Crystallogr Commun Research Communications The title molecular salts, C(15)H(20)NO(+)·C(4)H(3)O(4) (−), (I), and C(9)H(15)INO(+)·C(4)H(3)O(4) (−), (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. International Union of Crystallography 2017-03-14 /pmc/articles/PMC5382611/ /pubmed/28435710 http://dx.doi.org/10.1107/S2056989017003541 Text en © Kvyatkovskaya et al. 2017 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/ |
spellingShingle | Research Communications Kvyatkovskaya, Elisaveta A. Zaytsev, Vladimir P. Zubkov, Fedor I. Dorovatovskii, Pavel V. Zubavichus, Yan V. Khrustalev, Victor 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 and N-[(5-iodofuran-2-yl)methyl]-2-methylpropan-2-aminium (2Z)-3-carboxyprop-2-enoate |
title | 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 |
title_full | 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 |
title_fullStr | 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 |
title_full_unstemmed | 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 |
title_short | 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 |
title_sort | 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 |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5382611/ https://www.ncbi.nlm.nih.gov/pubmed/28435710 http://dx.doi.org/10.1107/S2056989017003541 |
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