Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Kvyatkovskaya, Elisaveta A., Zaytsev, Vladimir P., Zubkov, Fedor I., Dorovatovskii, Pavel V., Zubavichus, Yan V., Khrustalev, Victor N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
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
_version_ 1782520134893568000
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
work_keys_str_mv AT kvyatkovskayaelisavetaa interactionbetweenmaleicacidandnrfurfurylaminescrystalstructureof2methyln5phenylfuran2ylmethylpropan2aminium2z3carboxyacrylateandn5iodofuran2ylmethyl2methylpropan2aminium2z3carboxyprop2enoate
AT zaytsevvladimirp interactionbetweenmaleicacidandnrfurfurylaminescrystalstructureof2methyln5phenylfuran2ylmethylpropan2aminium2z3carboxyacrylateandn5iodofuran2ylmethyl2methylpropan2aminium2z3carboxyprop2enoate
AT zubkovfedori interactionbetweenmaleicacidandnrfurfurylaminescrystalstructureof2methyln5phenylfuran2ylmethylpropan2aminium2z3carboxyacrylateandn5iodofuran2ylmethyl2methylpropan2aminium2z3carboxyprop2enoate
AT dorovatovskiipavelv interactionbetweenmaleicacidandnrfurfurylaminescrystalstructureof2methyln5phenylfuran2ylmethylpropan2aminium2z3carboxyacrylateandn5iodofuran2ylmethyl2methylpropan2aminium2z3carboxyprop2enoate
AT zubavichusyanv interactionbetweenmaleicacidandnrfurfurylaminescrystalstructureof2methyln5phenylfuran2ylmethylpropan2aminium2z3carboxyacrylateandn5iodofuran2ylmethyl2methylpropan2aminium2z3carboxyprop2enoate
AT khrustalevvictorn interactionbetweenmaleicacidandnrfurfurylaminescrystalstructureof2methyln5phenylfuran2ylmethylpropan2aminium2z3carboxyacrylateandn5iodofuran2ylmethyl2methylpropan2aminium2z3carboxyprop2enoate