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Inter ­ action between maleic acid and N - R -furfuryl ­ amines: crystal structure of 2-methyl- N -[(5-phenyl ­ furan-2-yl)meth ­ yl]propan-2-aminium (2 Z )-3-carb ­ oxy ­ acrylate and N -[(5-iodo ­ furan-2-yl)meth ­ yl]-2-methyl ­ propan-2-aminium (2 Z )-3-carb ­ oxy ­ prop-2-enoate

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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.

No MeSH data available.


The crystal structure of (I), illustrating the hydrogen-bonded chains propagating along [010]. Dashed lines indicate the intra­molecular O—H⋯O and inter­molecular N—H⋯O hydrogen bonds.
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fig5: The crystal structure of (I), illustrating the hydrogen-bonded chains propagating along [010]. Dashed lines indicate the intra­molecular O—H⋯O and inter­molecular N—H⋯O hydrogen bonds.

Mentions: Despite the sterically different substituents at the furyl ring of the aminium cations, compounds (I) and (II) organize similar supra­molecular structures in the solid state. So, in the crystal of (I), the tight ion pairs form hydrogen-bonded chains propagating along [010] via strong N1—H1B⋯O4 links (Table 1 ▸, Fig. 5 ▸). In the crystal of (II), the analogous hydrogen-bonded chains propagate along [001] (Table 2 ▸, Fig. 6 ▸). In both (I) and (II), the chains are further packed in stacks along [100] (Figs. 5 ▸ and 6 ▸).


Inter ­ action between maleic acid and N - R -furfuryl ­ amines: crystal structure of 2-methyl- N -[(5-phenyl ­ furan-2-yl)meth ­ yl]propan-2-aminium (2 Z )-3-carb ­ oxy ­ acrylate and N -[(5-iodo ­ furan-2-yl)meth ­ yl]-2-methyl ­ propan-2-aminium (2 Z )-3-carb ­ oxy ­ prop-2-enoate
The crystal structure of (I), illustrating the hydrogen-bonded chains propagating along [010]. Dashed lines indicate the intra­molecular O—H⋯O and inter­molecular N—H⋯O hydrogen bonds.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5382611&req=5

fig5: The crystal structure of (I), illustrating the hydrogen-bonded chains propagating along [010]. Dashed lines indicate the intra­molecular O—H⋯O and inter­molecular N—H⋯O hydrogen bonds.
Mentions: Despite the sterically different substituents at the furyl ring of the aminium cations, compounds (I) and (II) organize similar supra­molecular structures in the solid state. So, in the crystal of (I), the tight ion pairs form hydrogen-bonded chains propagating along [010] via strong N1—H1B⋯O4 links (Table 1 ▸, Fig. 5 ▸). In the crystal of (II), the analogous hydrogen-bonded chains propagate along [001] (Table 2 ▸, Fig. 6 ▸). In both (I) and (II), the chains are further packed in stacks along [100] (Figs. 5 ▸ and 6 ▸).

View Article: PubMed Central - HTML - PubMed

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.

No MeSH data available.