Hydrogen Bonding in the Crystal Structures of New Imidazolium Triflimide Protic Ionic Liquids

Bentivoglio, Gino; Schwärzler, Alexander; Wurst, Klaus; Kahlenberg, Volker; Nauer, Gerhard; Bonn, Günther K.; Schottenberger, Herwig; Laus, Gerhard

doi:10.1007/s10870-009-9554-8

Cited by 19 publications

(14 citation statements)

References 34 publications

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“…1. The ions which build this salt, both 1,3-dialkyloxyimidazolium cations (Laus et al, 2010) and the bis(triflimide) anion (Bentivoglio et al, 2009;Laus et al, 2011), are known to exist as syn/anti conformers in the solid state. Thus, the methoxy substituents of the cation adopt an anti conformation with a C5-O1Á Á ÁO2-C6 torsion angle of 170.6 (4) .…”

Section: Structure Descriptionmentioning

confidence: 99%

1,3-Dimethoxy-2-methylimidazolium bis(trifluoromethanesulfonyl)imide

et al. 2016

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, was obtained by the methylation of 1-hydroxy-2-methylimidazole 3-oxide and subsequent ion metathesis. In the crystal, C-HÁ Á ÁO S hydrogen bonds and OÁ Á Á interactions are observed. Structure descriptionThe molecular structure of the title compound is shown in Fig. 1. The ions which build this salt, both 1,3-dialkyloxyimidazolium cations (Laus et al., 2010) and the bis(triflimide) anion (Bentivoglio et al., 2009;Laus et al., 2011), are known to exist as syn/anti conformers in the solid state. Thus, the methoxy substituents of the cation adopt an anti conformation with a C5-O1Á Á ÁO2-C6 torsion angle of 170.6 (4) . The bis(triflimide) anion also assumes an anti conformation with a C7-S1Á Á ÁS2-C8 torsion angle of 174.9 (2) . Each cation donates three C-HÁ Á ÁO S hydrogen bonds to three anions (Fig. 2). The hydrogen-bond parameters are summarized in Table 1. An intriguing intermolecular interaction between atom O3 of the anion and the system of the imidazolium ring is observed. The pertinent O3Á Á ÁCg distance is 2.971 Å , where Cg is the centroid of the heterocyclic ring. This interaction is directional with an S1 O3Á Á ÁCg angle of 152 . The crystal packing is shown in Fig. 3.The cation in the structure of the related 1,3-dimethoxy-2-methylimidazolium tris(-pentafluoroethyl)trifluorophosphate displayed a syn geometry (Laus et al., 2007). AnionÁ Á Á interactions have been observed in related imidazolium salts (Froschauer et al., 2012). The O3Á Á Á interaction and C-HÁ Á ÁO S hydrogen bonds are shown as dashed lines (see Table 1). The centroid of the imidazole ring is drawn as red sphere. Table 1 Hydrogen-bond geometry (Å , ). Figure 3The crystal packing of the title compound viewed along the b axis showing the O3Á Á Á interactions. Figure 1The asymmetric unit of the title compound, showing the atom labels and 50% probability displacement ellipsoids for non-H atoms. of Synthesis and crystallizationA suspension of 1-hydroxy-2-methylimidazole-3-oxide (5.09 g, 44.6 mmol) and dimethyl sulfate (9.0 ml, 100 mmol) in H 2 O (5.0 ml) was stirred at room temperature for 30 min. Calcium carbonate (6.35 g, 63.4 mmol) and H 2 O (6.0 ml) were then added to the slurry, and a slight increase of temperature was observed. The mixture was stirred for 15 h. Then hydrochloric acid (36%; 11.0 ml, 129.2 mmol) was added in portions and stirred for 2 h, resulting in a clear solution. Lithium bis(trifluoromethanesulfonyl)imide (13.0 g, 44.9 mmol) was added, whereupon crystallization of the product occurred. After stirring for 1 h, the mixture was extracted with CH 2 Cl 2 (3 Â 50 ml). The combined organic phases were then washed with H 2 O (100 ml) and dried over Na 2 SO 4 . The solvent was removed under reduced pressure, and the product was dried at 75 C in vacuum (< 1 mbar). On cooling to room temperature the product was obtained as a colourless crystalline solid (yield 97%), mp. 66 C.

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Section: Structure Descriptionmentioning

confidence: 99%

1,3-Dimethoxy-2-methylimidazolium bis(trifluoromethanesulfonyl)imide

et al. 2016

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“…The crystal structures of the precursor 1,3-diaminoimidazolium chloride [4] and the related 1,3-diamino-2-methylimidazolium triflimide [5] have been reported. The geometry of the N-amino groups is pyramidal, indicating sp 3 hybridization.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1,3-diaminoimidazolium hexafluorophosphate, [C3H7N4]PF6

Laus¹,

Kahlenberg²,

Schottenberger³

2010

Zeitschrift Für Kristallographie - New Crystal Structures

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“…The bis(dimethylamino)methane molecule is protonated resulting in a mono-cation. Bis(trifluoromethanesulfonyl)amides [also called 'bis(triflimides)'] are known to exist as either syn or anti conformers in the solid state (Bentivoglio et al, 2009;Laus et al, 2011). Here, the anion adopts an anti conformation with a C6-S1Á Á ÁS2-C7 torsion angle of 169.4 (1) .…”

Section: Structure Descriptionmentioning

confidence: 99%

[(Dimethylamino)methyl]dimethylazanium bis(trifluoromethanesulfonyl)amide

et al. 2016

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The title molecular salt, C5H15N2 +·C2F6NO4S2 −, was obtained by a proton transfer reaction between bis(trifluoromethanesulfonyl)amine and bis(dimethylamino)methane. In the crystal, the ions are linked by N—H...O=S hydrogen bonds, and these units are linked by C—H...O hydrogen bonds, forming sheets parallel to the bc plane. The crystal was refined as a non-merohedral twin with a BASF factor of 0.316 (1).

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Hydrogen Bonding in the Crystal Structures of New Imidazolium Triflimide Protic Ionic Liquids

Cited by 19 publications

References 34 publications

1,3-Dimethoxy-2-methylimidazolium bis(trifluoromethanesulfonyl)imide

1,3-Dimethoxy-2-methylimidazolium bis(trifluoromethanesulfonyl)imide

Crystal structure of 1,3-diaminoimidazolium hexafluorophosphate, [C3H7N4]PF6

[(Dimethylamino)methyl]dimethylazanium bis(trifluoromethanesulfonyl)amide

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