Letter: Evidence for the clustering of substituted imidazolium salts via hydrogen bonding under the conditions of fast atom bombardment mass spectrometry

Abdul‐Sada, Alaa; Elaiwi, Ahmed E.; Greenway, Anthony M.; Seddon, Kenneth R.

doi:10.1255/ejms.18

Cited by 47 publications

(43 citation statements)

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“…and x > n), respectively, [35] whereas in fast atom bombardment mass spectroscopy (FAB-MS) clusters of the type [(CA)C] + were present. [36] These findings, together with our results on the appearance of cluster ions, underline the previously calculated organisation of ionic liquids in the condensed phase. The energy deposition on the surface in ToF-SIMS experiments is very high, and hydrogen-bonded long chain molecules are easily cleaved to smaller oligomers.…”

Section: Mass Spectra -Fragmentation Patternsupporting

confidence: 88%

Investigation of ionic liquids under Bi‐ion and Bi‐cluster ions bombardment by ToF‐SIMS

2010

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A systematic study of five different imidazolium-based room temperature ionic liquids, 1-butyl-3-methylimidazolium acetate, 1-butyl-3-methylimidazolium nitrate, 1-butyl-3-methylimidazolium iodide, 1-butyl-3-methylimidazolium hexafluorophosphate and 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide were carried out by means of time-of-flight secondary ion mass spectrometry (ToF-SIMS) in positive and negative ion mode. The compounds were measured under Bi-ion and Bi-cluster ions (Bi(2-7)(+), Bi(3, 5)(2+)) bombardment, and spectral information and general rules for the fragmentation pattern are presented. Evidence for hydrogen bonding, due to high molecular secondary cluster ions, could be found. Hydrogen bonding strength could be estimated by ToF-SIMS via correlation of the anionic yield enhancement with solvent parameters.

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Section: Mass Spectra -Fragmentation Patternsupporting

confidence: 88%

Investigation of ionic liquids under Bi‐ion and Bi‐cluster ions bombardment by ToF‐SIMS

2010

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“…Clusters of the type [(DAI) 2 (AlCl 4 )] + (DAI= 1,3-dialkylimidazolium cation) have been observed in organo-aluminate molten salts under conditions of fast atom bombardment mass spectrometry (FAB-MS). 47 Moreover, electron spray mass spectrometry experiments in both positive and negative modes (ESI(+) and ESI(-)) of various 1,3-dialkylimidazolium cations associated with different anions show also the formation of supramolecular structures of the type [(DAI) x …”

Section: Structural Organization In Liquid and Gas Phasementioning

confidence: 99%

On the solid, liquid and solution structural organization of imidazolium ionic liquids

Dupont¹

2004

J. Braz. Chem. Soc.

816

648

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Sais derivados do cátion 1,3-dialquilimidazólio são uma das mais populares e investigadas classes de líquidos iônicos a temperatura ambiente. Embora, em vários casos, suas propriedades físico-químicas e/ou o resultado dos processos que ocorrem nesses líquidos diferem significantemente daqueles obtidos em solventes orgânicos dipolares, estes ainda podem ser descritos como simples solventes orgânicos. Nesta revisão, será introduzido o conceito que líquidos iônicos derivados do cátion 1,3-dialquilimidazólio são mais convenientemente descritos como estruturas poliméricasn-} n onde DAI representa o cátion 1,3-dialquilimidazólio e X o ânion. Este padrão estrutural é observado geralmente em sólidos e mantido em grande extensão no estado líquido e mesmo em fase gasosa. A introdução de outras moléculas ou macromoléculas no líquido iônico provoca a perturbação da rede de ligações de hidrogênios podendo gerar, em alguns casos, nano-estruturas com regiões polares e apolares onde compostos de inclusão podem ser formados.

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“…All three ring protons H2, H4, and H5, see Fig. 2, form strong hydrogen bonds to e.g., halide ions [60][61][62][63][64][65]. From measurement of the 13 C dipole-dipole relaxation rate, Huang et al [66] found that the hydrogen atom attached to the ring C2 is hydrogen bonded to the [BF 4 ]…”

Section: N]mentioning

confidence: 99%

“…The structural analysis helps the understanding of solvation of nonpolar, polar, and associating solutes in these media [140,148]. The existence of an extended hydrogen-bonded network structure was suggested by Abdul-Sada et al [65] for 1-alkyl-3-methylimidazolium halides based on results from fast-atom bombardment mass spectroscopy. Charge ordering in RTILs was discussed by Hardacre et al [111,112].…”

Section: Local Structures In Ionic Liquidsmentioning

confidence: 99%

Raman Spectroscopy and Ab-Initio Model Calculations on Ionic Liquids

2007

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Summary.A review of the recent developments in the study and understanding of room temperature ionic liquids are given. An intimate picture of how and why these liquids are not crystals at ambient conditions is attempted, based on evidence from crystallographical results combined with vibrational spectroscopy and ab-initio molecular orbital calculations. A discussion is given, based mainly on some recent FT-Raman spectroscopic results on the model ionic liquid system of 1-butyl-3-methylimidazolium ([C 4 mim][X]) salts. The rotational isomerism of the [C 4 mim] þ cation is described: the presence of anti and gauche conformers that has been elucidated in remarkable papers by Hamaguchi et al. Such presence of a conformational equilibrium seems to be a general feature of the room temperature liquids. Then the ''localized structure features'' that apparently exist in ionic liquids are described. It is hoped that the structural resolving power of Raman spectroscopy will be appreciated by the reader. It is of remarkable use on crystals of known different conformations and on the corresponding liquids, especially in combination with modern quantum mechanics calculations. It is hoped that these interdisciplinary methods will be applied to many more systems in the future. A few examples will be discussed.

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Letter: Evidence for the clustering of substituted imidazolium salts via hydrogen bonding under the conditions of fast atom bombardment mass spectrometry

Cited by 47 publications

References 0 publications

Investigation of ionic liquids under Bi‐ion and Bi‐cluster ions bombardment by ToF‐SIMS

Investigation of ionic liquids under Bi‐ion and Bi‐cluster ions bombardment by ToF‐SIMS

On the solid, liquid and solution structural organization of imidazolium ionic liquids

Raman Spectroscopy and Ab-Initio Model Calculations on Ionic Liquids

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