FT-IR and FT-Raman spectroscopies and DFT modelling of benzimidazolium salts

Malek, Kamilla; Puc, Agnieszka; Schroeder, Grzegorz; Рыбаченко, В. И.; Proniewicz, Leonard M.

doi:10.1016/j.chemphys.2006.05.021

Cited by 38 publications

(26 citation statements)

References 34 publications

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“…The experimental bands were assigned to normal modes on the basis of potential energy distribution analysis. Good agreements between the calculated and observed frequencies were obtained [24].…”

Section: Other Systemsmentioning

confidence: 68%

“…The molecular vibrations of polycrystalline 1,3-dimethylbenzimidazolium chlorate(VII) and 1,3-di-1-adamantylbenzimidazolium chlorate(VII) have been investigated by FTIR and FT-Raman spectroscopy [24]. Also for these compounds, DFT methods (B3LYP) were used to determine the geometrical and vibrational characteristics of these salts.…”

Section: Other Systemsmentioning

confidence: 99%

“…1. However, also other possibilities exist and have been investigated, like pyrrolidinium [17][18][19][20], guanidinium [21,22], 1,3-diazolium [23], or benzimidazolium [24] salts. In particular, the 1-alkyl-3-methylimidazolium salts are an interesting and useful class of room temperature ionic liquids.…”

Section: Introduction To Room Temperature Ionic Liquidsmentioning

confidence: 99%

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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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Section: Other Systemsmentioning

confidence: 68%

Section: Other Systemsmentioning

confidence: 99%

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Raman Spectroscopy and Ab-Initio Model Calculations on Ionic Liquids

2007

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“…For 5-nitro-2-(4-nitrobenzyl) benzoxazole C-N stretching vibrations are observed in the region 1228-1195 cm À1 [54]. C-N stretching modes are reported at 1268, 1220, 1151 cm À1 theoretically for benzimidazolium salts by Malek et al [38].…”

Section: Ir and Raman Spectramentioning

confidence: 90%

“…Minitha et al [36] reported tN-H at 3469 cm À1 , dN-H at 1300 cm À1 and cN-H at 455 cm À1 . Kim et al reported [37] N-H deformation bands at 549, 1484 cm À1 in the Raman spectrum and at 556, 1495 cm À1 theoretically for benzimidazole and Malek et al [38] reported modes at 1394, 680 cm À1 theoretically as N-H deformation modes.…”

Section: Ir and Raman Spectramentioning

confidence: 96%

Spectroscopic and theoretical characterization of 2-(4-methoxyphenyl)-4,5-dimethyl-1H-imidazole 3-oxide

Benzon

Varghese

Panicker³

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Robust alkyl‐bridged bis(N‐heterocyclic carbene)palladium(II) complexes anchored on Merrifield's resin as active catalysts for the selective synthesis of flavones and alkynones

Mansour

Fettouhi

Saleem

et al. 2021

Applied Organom Chemis

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Highly active and efficient propylene‐bridged bis(N‐heterocyclic carbene)palladium(II) complexes covalently anchored on Merrifield's resin were synthesized and characterized using various physical and spectroscopic techniques. The two anchored Pd(II) complexes consist of the system: Merrifield's resin‐linker‐bis(NHC)Pd(II), the linkers being benzyl and benzyl‐O‐(CH2)3 for (Pd‐NHC1@M) and (Pd‐NHC2@M), respectively. The short linker anchored bis‐benzimidazolium ligand precursor (PBBI‐1@M) was synthesized via direct carbon–nitrogen alkylation of a propylene‐bridged bis(benzimidazole) (PBBI‐1) by Merrifield's resin chlorobenzyl group. The longer linker anchored bis‐benzimidazolium ligand precursor (PBBI‐2@M) was obtained in a two‐step reaction involving first alkylation of (PBBI‐1) with 3‐chloro‐1‐propanol followed by a nucleophilic substitution at Merrifield's resin chlorobenzyl group. Both supported ligand precursors (PBBI‐1@M and PBBI‐2@M) reacted with palladium acetate to produce the two heterogeneous catalysts (Pd‐NHC1@M) and (Pd‐NHC2@M). 13C NMR palladation shift of the benzimidazole N–C–N (C2) carbon was found very similar in both the liquid NMR spectra of the homogeneous complexes and the CP/MASS spectra of the corresponding covalently anchored complexes. The catalytic activity, stability, and the recycling ability of the supported catalysts have been investigated in the carbonylative Sonogashira coupling reactions of aryl iodides with aryl alkynes and alkyl alkynes and also in the cyclocarbonylative Sonogashira coupling reactions of aryl iodides with aryl alkynes via one pot reactions. The longer linker catalyst Pd‐NHC2@M demonstrated excellent catalytic activity, stability, and very high recycling ability in the two carbonylative coupling reactions. These systems exhibit the hypothesized thermodynamic stability offered by the chelate effect in addition to the strong sigma donor ability of a bis(NHC) ligand system generating electron‐rich palladium centers that favor the oxidative addition step of the aryl halide.

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FT-IR and FT-Raman spectroscopies and DFT modelling of benzimidazolium salts

Cited by 38 publications

References 34 publications

Raman Spectroscopy and Ab-Initio Model Calculations on Ionic Liquids

Raman Spectroscopy and Ab-Initio Model Calculations on Ionic Liquids

Spectroscopic and theoretical characterization of 2-(4-methoxyphenyl)-4,5-dimethyl-1H-imidazole 3-oxide

Robust alkyl‐bridged bis(N‐heterocyclic carbene)palladium(II) complexes anchored on Merrifield's resin as active catalysts for the selective synthesis of flavones and alkynones

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