New N-methylimidazolium hexachloroantimonate: Synthesis, crystal structure, Hirshfeld surface and catalytic activity of in cyclopropanation of stryrene
[en] The N-methylimidazolium hexachloroantimonate salt Cl6Sb·C4H7N2 (MIMSb), was prepared and fully characterized. In 1H NMR spectrum, the N-H proton shifted to downfield because of the presence of SbCl6− and appears as a triplet at 13.19 ppm. Characterization with IR spectroscopy shows strong absorption band at around 699 cm−1 which is attributed to Sb−Cl stretching. Furthermore, UV–visible analysis at high concentrations in DMSO suggested that MIMSb interacts with DMSO leading to an absorption in visible region at λmax of 426 nm. Electrochemical characterization using cyclic voltammetry demonstrates three redox processes with reduction peaks at 0.69, −0.13 and −0.50 V. Finally, molecular structure of the product was determined by X-ray diffraction analysis. The crystal structure determination was carried out with Mo-Kα X-ray and data measured at 100 K. The title compound crystallizes in monoclinic P21/c space group with unit cell parameters a = 7.1131 (5) Å, b = 12.4436 (9) Å, c = 14.1658 (11) Å, V = 1241.86 (16) Å3 and Z = 4. The crystal packing is stabilized by H---Cl interaction. The analysis of intermolecular interactions was realized through the mapping of contact descriptors dnorm, shape-index and the fingerprint reveling that the most significant contribution to the Hirshfeld surface (69.4%) is from H---Cl contacts. Finally, the catalytic activity of MIMSb was probed in the cyclopropanation of styrene with ethyl diazoacetate.
Disciplines :
Chemistry
Author, co-author :
Etse, Koffi Senam ; Université de Liège - ULiège > Département de pharmacie > Chimie analytique
Mahmoud, Abdelfattah ; Université de Liège - ULiège > Département de chimie (sciences) > LCIS - GreenMAT
Language :
English
Title :
New N-methylimidazolium hexachloroantimonate: Synthesis, crystal structure, Hirshfeld surface and catalytic activity of in cyclopropanation of stryrene
Chiappe, C., Pieraccini, D., Ionic liquids: solvent properties and organic reactivity (2005) J. Phys. Org. Chem., 18 (4), pp. 275-297
Zheng, D., Dong, L.I., Huang, W., Wu, X., Nie, N., A review of imidazolium ionic liquids research and development towards working pair of absorption cycle (2014) Renew. Sustain. Energy Rev., 37, pp. 47-68
Chong, A.L., Forsyth, M., MacFarlane, D.R., Novel imidazolinium ionic liquids and organic salts (2015) Electrochim. Acta, 159, pp. 219-226
Dzyuba, S.V., Bartsch, R.A., (2001), https://doi.org/10.1002/jhet.5570380139, Efficient synthesis of 1-alkyl(aralkyl)-3-methyl(ethyl)imidazolium halides: Precursors for room-temperature ionic liquids, J. Heterocycl. Chem. 38 265–268
Welton, T., Room-temperature ionic liquids. Solvents for synthesis and catalysis (1999) Chem. Rev., 99 (8), pp. 2071-2084
Wilkes, J., Properties of ionic liquid solvents for catalysis (2004) J. Mol. Catal. A: Chem., 214 (1), pp. 11-17
Elango, K., Srirambalaji, R., Anantharaman, G., Synthesis of N-alkylimidazolium salts and their utility as solvents in the Beckmann rearrangement (2007) Tetrahedron Lett., 48 (51), pp. 9059-9062
McEwen, A.B., Ngo, H.L., LeCompte, K., Goldman, J.L., Electrochemical properties of imidazolium salt electrolytes for electrochemical capacitor applications (1999) J. Electrochem. Soc., 146 (5), pp. 1687-1695
Çoban, E.P., Fırıncı, R., Biyik, H., Günay, M.E., Unsymmetrically substituted imidazolium salts: Synthesis, characterization and antimicrobial activity (2017) Brazilian J. Pharm. Sci., 53, pp. 1-10
Riduan, S.N., Zhang, Y., Imidazolium salts and their polymeric materials for biological applications (2013) Chem. Soc. Rev., 42 (23), p. 9055
Lee, S.-G., Functionalized imidazolium salts for task-specific ionic liquids and their applications (2006) Chem. Commun., (10), p. 1049
Cho, H.C., Lee, H.S., Chun, J., Lee, S.M., Kim, H.J., Son, S.U., Tubular microporous organic networks bearing imidazolium salts and their catalytic CO 2 conversion to cyclic carbonates (2011) Chem. Commun., 47 (3), pp. 917-919
Thierry, M., Majira, A., Pégot, B., Cezard, L., Bourdreux, F., Clément, G., Perreau, F., Cottyn, B., Imidazolium-based ionic liquids as efficient reagents for the C−O bond cleavage of lignin (2018) ChemSusChem, 11 (2), pp. 439-448
Chen, J., Xiong, X., Chen, Z., Huang, J., Imidazolium salt catalyzed para-selective halogenation of electron-rich arenes (2015) Synlett, 26 (20), pp. 2831-2834
Kumar, M.R., Park, K., Lee, S., Synthesis of amido-N-imidazolium salts and their applications as ligands in Suzuki-Miyaura reactions: Coupling of hetero- aromatic halides and the synthesis of milrinone and irbesartan (2010) Adv. Synth. Catal., 352 (18), pp. 3255-3266
Olivier-Bourbigou, H., Magna, L., Morvan, D., Ionic liquids and catalysis: Recent progress from knowledge to applications (2010) Appl. Catal. A, 373 (1-2), pp. 1-56
Cavell, K., N-Heterocyclic carbenes/imidazolium salts as substrates in catalysis: the catalytic 2-substitution and annulation of heterocyclic compounds (2008) Dalton Trans., (47), p. 6676
Herrmann, W.A., N-Heterocyclic carbenes: A new concept in organometallic catalysis13 (2002) Angew. Chemie Int. Ed., 41, pp. 1290-1309
Deetlefs, M., Seddon, K.R., Shara, M., Predicting physical properties of ionic liquids (2006) Phys. Chem. Chem. Phys., 8 (5), pp. 642-649
Pereiro, A.B., Legido, J.L., Rodrı́guez, A., Physical properties of ionic liquids based on 1-alkyl-3-methylimidazolium cation and hexafluorophosphate as anion and temperature dependence (2007) J. Chem. Thermodyn., 39 (8), pp. 1168-1175
Zhang, S., Sun, N., He, X., Lu, X., Zhang, X., Physical properties of ionic liquids: database and evaluation (2006) J. Phys. Chem. Ref. Data, 35 (4), pp. 1475-1517
Lungwitz, R., Spange, S., Determination of hydrogen-bond-accepting and -donating abilities of ionic liquids with halogeno complex anions by means of 1 H NMR spectroscopy (2012) ChemPhysChem, 13 (7), pp. 1910-1916
Ozokwelu, D., Zhang, S., Okafor, O.C., Cheng, W., Litombe, N., Ozokwelu, D., Zhang, S., Litombe, N., Preparation and characterization of ionic liquids (2017) Nov. Catal. Sep. Process. Based Ion. Liq., pp. 13-44
Hahn, F.E., Jahnke, M.C., Heterocyclic carbenes: synthesis and coordination chemistry (2008) Angew. Chem. Int. Ed., 47 (17), pp. 3122-3172
Gridnev, A.A., Mihaltseva, I.M., Synthesis of 1-alkylimidazoles (1994) Synth. Commun., 24 (11), pp. 1547-1555
McIntosh, A.J.S., Griffith, J., Gräsvik, J., Methods of synthesis and purification of ionic liquids (2016) Appl. Purification, Recover. Ion. Liq., pp. 59-99
Kabuß, S., Alkylations by dialkoxycarbonium salts (1966) Angew. Chem. Int. Ed. Engl., 5 (7), pp. 675-676
Oishi, T., Kamata, K., Ban, Y., Activation of weak organic bases: the alkylation of NN-disubstituted sulphonamides (1970) J. Chem. Soc. D, (12), p. 777
Dimroth, K., Heinrich, P., Aryl-substituted dialkoxycarbonium ions as alkylating agents (1966) Angew. Chem. Int. Ed. Engl., 5 (7). , 676–676
Jonek, M., Makhloufi, A., Ganter, C., An N-heterocyclic carbene with a sulfonamide group embedded within the heterocyclic backbone (2017) J. Organomet. Chem., 838, pp. 37-41
Perrin, D.D., Armarego, W.L.F., https://doi.org/10.1002/recl.19881071209, Purification of Laboratory Chemicals, third ed., Pergamon Press, Oxford, England, 1988
Fulmer, G.R., Miller, A.J.M., Sherden, N.H., Gottlieb, H.E., Nudelman, A., Stoltz, B.M., Bercaw, J.E., Goldberg, K.I., NMR chemical shifts of trace impurities: common laboratory solvents, organics, and gases in deuterated solvents relevant to the organometallic chemist (2010) Organometallics, 29 (9), pp. 2176-2179
Etsè, K.S., Boschini, F., Karegeya, C., Roex, E., Zaragoza, G., Demonceau, A., Cloots, R., Mahmoud, E., (2020), https://doi.org/10.1016/j.electacta.2020.135659, Exploring organo-palladium(II) complexes as novel organometallic materials for Li-ion batteries, Electrochim. Acta 337 135659
(2004), Bruker, APPEX_II, Bruker, AXS Inc., Madison, Wisconsin, USA
Farrugia, L.J., WinGX and ORTEP for windows: an update (2012) J. Appl. Cryst., 45, pp. 849-854
Macrae, C.F., Bruno, I.J., Chisholm, J.A., Edgington, P.R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Wood, P.A., Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures (2008) J. Appl. Crystallogr., 41 (2), pp. 466-470
Matsumoto, K., Hagiwara, R., Yoshida, R., Ito, Y., Mazej, Z., Benkič, P., Žemva, B., Matsubara, S., Syntheses, structures and properties of 1-ethyl-3-methylimidazolium salts of fluorocomplex anions (2004) Dalton Trans., (1), pp. 144-149
Chiappe, C., Rajamani, S., D'Andrea, F., A dramatic effect of the ionic liquid structure in esterification reactions in protic ionic media (2013) Green Chem., 15 (1), pp. 137-143
Yoshizawa, M., Xu, W., Angell, C.A., Ionic liquids by proton transfer: Vapor pressure, conductivity, and the relevance of ΔpKa from aqueous solutions (2003) J. Am. Chem. Soc., 125, pp. 15411-15419
Ohno, H., Yoshizawa, M., Ion conductive characteristics of ionic liquids prepared by neutralization of alkylimidazoles (2002) Solid State Ionics, 154-155, pp. 303-309
Hirao, M., Sugimoto, H., Ohno, H., Preparation of novel room-temperature molten salts by neutralization of amines (2000) J. Electrochem. Soc., 147 (11), p. 4168
Greaves, L.T., Drummond, C.J., Protic ionic liquids: Properties and applications (2008) Chem. Rev., 108, pp. 206-237
Weng, W., Zhang, Z., Schlueter, J.A., Amine, K., Synthesis and electrochemical property of sulfone-functionalized imidazolium ionic liquid electrolytes (2013) Electrochim. Acta, 92, pp. 392-396
Bourissou, D., Guerret, O., Gabbaï, F.P., Bertrand, G., Stable carbenes (2000) Chem. Rev., 100 (1), pp. 39-92
Reisenauer, H.P., Romanski, J., Mloston, G., Schreiner, P.R., Dimethoxycarbene: Conformational analysis of a reactive intermediate (2006) Eur. J. Org. Chem., 2006 (21), pp. 4813-4818
Etsè, K.S., Dassonneville, B., Zaragoza, G., Demonceau, A., One-pot, Pd/Cu-catalysed synthesis of alkynyl-substituted 3-ylidene-dihydrobenzo[ d ]isothiazole 1,1-dioxides (2017) Tetrahedron Lett., 58 (8), pp. 789-793
Robinson, K., Gibbs, G.V., Ribbe, P.H., Quadratic elongation: A quantitative measure of distortion in coordination polyhedra (1971) Science, 172 (3983), pp. 567-570
Imai, Y.N., Inoue, Y., Nakanishi, I., Kitaura, K., Cl-π interactions in protein-ligand complexes (2008) Protein Sci., 17 (7), pp. 1129-1137
Dong, K., Zhang, S., Wang, J., Understanding the hydrogen bonds in ionic liquids and their roles in properties and reactions (2016) Chem. Commun., 52 (41), pp. 6744-6764
Reichert, W.M., Holbrey, J.D., Swatloski, R.P., Gutowski, K.E., Visser, A.E., Nieuwenhuyzen, M., Seddon, K.R., Rogers, R.D., Solid-state analysis of low-melting 1,3-dialkylimidazolium hexafluorophosphate salts (ionic liquids) by combined X-ray crystallographic and computational analyses (2007) Cryst. Growth Des., 7 (6), pp. 1106-1114
Matsumoto, K., Hagiwara, R., Mazej, Z., Benkič, P., Žemva, B., Crystal structures of frozen room temperature ionic liquids, 1-ethyl-3-methylimidazolium tetrafluoroborate (EMImBF4), hexafluoroniobate (EMImNbF6) and hexafluorotantalate (EMImTaF6), determined by low-temperature X-ray diffraction (2006) Solid State Sci., 8 (10), pp. 1250-1257
(2017), D.J. and M.A.S. M.J. Turner, J.J. McKinnon, S.K. Wolff, D.J. Grimwood, P.R. Spackman, CrystalExplorer17, University of Western Australia
Spackman, M.A., Jayatilaka, D., Hirshfeld surface analysis (2009) CrystEngComm, 11 (1), pp. 19-32
Etse, K.S., Zaragoza, G., Pirotte, B., (2019), https://doi.org/10.5155/eurjchem.10.3.189-194.1903, Crystal structure and Hirshfeld surface analysis of N-(2-(N-methylsulfamoyl)phenyl)formamide: Degradation product of 2-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide, Eur. J. Chem. 10 189-194
Phan, C.U., Shen, J., Liu, J., Mao, J., Hu, X., Tang, G., Isomorphous crystals formed by the similar supramolecular motifs in sorafenib hydrochloride and regorafenib hydrochloride salts (2019) Crystals, 9 (12), p. 649