Abstract
The notable nowadays physical-chemical structures as ionic liquids (ILs) are, due to their versatility properties adjusted by changing either the anion or cation sides, with spread applications as solvents (viz. organic reaction, bio- and nano-catalysis, polymerization), electrolytes (viz. fuel cells, batteries and sensors), lubricants and additives (including fuel additives), or in chemical engineering including separation (gas chromatography/GC-head space solvents, gas separation, membranes extraction, extractive distillation), heat storage (as thermal fluids), till the nano-technology (protein crystallization, liquids crystals and their use in monitor displays, robotics and artificial muscles), just to name few, are in the present chapter reviewed from the scientific generations created with their structural consequences; they are then used as the compounds for which the recently predicted bondon as the quantum quasi-particle of chemical bonding may be identified in the allied Raman/IR spectra through a specific algorithm involving the bondonic quantum numbers prediction in spectra and of their most tangible quantum appearance; this because the invariable four-levels for bondonic formations confirms the quantum entangled states associated with their existences, as just noted by Putz and Ori 2015, see Chap. 10 of the same monograph, while the objective realization associates either with IR or Raman of IL computed spectra; connection with experimental recorded IR spectra is also presented with encouragement perspective for bondonic observation, while correlation with eco-toxicological data (EC50) is equally presented and interpreted from a bondonic sub-atomic perspective.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Abrusci C, Palomar J, Pablos JL, Rodriguez F, Catalina F (2011) Efficient biodegradation of common ionic liquids by Sphingomonas paucimobilis bacterium. Green Chem 13:709–717
Allen CR, Richard PL, Ward AJ, van de Water LGA, Masters AF, Maschmeyer T (2006) Facile synthesis of ionic liquids possessing chiral carboxylates. Tetrahedron Lett 47(41):7367–7370
Anthony L, Maginn EJ, Brennecke JF (2001) Solution thermodynamics of Imidazolium-Based Ionic liquids and water. J Phys Chem B 105(44):10942–10949
Anthony JL, Maginn EJ, Brennecke JF (2002) Solubilities and thermodynamic properties of gases in the ionic liquid 1-n-Butyl-3-methylimidazolium hexafluorophosphate. J Phys Chem B 106(29):7315–7320
Appetecchi GB, Montanino M, Zane D, Carewska M, Alessandrini F, Passerini S (2009) Effect of the alkyl group on the synthesis and the electrochemical properties of N-alkyl-N-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide ionic liquids. Electrochim Acta 54:1325–1332
Boethling RS (1994) Cationic surfactants. In: Cross J, Singer EJ (Eds) Surfactant science series, vol 53. Marcus Dekker, New York; pp 95–135
Bremen University Data Base (2014) http://www.il-eco.uft.uni-bremen.de/. Accessed July 2014
Calvano CD, Ceglie CD, D’Accolti L, Zambonin CG (2012) MALDI-TOF mass spectrometry detection of extra-virgin olive oil adulteration with hazelnut oil by analysis of phospholipids using an ionic liquid as matrix and extraction solvent. Food Chem 134(2):1192–1198
Carrera GVSM, Frade RFM, Aires-De-Sousa J, Afonso CAM, Branco LC (2010) Synthesis and properties of new functionalized guanidinium based ionic liquids as non-toxic versatile organic materials. Tetrahedron 66(45):8785–8794
Cheetham AK, Day P (1987) Solid state chemistry—techniques (Chap. 9). Clarendon Press, Oxford
Chemical Book (2014) http://www.chemicalbook.com/. Accessed July 2014
Cho CW, Jeon YC, Pham TP, Vijayaraghavan K, Yun YS (2008) The ecotoxicity of ionic liquids and traditional organic solvents on microalga Selenastrum capricornutum. Ecotoxicol Environ Saf 71(1):166–171
Coleman D, Gathergood N (2010) Biodegradation studies of ionic liquids Chem Soc Rev 39:600–637
Compton A (1923) A quantum theory of the scattering of X-rays by light elements. Phys Rev 21:483
Costa Gomes MF (2007) Low-pressure solubility and thermodynamics of solvation of carbon dioxide, ethane, and hydrogen in 1-Hexyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)-amide between temperatures of 283 and 343 K. J Chem Eng Data 52:472–475
Couling DJ, Bernot RJ, Docherty KM, Dixon JK, Maginn EJ (2006) Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure-property relationship modeling. Green Chem 8:82–90
Deng Y, Morrissey S, Gathergood N, Delort A-M, Husson P, Costa Gomes MF (2010) The presence of functional groups key for biodegradation in ionic liquids: effect on gas solubility. ChemSusChem 3:377–385
Deng Y, Husson P, Delort A-M, Besse-Hoggan P, Sancelme M, Costa Gomes MF (2011) Influence of an oxygen functionalization on the physicochemical properties of ionic liquids: density, viscosity, and carbon dioxide solubility as a function of temperature. J Chem Eng Data 56(11):4194–4202
Deng Y, Besse-Hogganb P, Hussona P, Sancelme M, Delortb AM, Stepnowskic P, Paszkiewiczc M, Gołębiowskic M, Costa Gomes MF (2012) Relevant parameters for assessing the environmental impact of some pyridinium, ammonium and pyrrolidinium based ionic liquids. Chemosphere 89(3):327–333
Docherty K, Kulpa C (2005) Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids. Green Chem 7:185–189
Docherty KM, Dixon JK, Kulpa CF (2007) Biodegradability of imidazolium and pyridinium ionic liquids by an activated sludge microbial community. Biodegradation 18:481–493
Docherty KM, Joyce MV, Kulacki KJ, Kulpa CF (2010) Novel microbial biodegradation and metabolite toxicity of three Pyridinium-Cation ionic liquids. Green Chem 12:701–712
Energy Units Converter (2014) http://www.colby.edu/chemistry/PChem/Hartree.html. Accessed July 2014
Farmer VC (1974) The infrared spectra of minerals. Monograph, no. 4. Mineralogical Society of London, London
Ferraz R, Branco LC, Prudêncio C, Noronha JP, Petrovski Ž (2011) Ionic liquids as active pharmaceutical ingredients. ChemMedChem 6(6):975–985
Florindo C, Araújo JMM, Alves F, Matos C, Ferraz R, Prudêncio C, Noronha JP, Petrovski Ž, Branco L, Rebelo LPN, Marrucho IM (2013) Evaluation of solubility and partition properties of ampicillin-based ionic liquids Int. J Pharm 456(2):553–559
Ford L, Harjani JR, Atefi F, Garcia MT, Singer RD, Scammells PJ (2010) Further studies on the biodegradation of ionic liquids. Green Chem 12: 1783–1789
Frade RFM, Afonso CAM (2010) Impact of ionic liquids in environment and humans: an overview. Hum Exp Toxicol 29(12):1038–1054
Freeman S (1974) Applications of laser Raman spectroscopy. Wiley, New York
Fukumoto K, Yoshizawa M, Ohno H (2005) Room temperature ionic liquids from 20 natural aminoacids. J Am Chem Soc 127:2398–2399
Gao H, Zhang Y, Wang HJ, Liu J, Chen J (2010) Theoretical study on the structure and cation-anion interaction of amino acid cation based amino acid ionic liquid [Pro] + [NO3]−. J Phys Chem A 114(37):10243–10252
Garcia MT, Gathergood N, Scammells PJ (2005) Green Chem 7:9–14
Gathergood N, Scammells PJ (2002) Design and preparation of room-temperature ionic liquids containing biodegradable side chains. Aust J Chem 55:557–560
Gathergood N, Garcia MT, Scammells PJ (2004) Green Chem 6:166–175
Gathergood N, Scammells PJ, Garcia MT (2006) Biodegradable ionic liquids. Part III: the first readily biodegradable ionic liquids. Green Chem 8:156–160
Harjani JR, Singer RD, Garcia MT, Scammells PJ (2008) Green Chem 4:436–438
Harjani JR, Singer RD, Garciac MT, Peter J (2009) Scammells biodegradable pyridinium ionic liquids: design, synthesis and evaluation. Green Chem 11:83–90.
Heitler W (1954) The quantum theory of radiation, 3rd ed. Cambridge University Press: New York
Hussey CL (1983) Room temperatures molten salt systems. Adv Molten Salt Chem 5:185–229
Hough WL, Smiglak M, Rodríguez H, Swatloski RP, Spear SK, Daly DT, Pernak J, Grisel JE, Carliss RD, Soutullo MD, Davis JH, Rogers Jr RD (2007) The third evolution of ionic liquids: active pharmaceutical ingredients. New J Chem 31:1429–1436
Howard PH, Boethling RS, Stiteler W, Meylan W, Beauman J (1991) Sci Total Environ 635:109–110
HyperChem (2002) Hypercube Inc. 7.01 [Program package]
Imperato G, König B, Chiappe C (2007) Ionic green solvents from renewable resources. Eur J Org Chem 7:1049–1058
Jastorff B, Molter K, Behrend P, Weber UB, Filser J, Heimers A, Ondruschka B, Ranke J, Schaefer M, Schroder H, Stark A, Stepnowski P, Stock F, Störmann R, Stolte S, Biermann UW, Ziegert S, Thoming J (2005) Green Chem 7:362–372
Kendall DN (1966) Applied infrared spectroscopy. Reinhold Publishing Corporation, NY
Koke S, Grebing C, Frei H, Anderson A, Assion A, Steinmeyer G (2010) Direct frequency comb synthesis with arbitrary offset and shot-noise-limited phase noise. Nat Photonics 4:462–465
Kumar RA, Papaïconomou N, Lee JM, Salminen J, Clark DS, Prausnitz JM (2009) In vitro cytotoxicities of ionic liquids: effect of cation rings, functional groups, and anions. Environ Toxicol 24(4):388–95
Landsberg G., Mandelstam L. (1928) A novel effect of light scattering in crystals. Naturwissenschaften 16:557
Latala A, Nedzi M, Stepnowski P (2010) Toxicity of imidazolium ionic liquids towards algae. Influence of salinity variations. Green Chem 12: 60–64
Li Y, Li G, Wang X, Zhu Z, Ma H, Zhang T, Jin J (2012) Poly(ionic liquid)-wrapped single-walled carbon nanotubes for sub-ppb detection of CO2. Chem Commun 48:8222–8224
Mallakpour S, Rafiee Z (2011a) Ionic liquids as environmentally friendly solvents in macromolecules chemistry and technology, Part I. J Polym Environ 19:447–484
Mallakpour S, Rafiee Z (2011b) Ionic liquids as environmentally friendly solvents in macromolecules chemistry and technology, Part II. J Polym Environ 19:485–517
Marciniak A (2010) The solubility parameters of ionic liquids. Int J Mol Sci 11(5):1973–1990
Marrucho IM, Branco LC, Rebelo LP (2014) Ionic liquids in pharmaceutical applications. Annu Rev Chem Biomol Eng 5:527–546
McMillian PF, Hofmeister A (1988) Infrared and Raman spectroscopy. In: Hawthorne FC (ed) Spectroscopic methods in mineralogy and geology. Reviews in mineralogy, vol 18. Mineralogical Society of America, USA, pp 99–159
Metric Converter (2014) http://www.ecoterr.com/length_units_metric_standard_calculator.htm. Accessed July 2014
Mohajeri A, Ashrafi A (2011) Structure and electronic properties of amino acid ionic liquids. J Phys Chem A 115(24):6589–6593
Mu X, Qi L, Zhang H, Shen Y, Qiao J, Ma H (2012) Ionic liquids with amino acids as cations: novel chiral ligands in chiral ligand-exchange capillary electrophoresis. Talanta 97:349–354
Muldoon MJ, Aki SNVK, Anderson JL, Dixon JK, Brennecke JF (2007) Improving carbon dioxide solubility in ionic liquids. J Phys Chem B 111:9001–9009
Nakamoto K (1986) Infrared and Raman spectra of inorganic and coordination compounds. Wiley, New York
Ohno H, Fukumoto K. (2007) Amino acid ionic liquids. Acc Chem Res 40:1122–1129
Ohno H, Yoshizawa M, Mizumo T (2005) In: Ohno H (Ed) Electrochemical aspects of ionic liquids. Wiley, Hoboken, pp 75–81
Palomar J, Torrecilla JS, Lemus J, Ferro VR, Rodriguez F (2010) Phys Chem Chem Phys 12:1991–2000
Papaiconomou N, Salminen J, Lee J-M, Prausnitz JM (2007) Physicochemical properties of hydrophobic ionic liquids containing 1-Octylpyridinium, 1-Octyl-2-methylpyridinium, or 1-Octyl-4-methylpyridinium Cations. J Chem Eng Data 52:833–840
Papaiconomou N, Estager J, Traore Y, Bauduin P, Bas C, Legeai S, Viboud S, Draye M (2010) Synthesis, physicochemical properties, and toxicity data of new hydrophobic ionic liquids containing dimethylpyridinium and trimethylpyridinium cations. J Chem Eng Data 55:1971–1979
Patrascu C, Sugisaki C, Mingotaud C, Marty J-D, Genisson Y, Lauth-de Viguerie N (2004) New pyridinium chiral ionic liquids. Heterocycles 63(9):2033–2041
Pernak J, Syguda A, Janiszewska D, Materna K, Praczyk T (2011) Ionic liquids with herbicidal anions. Tetrahedron 67:4838–4844
Petkovic M, Seddon KR, Rebelo LPN, Pereira CS (2011) Ionic liquids: a pathway to environmental acceptability Chem Soc Rev 40:1383–1403
Pham TPT, Cho C-W, Jeon C-O, Chung Y-J, Lee M-W, Yun Y-S (2009) Identification of metabolites involved in the biodegradation of the ionic liquid 1-butyl-3-methylpyridinium bromide by activated sludge microorganisms. Environ Sci Technol 43:516–521
Pham TPT, Cho C-W, Yun Y-S (2010) Environmental fate and toxicity of ionic liquids: a review. Water Res 44:352–372
Praczyk T, Kardasz P, Jakubiak E, Syguda A, Materna K, Pernak J (2012) Herbicidal ionic liquids with 2, 4-D. Weed Sci 60(2):189–192
Pretti C, Chiappe C, Baldetti I, Brunini S, Monni G, Intorre L. (2009) Acute toxicity of ionic liquids for three freshwater organisms: pseudokirchneriella subcapitata, Daphnia magna and Danio rerio Ecotoxicol. Environ Saf 72(4):1170–1176
Putz MV (2010a) The bondons: the quantum particles of the chemical bond. Int J Mol Sci 11(11):4227–4256
Putz MV (2010b) Beyond quantum nonlocality: chemical bonding field. Int J Environ Sci 1: 25–31
Putz MV (2012a) Quantum theory: density, condensation, and bonding. Apple Academics, Toronto
Putz MV (2012b) Chemical orthogonal spaces, in mathematical chemistry monographs, vol 14. University of Kragujevac, Kragujevac
Putz MV (ed) (2012c) QSAR & SPECTRAL-SAR in computational Ecotoxicology. Apple Academics, Toronto; CRC Press–—Taylor & Francis Group, New Jersey
Putz MV (2013) Quantum and optical dynamics of matter for nanotechnology. IGI Global, Hershey
Putz MV (2015a) Quantum nanochemistry, vol 3 (Quantum molecules and reactivity). Apple Academics Press, Toronto
Putz MV (2015b) Quantum nanochemistry, vol 4 (Quantum solids and orderability). Apple Academics Press, Toronto
Putz MV (2015c) Quantum nanochemistry, vol. 3 (Quantum molecule and reactivity) & vol. 5 (Quantum structure-activity relationships). Apple Academics Press, Toronto
Putz AM, Putz MV (2012) Spectral inverse quantum (Spectral-IQ) method for modeling mesoporous systems. Application on silica films by FTIR. Int J Mol Sci 13(12):15925–15941
Putz AM, Putz MV (2013) Spectral-Structure activity relationship (Spectral-SAR) assessment of ionic liquids’ in silico ecotoxicity. In: Kadokawa J (Ed) Ionic liquids—new aspects for the future. InTech, Rijeka, pp 85–126. doi:10.5772/51657; Chapter 4.
Putz MV, Lacrămă A-M, Ostafe V (2007) Spectral-SAR, ecotoxicology of ionic liquids the daphnia magna case. Int J Ecol (former Research Letters in Ecology) 12813:5. doi:10.1155/2007/12813
Putz MV, Putz A-M, Ostafe V, Chiriac A (2010) Spectral-SAR ecotoxicology of ionic liquids-Acetylcholine interaction on E. Electricus Species. Int J Chem Model 2:85–96
Rahman MBA, Jumbri K, Basri M, Abdulmalek E, Sirat K, Salleh AB (2010) Synthesis and physico-chemical properties of new tetraethylammonium-based amino acid chiral ionic liquids. Molecules 15: 2388–2397
Raman CV, Krishnan KS (1928) The optical analog of the Compton effect. Nature 121:711
Raman CV, Krishnan KS (1929) The production of new radiations by light scattering. Proc Roy Soc 122:23
Ranke J, Molter K, Stock F, BottinWeber U, Poczobutt J, Hoffmann J, Ondruschka B, Filser J, Jastorff B (2004) Ecotoxicol Environ Saf 58:396–404
Ranke J, Muller A, Bottin-Weber U, Stock F, Stolte S, Arning J, Stormann R, Jastorff B (2007a) Lipophilicity parameters for ionic liquid cations and their correlation to in vitro cytotoxicity. Ecotoxicol Environ Saf 67:430–438
Ranke J, Stolte S, Stormann R, Arning J, Jastorff B (2007b) Chem Rev 107:2183–2206
Ranke J, Othman A, Fan P, Müller A (2009) Explaining ionic liquid water solubility in terms of cation and anion hydrophobicity. Int J Mol Sci 10(3):1271–1289
Romero A, Santos A, Tojo J, Rodriguez A (2008) J Hazard Mater 151:268–273
Scammells PJ, Scott JL, Singer RD (2005) Ionic liquids: the neglected issues. Aust J Chem 58(3):155–169
Seddon KR, Stark A, Torres M-J (2000) Influence of chloride, water, and organic solvents on the physical properties of ionic liquids. Pure Appl Chem 72(12):2275–2287
Smekal A (1923) The quantum theory of dispersion. Naturwissenschaften 11:873
Stark A, Seddon KR (2007) In: Seidel A (Ed) Kirk-Othmer Encyclopaedia of chemical technology, vol 26. Wiley, New York; pp 836–920
Stasiewicz M, Mulkiewicz E, Tomczak-Wandzel R, Kumirska J, Siedlecka EM, Goebiowski M, Gajdus J, Czerwicka M, Stepnowski P (2008) Assessing toxicity and biodegradation of novel, environmentally benign ionic liquids (1-alkoxymethyl-3-hydroxypyridinium chloride, saccharinate and acesulfamates) on cellular and molecular level. Ecotoxicol Environ Saf 71:157–165
Stepnowski P, Skladanowski AC, Ludwiczak A, Laczynska E (2004) Hum Exp Toxicol 23:513–517
Stolte S, Arning J, Bottin-Weber U, Mueller A, Pitner W.R, Welz-Biermann U, Jastorff B, Ranke J (2007a) Green Chem 9:760–767
Stolte S, Matzke M, Arning J, Boschen A, Pitner W.R, Welz-Biermann U, Jastorff B, Ranke J (2007b) Green Chem 9:1170–1179
Stolte S, Abdulkarim S, Arning J, Blomeyer-Nienstedt A-K, Bottin-Weber U, Matzke M, Ranke J, Jastorff B, Thoming J (2008) Primary biodegradation of ionic liquid cations, identification of degradation products of 1-methyl-3-octylimidazoliumchloride and electrochemical wastewater treatment of poorly biodegradable compounds. Green Chem 10:214–224
Suarez PAZ, Selbach VM, Dullius JEL, Einloft S, Piatnicki CMS, Azambuja DS, de Souza RF, Dupont J (1997) Enlarged electrochemical window in dialkyl-imidazolium cation based room-temperature air and water-stable molten salts. Electrochim Acta 42(16):2533–2535
Sutton M (2009) Twinkle, twinkle little star—History of spectroscopy. Chem World 6(12):50–53
Thomas NC (1991) The early history of spectroscopy. J Chem Educ 68(8):631–634
Torrecilla JS, Garcia J, Rojo E, Rodriguez F (2009) Estimation of toxicity of Ionic liquids in Leukemia Rat Cell Line and Acetylcholinesterase enzyme by principal component analysis, neural networks and multiple lineal regressions. J Hazard Mater 164(1):182–194
Torrecilla JS, Palomar J, Lemus J, Rodriguez F (2010) Green Chem 12:123–134
Walden P (1914) Molecular weights and electrical conductivity of several fused salts Bull. Acad Imper Sci (St. Petersburg) 8:405–422
Wei D, Ivaska A (2008) Applications of ionic liquids in electrochemical sensors Analytica Chimica Acta 607(2):126–135
Wilkes JS, Zaworotko MJ (1992) Air and water stable 1-Ethyl-3-Methylimidazolium based ionic liquids. J Chem Soc Chem Comm 1992:965–967
Yang X, Chen QY, Li X, Gao J (2012) Functional ionic liquids induced the formation of mitochondria targeted fluorescent core-shell ellipsoidal nanoparticles with anticancer properties. Coll Surf B Biointerfaces 98:91–96
Yoshida Y, Baba O, Saito G (2007) Ionic liquids based on dicyanamide anion: influence of structural variations in cationic structures on ionic conductivity. J Phys Chem B 111(18):4742–4749
Yu YH, Lu XM, Zhou Q, Dong K, Yao HW, Zhang SJ (2008) Chem Eur J 14:11174–11182
Zhang Q, Li Z, Zhang J, Zhang S, Zhu L, Yang J, Zhang X, Deng Y (2007) Physicochemical properties of nitrile-functionalized ionic liquids. J Phys Chem B 111:2864–2872
Zhang S, Lu X, Zhang Y, Zhou Q, Sun J, Han L, Yue G, Liu X, Cheng W, Li S (2009) Ionic liquids and relative process design molecular thermodynamics of complex systems. Struct Bond 131:143–191
Zhao D, Fei Z, Ang WH, Dyson PJ (2007) Sulfonium-based Ionic liquids incorporating the allyl functionality. Int J Mol Sci 8:304–315
Acknowledgement
Authors thank West University of Timişoara; Faculty of Chemistry, Biology, Geography; and Biology-Chemistry Department, for working and research facilities provided for the present joint chapter though the recent accredited “Laboratory of Computational and Structural Physical-Chemistry for Nanosciences and QSAR”. AMP kindly thanks Romanian Academy too.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2015 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Putz, M., Dudaş, N., Putz, AM. (2015). Bondonic Chemistry: Predicting Ionic Liquids’ (IL) Bondons by Raman-IR Spectra. In: Putz, M., Ori, O. (eds) Exotic Properties of Carbon Nanomatter. Carbon Materials: Chemistry and Physics, vol 8. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-9567-8_13
Download citation
DOI: https://doi.org/10.1007/978-94-017-9567-8_13
Published:
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-017-9566-1
Online ISBN: 978-94-017-9567-8
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)