МОЛЕКУЛЯРНІ КОМПЛЕКСИ ОКСИДУ СІРКИ(IV) З N,O-ВМІСНИМИ ОРГАНІЧНИМИ ОСНОВАМИ (ОГЛЯД)

Автор(и)

  • R. E. Khoma Одеський національний університет імені І. І. Мечникова; Фізико-хімічний інститут захисту навколишнього середовища і людини, Україна
  • A. A. Ennan Фізико-хімічний інститут захисту навколишнього середовища і людини, Україна

DOI:

https://doi.org/10.18524/2304-0947.2016.3(59).79510

Ключові слова:

оксид сірки (IV), N, O-вмісні органічні основи, комплекси з переносом заряду, ван-дер-ваальсові комплекси

Анотація

Систематизовано та узагальнено літературні дані щодо синтезу, стехіометрії, будови  та відносної стійкості молекулярних комплексів оксиду сірки (IV) з N,O-вмісними органічними основами. Особливу увагу приділено механізмам утворення комплексів з переносом заряду, в яких реалізується S←N и S←O зв'язування, а також ван-дер-ваальсових комплексів. Відзначено кореляції між електронними, спектральними параметрами, будовою, відносною стійкістю і іншими характеристиками утворених сполук.

Посилання

Wang X.-B., Du J.-B., Cui H. Sulfur dioxide, a double-faced molecule in mammals. Life Sci., 2014, vol. 98, no 2, pp. 63-67. http://dx.doi.org/10.1016/j.lfs.2013.12.027

Shallcross D.E. Dirty air.Educ. Chem., 2006, vol. 43, no5, pp. 131-135.

Gelmboldt V.O., Khoma R.E., Ennan A.A. Organic bases in the processes of catching and utilization of sulfur oxide (IV) (review). Jenergotehnologii i resursosberezhenie, 2008, no 4, pp. 51–58. (in Russian)

Huang K., Lu J.-F., Wu Y.-T., Hu X.-B., Zhang Z.-B. Absorption of SO2in aqueous solutions of mixed hy-droxylammonium dicarboxylate ionic liquids. Chem. Eng. J., 2013, vol. 215–216, pp. 36–44. http://dx.doi.org/10.1016/j.cej.2012.10.091

Hong S.Y., Kim H., Kim Y.J., Jeong J., Cheong M., Lee H., Kim H.S., Lee J.S. Nitrile-functionalized tertiary amines as highly efficient and reversible SO2absorbents. J. Hazard. Mater., 2014, vol. 264, pp. 136–143. http://dx.doi.org/10.1016/j.jhazmat.2013.11.026

Ennan A.A., Kats B.M. Silicon Tetrafluoride Adducts. Russ. Chem. Rev., 1974, vol. 43, no 7, pp. 539–550. http://dx.doi.org/10.1070/RC1974v043n07ABEH001830

Ennan А.А., Gelmboldt V.O., Gavrilova L.А. Stereohimija i reakcionnaja sposobnost’ ftorokompleksov kremnija. Мoscow, VINITI, 1989, 100 p. (in Russian)

Ennan А.А., Gelmboldt V.O. Tetraftorid kremnija v reakcijah s organicheskimi osnovanijami. Odessa, Ecology, 2005, 160 p. (in Russian)

Gelmboldt V.O. «Onium» fluorosilicates: structures, properties, practical applications. Odessa, Astroprint, 2012, 160 p. (in Russian)

Young N.A. Main Group Coordination Chemistry at Low Temperatures: A Review of Matrix Isolated Group 12 to Group 18 Complexes. Coord. Chem. Rev., 2013, vol. 257, no 5-6, pp. 956−1010. http://dx.doi.org/10.1016/j.ccr.2012.10.013

Mews R., Lork E., Watson P.G., Gortler B. Coordination chemistry in and of sulfur dioxide.Coord. Chem. Rev., 2000, vol. 197, pp. 277-320. http://dx.doi.org/10.1016/S0010-8545(99)00191-5

Emmett E.J., Willis M.C. The development and application of sulfur dioxide surrogates in synthetic organic chemistry. Asian J. Org. Chem., 2015, vol. 4, no 7, pp. 602-611. http://dx.doi.org/10.1002/ajoc.201500103

Nikitin V.I. On interaction of nitrogen-containing organic bases with sulfur dioxide. Vіsn. Odes. nac. unіv., Hіm., 2003, vol. 8, no 4, pp. 200-211. (in Russian)

Khoma R.E., Nikitin V.I., Sokhranenko G.P., Gavrilenko M.I. SO2 acid-base interaction with aqueous solutions of nitrogen-containing compounds (review). Vіsn. Odes. nac. unіv., Hіm., 2002, vol. 6, no 8, pp. 176-193. (in Ukrainian)

Bae S.C., Son H.S., Kim G.H., Ku J.K. Vibronic Relaxation among the Clements Bands of SO2from the E-Band Excitation. J. Phys. Chem. A., 1999, vol. 1-3, pp. 7432-7436. http://dx.doi.org/10.1021/jp990390f

Guantes R., Farantos S.C. High order finite difference methods algorithms far solving Scrodinger equation in molecular dynamics. II Periodic variables. J. Chem. Phys., 2000, vol. 113, no 23, pp. 10429–10437. http://dx.doi.org/10.1063/1.1324004

Prosmiti R., Farantos S.C., Guo H. Assigning the transition from normal to local vibrotional mode in SO2 by periodic orbits. Chem. Phys. Lett., 2000, no 311, pp. 241–247. http://dx.doi.org/10.1016/s0009-2614(99)00850-7

Cooper G., Zarate E.B., Jones R.K., Brion C.E. Absolute oscillator strengths for photoabsorption, photoioniza-tion and ionic photofragmentation of sulphur dioxide. I. The valence shell. Chem. Phys., 1991, vol. 150, no 2, pp. 237-250. http://dx.doi.org/10.1016/0301-0104(91)80132-2

Singh P.J., Shastri A., D’Souza R., Bhaskara Rao S.V.N., Jagatap B.N. VUV photoabsorption spectroscopy of sulphur dioxide in the 1400-1600 Å region: Vibronic analysis of the E~X~system J. Quant. Spectrosc. Radiat. Transfer., 2012, vol. 113, no 4, pp. 267-278. http://dx.doi.org/10.1016/j.jqsrt.2011.11.007

Gillespie R.J., Hargittai I. The VSEPR Model of Molecular Geometry. Boston, Allyn&Bacon, 2012, 260 p.

Khoma R.E., Gavrilenko M.I., Nikitin V.I. Semiempirical Researches of Interaction of Sulfur Dioxide with Urea in Water by Monte-Carlo Method. Vіsn. Odes. nac. unіv., Hіm., 2004, vol. 9, no 2, pp. 28-45. (in Ukranian)

Li S., Kurtz H., Korambath P., Li Y.-S. Infrared spectra, photochemistry, and ab initio calculations of matrix isolated methanethiol/sulfur dioxide complex. J. Mol. Struct., 2000, vol. 550-551, pp. 235–244. http://dx.doi.org/10.1016/S0022-2860(00)00520-2

Risberg E.D., Eriksson L., Mink J., Pettersson L.G.M., Skripkin M.Yu., Sandström M. Sulfur X-ray Absorp-tion and Vibrational Spectroscopic Study of Sulfur Dioxide, Sulfite, and Sulfonate Solutions and of the Substi-tuted Sulfonate Ions X3CSO3-(X = H, Cl, F). Inorg. Chem., 2007, vol. 46, no 20, pp. 8332–8348. http://dx.doi.org/10.1021/ic062440i

Magnusson E. Hypercoordinate molecules of second-row elements: d functions or d orbitals?J. Am. Chem. Soc., 1990, vol. 112, no 22, pp. 7940–7951. http://dx.doi.org/10.1021/ja00178a014

Schenk W.A. Sulfur Oxides as Ligands in Coordination Compounds. Angew. Chem. Int. Edn. Engl. 1987, vol. 26, pp. 98-109. http://dx.doi.org/10.1002/chin.198724352

Pearson R.G. Hard and soft acids and bases – the evolution of a chemical concept. Coord. Chem. Rev., 1990, vol. 100, pp. 403-425. http://dx.doi.org/10.1016/0010-8545(90)85016-L

Larson J.W., McMahon T.B. Fluoride and chloride affinities of main group oxides, fluorides, oxofluorides, and alkyls. Quantitative scales of Lewis acidities from ion cyclotron resonance halide-exchange equilibria. J. Am. Chem. Soc., 1985, vol. 107, no 4, pp. 766-773. http://dx.doi.org/10.1002/chin.198527075

Brinkmann N.R., Tschumper G.S., Schaefer III H.F. Electron affinities of the oxides of aluminum, silicon, phosphorus, sulfur, and chlorine. J. Chem. Phys., 1999, vol. 110, no 13, pp. 6240-6245. http://dx.doi.org/10.1063/1.478528

Laurence C., Gal J.-F. Lewis Basicity and Affinity Scales: Data and Measurement. John Wiley & Sons Ltd, 2010, 476 p. http://dx.doi.org/10.1002/9780470681909

Vogel G.C., Drago R.S. The ECW Model. J. Chem. Educ., 1996, vol. 73, no 8, pp. 701-707. http://dx.doi.org/10.1021/ed073p701

Adams W.A., Kruus P., Patraboy T.J. The system sulfur dioxide – N-methyl-2-pyrrolidinone. Can. J. Chem./Rev. Can. Chim., 1983, vol. 61, no 1, pp. 37-44. http://dx.doi.org/10.1139/v83-007

Hartel G.H. Low-Volatility Polar Organic Solvents for Sulfur Dioxide, Hydrogen Sulfide, and Carbonyl Sulfide. J. Chem. Eng. Data., 1985, vol. 30, no 1, pp. 57–61. http://dx.doi.org/10.1021/je00039a019

Gill J.B., Goodall D.C., Jeffreys B., Gans P. Reactions in mixed non-aqueous solutions containing sulphur diox-ide. Part 7. A Raman spectroscopic study of adduct formation between sulphur dioxide and dimethyl sulphoxide. J. Chem. Soc., Dalton Trans., 1986, no 12, pp. 2597–2602. http://dx.doi.org/10.1039/dt9860002597

Gill J.B., Goodall D.C., Jeffreys B. Reactions in mixed non-aqueous solutions containing sulphur dioxide. Part 8. Phase studies of sulphur dioxide–dimethyl sulphoxide and sulphur dioxide–dimethylformamide mixtures. J. Chem. Soc., Dalton Trans., 1986, no 12, pp. 2603–2605. http://dx.doi.org/10.1039/dt9860002603

Faria D.L.A., SantosP.S. 13C NMR Spectra of some Sulphur Dioxide-Aromatic Amine Complexes. Magn. Reson. Chem., 1987, vol. 25, no 7, pp. 592–593. http://dx.doi.org/10.1002/mrc.1260250708

Demyanovich R.J., Lynn S. Vapor-Liquid Equilibria of Sulfur Dioxide in Polar Organic Solvents. Ind. Eng. Chem. Res., 1987, vol. 26, no 3, pp. 548–555. http://dx.doi.org/10.1021/ie00063a022

Sciamanna S.F., Lynn S. Solubility of Hydrogen Sulfide, Sulfur dioxide, Carbon Dioxide, and n-Butane in Poly(glycol ethers). Ind. Eng. Chem. Res., 1988, vol. 27, pp. 492-499.

Dam M.H.H., Lamine A.S., Roizard D., Lochon P., Roizard C. Selective Sulfur Dioxide Removal using Organic solvents. Ind. Eng. Chem Res., 1997, vol. 36, no 11, pp. 4628–4637. http://dx.doi.org/10.1021/ie970111f

Kermadec R., Lapoicque F., Roizard D., Roizard C. Characterization of the SO2-N-Formylmorpholine Com-plex: Application to a Regenerative Process for Waste Gas Scrubbing. Ind. Eng. Chem. Res., 2002, vol. 41, no 2, pp. 153-163. http://dx.doi.org/10.1021/ie010173c

Nagel D., Kermadec R., Lintz H.G, Roizard C., Lapoicque F. Absorption of sulfur dioxide in N-formylmorpho-line: investigations of the kinetics of the liquid phase reaction. Chem. Eng. Sci., 2002, vol. 57, no 22-23, pp. 4883-4893. http://dx.doi.org/10.1016/s0009-2509(02)00283-x

Heldebrant D.J., Yonker C.R., Jessop P.G., Phan L. Reversible Uptake of COS, CS2, and SO2: Ionic Liquids with OAlkylxanthate, O-Alkylthiocarbonyl, and O-Alkylsulfite Anions. Chem. Eur. J., 2009, vol. 15, no 31, pp. 7619-7627. http://dx.doi.org/10.1002/chem.200802602.

Heldebrant D.J., Koech P.K., Yonker C.R. A reversible zwitterionic SO2-binding organic liquid. Energy Envi-ron. Sci., 2010, vol. 3, no 1, pp. 111-113. http://dx.doi.org/10.1039/B916550A

Ando R.A., Matazo D.R.C., Santos P.S. Detailed analysis of the charge transfer complex N,N-dimethylaniline–SO2 by Raman spectroscopy and density functional theory calculations. J. Raman Spectrosc., 2010, vol. 41, no 7, pp. 771–775. http://dx.doi.org/10.1002/jrs.2514

Nagai T., Katayama K., Tokura N. Electron transfer from amines to liquid sulfur dioxide. Chem. Lett., 1973, vol. 2, no 8, pp. 919-922. http://doi.org/10.1246/cl.1973.919

Wu K.T., Yencha A.J. Rate processes and nuclear magnetic resonance spectra of amine•SO2complexes + H2O in liquid SO2. Can. J. Chem., 1981, vol. 59, no 1, pp. 8-13. http://dx.doi.org/10.1139/v81-002

Ramadan A.M. Sintez i fiziko-himicheskie issledovanija produktov vzaimodejstvija oksida sery (IV) s aro-maticheskimi i geterociklicheskimi azotsoderzhashhimi osnovanijami. Diss. Candidate of Chemical Sciences, Odessa, 1994, 121 p.

Kurando S.V. Koordinacionnye soedinenija oksidov sery (IV) i (VI) s azotsoderzhashhimi organicheskimi os-novanijami. Diss. Candidate of Chemical Sciences, Odessa, 1995, 130 p.

Kurando S.V., Nikitin V.I. The adducts of sulfur dioxide with alkylamines. Vіsn. Odes. nac. unіv., Hіm., 2002, vol. 6, no 7, pp. 94–99.

Ennan А.А., Nikitin V.I., Gudimovich T.F., Berezina L.P., Tikhonenko L.M. Kompleksoobrazovanie oksida sery (IV) s p, o-toluidinom. Zhurn. neorgan. himii., 1989, vol. 34, no 3, pp. 783–786. (in Russian)

Mokhamed R.A., Nikitin V.I., Karpinchik V.A. Issledovanie vzaimodejstvija oksida sery (IV) s piridinom i izomernymi pikolinami. Zhurn. neorgan. himii., 1993, vol. 38, no 4, pp. 621–624. (in Russian)

Nikitin V.I., Sokhranenko G.P., Karpinchik V.A., Mokhamed R.A. Kompleksoobrazovanie ok-sida sery (IV) c 4,4’-dipiridilom. Izv. VUZov. Khimija i khim. tehnol., 1994, vol. 37, no 1, pp. 30–34. (in Russian)

Berezіna L.P., Nіkіtіn V.І., Sokhranenko G.P., Samojlenko G.V. Vpliv etilenglіkolju і sorbіtu na fіziko-hіmіchnі vlastivostі etanolamіnіv. Vіsn. Odes. nac. unіv., Hіm., 2000, vol. 5, no 2, pp. 3–8. (in Russian)

Nіkіtіn V.І., Khoma R.Е, Gavrilenko M.I. Potentiometric studies on sulfur dioxide sorption by aqueous carb-amide solution. Izv. VUZov. Khimija i khim. tehnol., 2000, vol. 43, no 2, pp. 14–16. (in Russian)

Khoma R.Е, Nіkіtіn V.І., Gavrilenko M.I. pH-metric investigation of sulfur dioxide sorption by 0.1 M urea solu-tion. Izv. VUZov. Khimija i khim. tehnol., 2001, vol. 44, no 6, pp. 42–44. (in Russian)

Kurando S.V., Nikitin V.I. Synthesis and physico-chemical studies on the products of the interaction of sulfur dioxide with benzylamines. Vіsn. Odes. nac. unіv., Hіm., 2002, vol. 6, no 6, pp. 164–168. (in Ukranian)

Khoma R.E., Nikitin V.I., Gavrilenko M.I. On reaction of sulfur dioxide with aqueous solutions of carbamide. Russ. J. Appl. Chem., 2003, vol. 76, no 4, pp. 513-517.

Khoma R.E., Gavrilenko M.I., Nikitin V.I. A study of complexation in the system constituted by water, carb-amide, and sulfur dioxide at 293 K. Russ. J. Appl. Chem., 2004, vol. 77, no 8, pp. 1249-1254.

Khoma R.E., Gavrilenko M.I., Nikitin V.I. Interaction of Sulfur Dioxide with Aqueous Solutions of Amides. Russ. J. Gen. Chem., 2005, vol. 75, no 5, pp. 727-733. http://dx.doi.org/10.1007/s11176-005-0308-9.

Dehghani H., Fathi F. Molecular complexation of meso-tetraphenylporphyrins with SO2. Dyes Pigments., 2008, vol. 77, no 2, pp. 323–326. http://dx.doi.org/10.1016/j.dyepig.2007.05.017

Basu R.K., Dutta B.K. Kinetics of absorption of sulfur dioxide in dimethylaniline solution. Can. J. Chem. Eng., 1987, vol. 65, no 1, pp. 27-35. http://dx.doi.org/10.1002/cjce.5450650106

Wong M.W., Wiberg K.B. Srtuctures, Bonding, and Absorption Spectra of Amine – Sulfur Dioxide Charge-Transfer Complexes. J. Am. Chem. Soc., 1992, vol. 114, pp. 7527-7535. http://dx.doi.org/10.1021/ja00045a028

Eigner A.A., Wrass J.P., Smith E.L., Knutson C.C., Phillips J.A. Structural properties of CH3CN-SO2 in the gas phase and condensed-phase media via density functional theory and infrared spectroscopy. J. Mol. Struct., 2009, vol. 919, no 1-3, pp. 312-320. http://dx.doi.org/10.1016/j.molstruc.2008.09.024

Ito F., Hirabayashi S. Infrared spectroscopy of SO2clusters in rare gas matrices revisited: Assignment of species in Ar matrix. Chem. Phys., 2009, vol. 358, no 3, pp. 209–218. http://dx.doi.org/10.1016/j.chemphys.2009.02.007

Phillips J.A., Britton D., Leopold K.R. Gas-solid structure differences in the donor-acceptor complex (CH3)2HN−SO2. J. Chem. Crystallogr., 1996, vol. 26, no 8, pp. 533-538. http://dx.doi.org/10.1007/BF01668411

LaBarge M.S., Matos J., Hillig K.W., Kuczkowski R.L. Microwave Spectrum and Structure of the Trimethyl-amine – Sulfur Dioxide Charge –Transfer Complex. J. Am. Chem. Soc., 1987, vol. 109, pp. 7222-7223. http://dx.doi.org/10.1021/ja00257a070

Labarge M.S., Oh J.-J., Hillig II K.W., Kuczkowski R.L. The benzene-SO2and pyridine-SO2complexes. Chem. Phys. Lett., 1989, vol. 159, no 5–6, pp. 559-562. http://dx.doi.org/10.1016/0009-2614(89)87532-3

Oh J.J., HilligII K.W., Kuczkowski R.L. Microwave spectrum and structure of the pyridine-sulfur dioxide com-plex. J. Am. Chem. Soc., 1991, vol. 113, no 20, pp. 7480–7484. http://dx.doi.org/10.1021/ja00020a004

Oh J.J., HilligII K.W., Kuczkowski R.L. Structure of the Dimethylamine-Sulfur Dioxide Complex. J. Phys. Chem., 1991, vol. 95, no 19, pp. 7211-7216. http://dx.doi.org/10.1021/j100172a022

Structure and Dynamics of Solutions.Ed. H. Ohtaki,H. Yamatera. Stud. Phys. Theor. Chem., 1992, vol. 79, pp. 16. http://dx.doi.org/10.1016/c2009-0-10162-9

Chemical Processes with Participation of Biological and Related Compounds.Biophysical and Chemical As-pects of Porphyrins, Pigments, Drugs, Biodegradable Polymers and Nanofibers. Ed. T.N. Lomova, G.E. Zaikov. Leiden-Boston, Netherland, Brill, 2008, pp. 194.

Nikitin V.I., Karpinchik V.A., Mokhamed R.A., Gelmboldt V.O. Synthesis, IR spectra, and thermochemi-cal properties of sulfur(IV) oxide adducts with arylamines. Zhurn. Neorgan. Khim., 1996, vol. 41, no 2, pp. 283–286. (in Russian)

Sohranenko G.P., Nikitin V.I., Karpinchik V.A., Mohamed Ramadan Issledovanie processov vzaimodejst-vija oksida sery (IV) s aromaticheskimi aminami. Izv. VUZov. Khimija i khim. tehnol., 1994, vol. 37, no 2, pp. 20-24. (in Russian)

Pradeep T., Sreekanth C.S., Hegde M.S., Rao C.N.R. Experimental electronic structures of sulfur dioxide com-plexes: an electron spectroscopic study. J. Am. Chem. Soc., 1989, vol. 111, no 14, pp. 5058–5063. http://dx.doi.org/10.1021/ja00196a006

Kanamueller J.M. Sulfur dioxide adducts of some disubstituted hydrazines. J. Inorg. Nucl. Chem., 1971, vol. 33, no 12, pp. 4051-4055. http://dx.doi.org/10.1016/0022-1902(71)80503-1

Keller J.W. Sulfur Dioxide−Pyridine Dimer. FTIR and Theoretical Evidence for a Low-Symmetry Structure. J. Phys. Chem. A., 2015, vol. 119, no 41, pp. 10390–10398. http://dx.doi.org/10.1021/acs.jpca.5b06122

Maier N., Schiewe J., Matschiner H., Maschmeier C.-P., Boese R. Zur Struktur Von Sek. Amin-SO2-komplexen. Phosphorus Sulfur., 1994, vol. 91, no 1-4, pp. 179-188. http://dx.doi.org/10.1080/10426509408021944

Shannon M.S., Irvin A.C., Liu H., Moon J.D., Hindman M.S., Turner C.H., Bara J.E. Chemical and Physical Absorption of SO2

by N-Functionalized Imidazoles: Experimental Results and Molecular-level Insight. Ind. Eng. Chem. Res., 2015, vol. 54, no 1, pp. 462–471. http://dx.doi.org/10.1021/ie503752h

Sohranenko G.P., Nikitin V. I., Karpinchik V.A., Berezina L.P. O vzaimodejstvii v treh-komponentnyh sistemah SO2– p-anizidin – C2H5OH i SO2–5,6-benzohinolin–C2H5OH pri 200C. Izv. VUZov. Khimija i khim. tehnol., 1999, vol. 42, no 6, pp. 33–36. (in Russian)

Steudel R., Steudel Y. Charge-Transfer Complexes between the Sulfur Molecules SO2, S2O, S3, SONH, and SOCl2 and the Amine Donors NH3and NMe3– A Theoretical Study. Eur. J. Inorg. Chem., 2007, vol. 2007, no 27, pp. 4385–4392. http://dx.doi.org/10.1002/ejic.200700399

Sohranenko G.P., Berezina L.P., Karpinchik V.A., Nikitin V.I. Kompleksoobrazovanie oksida sery (IV) s geksa-metilendiaminom. Zhurn. Neorgan. Khim., 1992, vol. 37, no 10, pp. 2265-2268. (in Russian)

Martial L., Bischoff L. Stoichiometric Release of SO2 from Adducts: Application to the Direct Synthesis of Protected Dienes Source. Synlett., 2015, vol. 26, no 9, pp. 1225-1229. http://dx.doi.org/10.1055/s-0034-1380508

Childs J.D., Helm D.V., Christian S.D. Amine-sulfur dioxide complexes. Structure of N,N,N’,N’-tetrameth-yl-p-phenylenediamine-bis(sulfur dioxide). Inorg. Chem., 1975, vol. 14, no 6, pp. 1386–1390. http://dx.doi.org/10.1021/ic50148a036

Woolven H., González-Rodríguez C., Marco I., Thompson A.L., Willis M.C. DABCO-Bis(sulfur dioxide), DABSO, as a Convenient Source of Sulfur Dioxide for Organic Synthesis: Utility in Sulfonamide and Sulfamide Preparation. Org. Lett., 2011, vol. 13, no 18, pp. 4876-4878. http://dx.doi.org/10.1021/ol201957n

Huang K., Xia S., Zhang X.-M., Chen Y.-L., Wu Y.-T., Hu X.-B. Comparative Study of the Solubilities of SO2 in Five Low Volatile Organic Solvents (Sulfolane, Ethylene Glycol, Propylene Carbonate, N-Methylimidazole, and N-Methylpyrrolidone). J. Chem. Eng. Data., 2014, vol. 59, no 4, pp. 1202-1212. http://dx.doi.org/10.1021/je4007713

Sokhranenko G.P., Gavrilenko M.I. Generalization of the Results of Studies in Ternary Systems SO2– Am – Sol-vent. Vіsn. Odes. nac. unіv., Hіm., 2006, vol. 11, no 1, pp. 26-34. (in Russian)

Khoma R.E. Acid-base interaction of sulfur dioxide with amides aqueous solutions: thesis for the degree of Candidate of Chemical Sciences, Odessa, 2005, 21 p.

Khoma R.E., Gelmboldt V.О., Ennan А.А., Baumer V.N., Tsapko M.D.Interaction Products in the System Sulfur Dioxide – 2,2’-Bipyridine – Water. Van der Waals Clathrates. Russ. J. Gener. Chem., 2016, vol. 86, no 8, pp. 2237-2241. http://dx.doi.org/10.1134/S1070363216090097

Khoma R.Е., Shestaka А.А., Gelmboldt V.О. The interaction of sulphur dioxide with 2-imidazolidinone and biuret in aqueous solutions. Vіsn. Odes. nac. unіv., Hіm., 2009, vol.14, no 11, pp. 62-70. (in Russian)

Khoma R.Е. The composition and the relative stability of complexation products in «sulphur dioxide – amide – water» systems. Vіsn. Odes. nac. unіv., Hіm., 2012, vol. 17, no 2, pp. 49-57. http://dx.doi.org/10.18524/2304-0947.2012.2(42).31998 (in Russian)

Santos P.S., Lieder R. On the interaction of hexamethylenetetramine and sulfur dioxide // J. Mol. Struct. – 1986. – Vol. 144, No 1–2. – P. 39-45. http://dx.doi.org/10.1016/0022-2860(86)80165-X

Khoma R.Е., Shestaka А.А., Koroeva L.V., Ennan Gelmboldt V.О. Process for the preparation of aminometh-anesulfonic acid. Patent UA, no 59830, 2011. (in Ukrainian)

Khoma R.E., Shestaka A.A., Shishkin O.V., Baumer V.N., Brusilovskii Yu.E., Koroeva L.V., Ennan A.A., Gelm-bold V.O. Features of interaction in the sulfur(IV) oxide-hexamethylenetetramine-water system: A first example of identification of the product with a sulfur-carbon bond. Rus. J. Gen. Chem. – 2011. – Vol. 81, No 3. – P. 620-621. http://dx.doi.org/10.1134/S1070363211030352

Berezina L.P., Nikitin V.I., Sohranenko G.P. Vyznachennja skladu i stijkosti kompleksiv oksydu sirky (IV) z etanolaminamy v nevodnyh i vodnyh seredovyshhah. Vіsn. Odes. nac. unіv., Prirodnichі nauki, 1998, no 2, pp. 16–18. (in Ukrainian)

Kogtev S.E., Blokhin P.V., Ksandrov N.V., Borisenko A.S. Recovery of sulfur dioxide from discharged gases using amine-containing sorbents. Russ. J. Appl. Chem., 1999, vol. 72, no 10, pp. 1777-1779.

Blokhin P.V., Kogtev S.E., Petrov A.V., Oblivina T.A. Treatment of exhaust gases with methyldiethanolamine solution to remove sulfur dioxide. Russ. J. Appl. Chem., 2000, vol. 73, no 8, pp. 1417-1419.

Yang D., Hou M., Ning H., Zhang J., Ma J., Han B. Efficient SO2capture by amine functionalized PEG. Phys. Chem. Chem. Phys., 2013, vol. 15, no 41, pp. 18123-18127. http://dx.doi.org/10.1039/C3CP52911H

Tailor R., Sayari A. Grafted propyldiethanolamine for selective removal of SO2in the presence of CO2. Chem. Eng. J., 2016, vol. 289, pp. 142-149. http://dx.doi.org/10.1016/j.cej.2015.12.084

Ford T.A. Ab initio molecular orbital calculations of the structures and vibrational spectra of some molec-ular complexes containing sulphur dioxide. J. Mol. Struct., 2009, vol. 924–926, pp. 466–472. http://dx.doi.org/10.1016/j.molstruc.2008.10.007

Mingos D.M.P. A theoretical analysis of ambivalent and ambiphilic Lewis acid/bases with symmetry signatures. Coord. Chem. Rev., 2014, vol. 293, pp. 2-18. http://dx.doi.org/10.1016/j.ccr.2014.11.009

Shim J.-G., Jhon Y.-H., Kim J.-H., Jang K.-R., Kim J.-H. Computational Studies on the Sulfur Dioxide Ab-sorption by Organic Lewis Bases. Bull. Korean Chem. Soc., 2007, vol. 28, no 9, pp. 1609-1612. http://dx.doi.org/10.5012/bkcs.2007.28.9.1609

Helm D., Childs J.D., Christian S.D. The geometry of the charge transfer complex (CH3)3N·SO2 in the solid state. J. Chem. Soc. D., 1969, no 15, pp. 887-888. http://dx.doi.org/10.1039/C29690000887.

Oh J.J., LaBarge M.S., Matos J., Kampf J.W., HilligII K.W., Kuczkowski R.L. Structure of the trimethylamine-sulfur dioxide complex.J. Am. Chem. Soc., 1991, vol. 113, no 13, pp. 4732–4738. http://dx.doi.org/10.1021/ja00013a003

Singh U.C., Kollman P.A. Ab initio calculations on the structure and nature of the hydrogen bonded complex H2S···HF. J. Chem. Phys., 1984, vol. 80, pp. 353-355. http://dx.doi.org/10.1063/1.446454

Taleb-Bendiab A., Hillig II K.W., Kuczkowski R.L. Microwave spectrum of benzene·SO2: Barrier to inter-nal rotation, structure, and dipole moment. J. Chem. Phys., 1992, vol. 97, no 5, pp. 2996-3006. http://dx.doi.org/10.1063/1.463041

Toužín J., NeplechováK., Žák Z., Černík M. Syntheses and structures of donor–acceptor complexes of selenium dioxide with pyridine and trimethylamine. Collect. Czech. Chem. Commun., 2002, vol. 67, pp. 577-586.

Smith M.B. March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley, New York, 2013, 2080 p.

Faria D.L.A., Santos P.S. Raman and infrared spectra of some aromatic amine–sulphur dioxide molecular complexes. J. Raman Spectrosc., 1988, vol. 19, no 7, pp. 471–478. http://dx.doi.org/10.1002/jrs.1250190708

Gao F., Zhang J., Niu Y., Wei X. Desorption Property and Spectral Investigation of Dilute Sulfur Dioxide in Ethylene Glycol + N,N-Dimethylformamide System. Ind. Eng. Chem. Res., 2014, vol. 53, no 19, pp. 7871-7876. http://dx.doi.org/10.1021/ie500427m

Batsanov S.S. Van der Waals Radii of Elements. Inorg. Mater., 2001, vol. 37, no 9, pp. 871–885. http://dx.doi.org/10.1023/A:1011625728803

Cordero B., Gómez V., Platero-Prats A.E., Revés M., Echeverría J., Cremades E., Barragán F., Alvarez S. Co-valent radii revisited. Dalton Trans., 2008, vol. 21, pp. 2832–2838. http://dx.doi.org/10.1039/b801115jCor-dero_2008

Leopold K.R., Canagaratna M., Phillips J.A. Partially Bonded Molecules from the Solid State to the Strato-sphere. Acc. Chem. Res., 1997, vol. 30, no 2, pp. 57-64. http://dx.doi.org/10.1021/ar950115l

Fiacco D.L., Toro A., Leopold K.R. Structure, Bonding, and Dipole Moment of (CH3)3N−SO3. A Microwave Study. Inorg. Chem., 2000, vol. 39, no 1, pp. 37–43. http://dx.doi.org/10.1021/ic990925j

Mo Y., Gao J. Polarization and Charge-Transfer Effects in Lewis Acid−Base Complexes. J. Phys. Chem. A., 2001, vol. 105, no 26, pp. 6530–6536. http://dx.doi.org/10.1021/jp010348w

Post B., Schwartz R.S., Fankuchen I. The crystal structure of sulfur dioxide. Acta Cryst., 1952, vol. 5, no 3, pp. 372-374. http://dx.doi.org/10.1107/S0365110X5200109X

Morino Y., Tanimoto M., Saito S. Critical Survey of the Molecular Structure Determination by the Use of Spec-troscopic Data for SO2. Acta. Chem. Scand., 1988, vol. 19, no 46, pp. 346-351. http://dx.doi.org/10.3891/acta.chem.scand.42a-0346

Hunter E.P.L., Lias S.G. Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Apdate. J. Phys. Chem. Ref. Data., 1998, vol. 27, no 3, pp. 413-656. http://dx.doi.org/10.1063/1.556018

Romm I.P., Noskov Yu.G., Malkova A.A.The strength and length of donor-acceptor bonds in molecular complexes. Russ. Chem. Bull., Int. Ed., vol. 56, no 10, pp. 1935-1944. http://dx.doi.org/10.1007/s11172-007-0300-0

Guryanova E.N., Goldstein I.P., Romm I.P. Donor-Acceptor Bond. Wiley, New York, 1975, 366 pp.

Lihtenshtejn G.I. Kompensacionnyj jeffekt.Himicheskaja jenciklopedija. Pod red. Zefirova N.S. T. 2. Moscow, Sovetskaja jenciklopedija, 1990, pp. 868. (in Russian)

Starikov E.B. Norden B. Entropy-enthalpy compensation as a fundamental concept and analysis tool for systematical experimental data. Chem. Phys. Lett., 2012, vol. 538, pp. 118–120. http://dx.doi.org/10.1016/j.cplett.2012.04.028

Khoma R.E. Thermodynamics of the Dissociation of Aminomethanesulfonic Acid and its N-Substituted Deriva-tives in Aqueous Solutions at 293–313 K. Russ. J. Phys. Chem., 2017, vol. 91, no 1, pp. 76-79. http://dx.doi.org/10.1134/S0036024417010125

Gardner C.L., Day R.W. Vapour pressure and thermodynamic data for the binary liquid mixture of pyridine and sulphur dioxide. Can. J. Chem., 1984, vol. 62, no 5, pp. 986-989. http://dx.doi.org/10.1139/v84-162

Lorimer J.W., Smith B.C., Smith G.H. Total vapour pressures, thermodynamic excess functions and complex formation in binary liquid mixtures of some organic solvents and sulphur dioxide. J. Chem. Soc., Faraday Trans. 1., 1975, vol. 71, pp. 2232-2250. http://dx.doi.org/10.1039/F19757102232

Zipp A.P. Formation thermodynamics of aniline-SO2 adducts. J. Inorg. Nucl. Chem., 1974, vol. 36, no 6, pp. 1399-1402. http://dx.doi.org/10.1016/0022-1902(74)80086-2

Benoit R.L., Milanova E. Vapour pressure and calorimetric data for the solution of sulfur dioxide in aprotic solvents. Can. J. Chem., 1979, vol. 57, no 11, pp. 1319-1323. http://dx.doi.org/10.1139/v79-215

Woods A.S., Ferré S. Amazing Stability of the Arginine−Phosphate Electrostatic Interaction. J. Proteome Res., 2005, vol. 4, no 4, pp. 1397–1402. http://dx.doi.org/10.1021/pr050077s

Grundnes J., Christian S.D. Solvent Effects on Strong Charge-Transfer Complexes. I. Trimethylamine and Sulfur Dioxide in Gas and in Heptane. J. Am. Chem. Soc., 1968, vol. 90, no 9, pp. 2239–2245. http://dx.doi.org/10.1021/ja01011a006

Grundnes J., Christian S.D., Cheam V., Farnham S.B. Solvent Effects on Strong Charge-Transfer Complexes. IV. Trimethylamine and Sulfur Dioxide in the Vapor Phase. J. Am. Chem. Soc., 1971, vol. 93, no 1, pp. 20–23. http://dx.doi.org/10.1021/ja00730a003

Grundnes J., Christian S.D. Solvent Effects on Strong Charge Transfer Complexes. III. Trimethylamine and Sulphur Dioxide in Polar Solvents. Acta Chem. Scand., 1969, vol. 23, no 10, pp. 3583-3585. http://dx.doi.org/10.3891/acta.chem.scand.23-3583

Kuczkowski R.L., Taleb-bendiab A. Tunneling motions in sulfur dioxide complexes. Structures and Conforma-tions of Non-Rigid Molecules., 1993, Vol. 410, pp. 257-276. http://dx.doi.org/10.1007/978-94-011-2074-6_13

Bishop R., Craig D.C., Dance I.G., Scudder M.L., Ung A.T. Interpenetrating inclusion lattices: Comparison of the b-hydroquinone and ellipsoidal clathrate structures. J. Struct. Chem., 1999, vol. 40, no 5, pp. 663–671. http://dx.doi.org/10.1007/BF02903443

Huss А. J., Eckert C.A. Equilibria and ion activities in aqueous sulfur dioxide solutions. J. Phys. Chem., 1977, vol. 81, no 24, pp. 2268–2270. http://dx.doi.org/10.1021/j100539a015

Martell A.E., Smith R.M. Critical stability constants.Vol. 6: Second Supplement. New York, Plenum Press, 1989, 660 p.

Khoma R.E., Gelmboldt V.O., Koroeva L.V., Ennan A.A., Mazepa A.V., Brusilovskiy Yu.E. Spectral characterization of products descriptions of sulphur (IV) oxide ineraction with ethanolamines aqueous solutions.Voprosy khimii i khimicheskoi technologii, 2012, no 1, pp. 133-136. (in Russian)

Khoma R.E., Ennan A.A., Mazepa A.V., Gelmboldt V.O. Spectral characterization of products ineraction of sulphur dioxide with N-alkylated monoethanolamines derivatives aqueous solutions. Voprosy khimii i khimi-cheskoi technologii, 2013, no 1, pp. 136-138. (in Russian)

Khoma R.E., Gelmboldt V.O., Shishkin O.V., Baumer V.N., Puzan A.N., Ennan A.A., Rakipov I.M. Synthesis and structure of N-(hydroxyethyl)ethylenediammonium sulfite monohydrate. Russ. J. Inorg. Chem., 2014, vol. 84, no 5, pp. 541-544. http://dx.doi.org/10.1134/S0036023614060096

Khoma R.E., Gelmboldt V.O., Baumer V.N., Shishkin O.V., Koroeva L.V. Synthesis and structure of aminogua-nidinium sulfite monohydrate. Russ. J. Inorg. Chem., 2013, vol. 58, no 7, pp. 843-847. http://dx.doi.org/10.1134/S0036023613070140

Khoma R.E., Gelmboldt V.O., Shishkin O.V., Baumer V.N., Ennan A.A. Synthesis, crystal structure, vibrational spectra, and thermochemical transformations of tris(hydroxymethyl)aminomethane. Russ. J. Inorg. Chem., 2014, vol. 59, no 1, pp. 1-6. http://dx.doi.org/10.1134/S0036023614010069

Khoma R.E., Ennan A.A., Shishkin O.V., Baumer V.N., Gelmboldt V.O.Products of interaction between Sulfur(IV) oxide and aqueous solutions of hexamethylendiamine and tert-Butylamine: The crystal structure of hexamethylenediammonium sulfate dihydrate. Russ. J. Inorg. Chem., 2012, vol. 57, no 12, pp. 1559-1562. http://dx.doi.org/10.1134/S003602361212008X

Khoma R.E., Gelmboldt V.O., Baumer V.N., Puzan A.N., Ennan A.A. Methylammonium sulfate: Synthe-sis and structure. Russ. J. Inorg. Chem., 2015, vol. 60, no 10, pp. 1199-1203. http://dx.doi.org/10.1134/S0036023615100101

Khoma R.E., Ennan A.A., Gelmboldt V.O., Shishkin O.V., Baumer V.N., Mazepa A.V., Brusilovskii Yu.E. Prep-aration and some physicochemical properties of benzylammonium sulfates. Russ. J. Gen. Chem., 2014, vol. 84, no 4, pp. 637-641. http://dx.doi.org/10.1134/S1070363214040069

Belin C., Roziere J., Potier J. The Structure of 2,2’-Bipyridiniurn Bis(fluorosulfate). Acta Cryst. 1981, vol. B37, pp. 1306-1309. http://dx.doi.org/10.1107/S0567740881005761

Bowen R.J., Fernandes M.A., Gitari P.W., Layh M. 2,2’-Bipyridinium(1+) bromide monohydrateActa Crystal-logr C., 2004, vol. C60(Pt 2), pp. o113-114. http://dx.doi.org/10.1107/S0108270103028282

Ma G., Ilyukhin A., Glaser J. 2,2’-Bipyridinium bis(perchlorate). Acta Crystallogr. C., 2000, vol. C56, pp. 1473-1475. http://dx.doi.org/10.1107/S0108270100012452

##submission.downloads##

Опубліковано

2016-10-11

Як цитувати

Khoma, R. E., & Ennan, A. A. (2016). МОЛЕКУЛЯРНІ КОМПЛЕКСИ ОКСИДУ СІРКИ(IV) З N,O-ВМІСНИМИ ОРГАНІЧНИМИ ОСНОВАМИ (ОГЛЯД). Вісник Одеського національного університету. Хімія, 21(3(59), 6–31. https://doi.org/10.18524/2304-0947.2016.3(59).79510

Номер

Розділ

Статті