Review on synthesis of novel carbonyl derivatives of biological macromolecules by oxidation of polysaccharides with permanganate ion in alkaline media

Refat M. Hassan, S. A. Ibrahim1
1Department of Chemistry, Faculty of Science, New Valley University, El-Kharga, New Valley, 72511, Egypt

Tóm tắt

AbstractSynthesis of mono- and diketones as carbonyl group derivatives in biomacromolecular chemistry is very essential task for industrial biotechnology applications. However, there are various techniques to synthesize such carbonyl groups, the most common and efficient methods are the chemical oxidation of alcoholic biological macromolecule by suitable oxidizing agents. Therefore, diversified oxidants have emerged for such purpose, particularly for the derivatives of polysaccharides as natural polymeric carbohydrates in either acidic or alkaline solutions, however, the permanganate ion was found to be the most competitive oxidizing agent for clean and efficient synthesis of such carbonyl derivatives in alkaline media due to easy removal of formed Mn (IV) by complexation with fluoride ions, giving rise to the insoluble MnF4, which can be separated by filtration. Despite the extensive studies on the oxidation of organic compounds by alkaline permanganate. Little of knowledge regarding the type of electron transfer and transition states involved in the rate-determining processes during the oxidation of alcoholic macromolecules by this oxidant. In addition, the literature survey still remains suffering from a lack of information about the reaction kinetics, mechanistic in terms of the nature of electron-transfer and transition states in the rate determining steps of in such oxidation–reduction systems. All of the above arguments encouraged us to present the current review concerning the synthesis of either mono- or diketo derivatives of such homo (non-sulfated) or hetero (sulfated) polysaccharides using alkaline permanganate, aiming to compensate for the lack of information with respect to the nature of electron transfer pathway routes through pertinent interpretations and discussions, as well as to develop innovative methodologies for the synthesis of carbonyl derivatives of biological macromolecules with high potential applications in pharmaceutics and medicine as well as industrial biotechnology.

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Tài liệu tham khảo

Ali HM, El-Aal MA, Al-Hossainy AF, Ibrahim SM (2022) Kinetics and mechanism studies of oxidation of dibromothymolsulfonphthalein toxic dye by potassium permanganate in neutral media with the synthesis of 2-bromo-6-isopropyl-3-methyl-cyclohexa-2,5-dienone. ACS Omega 7(18):16109–16115

Simandi LI, Jaky M, Schelly ZA (1984) Short-lived manganate (VI) and manganate(V) intermediates in the permanganate oxidation of sulfite ion. J Am Chem Soc 106:6866–6867

Ibrahim SM, Al-Hossainy AF, Saha B, El-Aal MA (2022) Removal of bromothymol blue dye by the oxidation method using KMnO4: Accelerating the oxidation reaction by Ru (III) catalyst. J Mol Str 1268:133679–133686

Fawzi A, El-Guesmi N, Ali HM, Abdalla M (2018) Oxidation of tryptophan by permanganate ion in acid, neutral and alkaline media. A comparative kinetic and mechanistic study. J Mater Environ Sci 9:1645–1655

Andres-Ordax FJ, Arrizabalaga A, Martinez JI (1984) Kinetic-study of the oxidation of L-phenylalanine by potassium-permanganate in neutral medium. An Quim 80:531–535

Jaky M, Simandi L (1976) Mechanism of the permanganate oxidation of unsaturated compounds. Part VI. Kinetic investigation of the oxidation of methylmaleic acid, methylfumaric acid, and dimethylmaleic acid. J Chem Soc Perkin Trans 2:939–943

Banerji KK (1972) The kinetics of the oxidation of acetaldehyde by acid permanganate. Z Naturforsch 27b:772–774

Farkohi SA, Kini AK, Nandibewoor ST (2002) Oxidation of l -hydroxyproline by aqueous alkaline permanganate-A Kinetic study. Inorg React Mech 4:67–76

Kulkarni RM, Bilehal DC, Nandibewoor ST (2002) Kinetic and mechanistic study of oxidation of sulfamethoxazole by alkaline permanganate. Inorg React Mech 3:239–247

Hiremath GC, Kulkarmi RM, Nandibewoor ST (2005) Kinetics of oxidative degradation and deamination of atenolol by aqueous alkaline permanganate. Ind J Chem A 44A:245–250

Jaky M, Trompler ES (2002) Permanganate oxidation of unsaturated alcohols in alkaline media. Inter J Chem Kinet 34:561–567

Bilenhal D, Kulkarni R, Nandibewoor S (2005) Comparative study of the chromium (III) catalyzed oxidation of l-leucine and l-isoleucine by alkaline permanganate: A kinetic and mechanistic approach. J Mol Catal 232:21–28

Ibrahim SM, Saad N, Ahmed MM, El–Aal MA, (2022) Novel synthesis of antibacterial pyrone derivatives using kinetics and mechanism of oxidation of azithromycin by alkaline permanganate. Bioorg Chem 119:105553–105561

Panari RG, Chougale RB, Nandibewoor ST (1998) Kinetics and mechanism of oxidation of L-phenylalanine by alkaline permanganate. Pol J Chem 72:99–107

Mulla RM, Nandibewoor ST (2004) Mechanistic and spectral investigation of the oxidation of 4-hydroxycoumarin by aqueous alkaline permanganate using the stopped flow technique. Polyhedron 23:2507–2513

Jaky M, Szammer, (1997) Oxidation of aldehydes with permanganate in acidic and alkaline media. J Phys Org Chem 10:420–426

Chougale DD, Hiremath GA, Nandibewoor ST (1997) Kinetics and mechanism of oxidation of L-alanine by alkaline permanganate. Pol J Chem 71:1471–1478

Timmanagoudar PL, Hiremath GA, Nandibewoor ST (1997) Permanganate oxidation of chromium(III) in aqueous alkaline medium: a kinetic study by the stopped-flow technique. Trans Met Chem 22:193–196

Ibrahim SM, Al-Hossainy AF, Zoromba MSh, El Azab IH (2021) Base-catalyzed oxidation of sugarcane molasses by potassium ferricyanide in alkaline solutions. Int J Chem Kinet 53:1101–1112

Szammer J, Jaky M, Gerasimov OV (1992) Oxidation by Permanganate in strong alkaline medium. Oxidation of ethane-1,2-diol, glycol aldehyde, glycollic acid, and glyoxylic acid. Int J Chem Kinet 24:145–154

Al-Hossainy AF, Ibrahim SM (2021) Oxidation process and kinetics of bromothymol blue by alkaline permanganate. Int J Chem Kinet 53:675–684

Jaky M, Kozhevinikov IV, Hoft E (1992) Oxidation with permanganate in strong alkaline medium. Oxidation of pyruvic and lactic acids. Int J Chem Kinet 24:1055–1065

Simandi LI, Jaky M, Savage SR, Schelly ZA (1985) Kinetics and mechanism of the permanganate ion oxidation of sulfite in alkaline solutions. The nature of short-lived intermediates. J Am Chem Soc 107:4220–4224

Chang HS, Korshin GV, Fargusun JF (2006) Examination of reaction mechanisms and reaction products for the oxidation of EDTA by permanganate at high pH values. Envir Sci Technol 40:5089–5094

Jaky M, Szammer J, Es T (2000) Kinetics and mechanism of the oxidation of ketones with permanganate ions. J Chem Soc Perkin Trans 2:1597–1602

Wiberg KB, Geer RD (1966) The Kinetics of the permanganate oxidation of alkenes. J Am Chem Soc 88:5827–5832

Taylor S, Halpern J (1959) Kinetics of the permanganate oxidation of formic acid and formate ion in aqueous solution. J Am Chem Soc 81:2933–2937

Wiberg KB, Freeman F (2000) Kinetics of the base-catalyzed permanganate oxidation of benzaldehyde. J Org Chem 65:573–576

Sharma K, Mehrotra RN (2002) Kinetics and mechanism of permanganate oxidation of phenylphosphinic acid in acid perchlorate solution. Ind J Chem Sec A 41:270–278

Hassan RM, Dahy AR, Ibrahim SM, Zaafarany IA, Fawzy A (2012) Oxidation of some macromolecules. Kinetics and mechanism of oxidation of methyl cellulose polysaccharide by permanganate ion in acid perchlorate solutions. Ind Eng Chem Res 51:5424–5432

Ibrahim SM, Al-Hossainy AF (2020) Kinetics and mechanism of oxidation of bromothymol blue by permanganate ion in acidic medium: Application to textile industrial wastewater treatment. J Mol Liq 318:114041–114048

Hassan RM, Ibrahim SM, Khairou KS (2018) Kinetics and mechanism of oxidation of pyruvate by permanganate ion in aqueous perchlorate solution. Trans Met Chem 43:683–691

Hassan RM, Ibrahim SM, Sayed SA (2018) Kinetics and mechanistic aspects on electron-transfer process for permanganate oxidation of poly(ethylene glycol) in aqueous acidic solutions in the presence and absence of Ru(III) catalyst. Int J Chem Kinet 50(2018):775–783

Insaustri MJ, Perez-Benito JK, Macho MR (1995) Kinetic study of the oxidation of L-phenylalanine by potassium permanganate in acid medium. Int J Chem Kinet 27:507–515

Manhas MS, Mohamed F, Khan, (2007) A kinetic study of oxidation of β-cyclodextrin by permanganate in aqueous media. Z Coll Surf A 295:165–171

Jaky M, Szammer J, Trompler ES (2006) Kinetics and mechanism of the oxidation of acetylacetone by permanganate ion. Inter J Chem Kinet 38:444–450

Hassan RM, El-Gaiar SA, El-Summan AM (1993) Kinetics of oxidation of selenium (IV) by permanganate ion in perchlorate solutions. Collect Czech Chem Commun 58:538–546

Hassan RM (1992) Kinetics and mechanism of oxidation of kojic acid by permanganate ion in perchlorate media. Acta Chim Hungar 129:661–669

Hassan RM (1991) Kinetics and mechanism of oxidation of DL-α-alanine by permanganate ion in acid perchlorate media. Can J Chem 69:2018–2023

Hassan RM, Mousa MA, Wahdan MH (1988) Kinetics and mechanism of oxidation of p-phenylalanine by permanganate ion in aqueous perchloric acid. J Chem Soc Dalton Trans 3:605–609

Hassan RM (1988) Mousa MA, El-Shatoury SA (I985) Kinetics of the oxidation of uranium (IV) by permanganate ion in aqueous perchlorate media. J Chem Soc Dalton Trans 3:601–603

Hassan RM, Ibrahim SM (2019) Kinetics and mechanism of permanganate oxidation of ADA in aqueous perchlorate solutions. Current Organocatalysis 6:52–60

Hassan RM, Takagi HD, Ibrahim SM (2020) Orientation on the mechanistic of electron-transfer on oxidation of chondroitin-4-sulfate as sustainable sulfated polysaccharide by permanganate ion in aqueous perchlorate solutions. J Renew Mater 8:205–218

Hussain MY, Ahmed F (1990) Kinetics and mechanism of oxidation of DL-leucine by acid permanganate. Trans Met Chem 15:185–190

Freeman F, Lin DK, Moore GR (1982) Permanganate ion oxidations. 14. Kinetics and mechanism of the oxidation of aliphatic aldehydes in acid media. J Org Chem 47:56–59

Rao PV (1971) Kinetics of oxidation of ethyl acetate by potassium permanganate. Z Phyz Chemie Leipzig 246:352–356

Banoo F, Stewart R (1969) Permanganate oxidation of aromatic alcohols in acid solution. Can J Chem 47:3199–3205

Lee DG, Chen T (1989) Oxidation of hydrocarbons. 18. Mechanism of the reaction between permanganate and carbon-carbon double bonds. J Am Chem Soc III:7534–7538

Girgis MM, El-Shatoury SA, Khalil ZH (1985) Kinetics and mechanism of oxidation of lactic acid by KMnO4 in H2SO4 medium. Can J Chem 63:3317–3321

Mehrotra RN (1984) Kinetics and mechanisms of redox reactions in aqueous solution. Part 9. Permanganate oxidation of phosphorous acid in perchlorate solution. J Chem Soc Dalton Trans 1:1531–1535

Sen PK, Mukhopadhyay G, Sen Gupta KK (1998) Kinetics and mechanism of the oxidation of alkyl and aryl methyl ketones by permanganate ion in aqueous ethanoic acid. Trans Met Chem 23:577–582

Ghosh A, Datta I, Ghatak S, Mahali K, Bhattacharyya SS, Saha B (2016) Picolinic acid promoted permanganate oxidation of D-mannitol in micellar medium. Tenside, Surfactants, Deterg 53:332–346

Sen PK, Mukhopadhyay G, Gant N, Sen Gupta KK (2001) Relative reactivities of 1,2-dicarbonyl compounds towards permanganate in ethanoic acid medium. Mechanism of the oxidation processes. Trans Met Chem 26:451–456

Hicks KW, Chappele GA (1980) Rates and equilibria of organic reactions. Inorg Chem 19:1623–1625

Mucientes A, Poblete FJ, Casado J (1991) Kinetic study of the permanganate oxidation of DL-valine in acidic media. React Kinet Catal Lett 43:249–254

Tomas L, Hicks KW (1974) Kinetics of the permanganate ion-potassium octacyanomolybdate(IV) reaction. Inorg Chem 13:749–752

Wiberg K, Stewart R (1956) The mechanisms of permanganate oxidation. II. The oxidation of formate ion. J Am Chem Soc 78:1214–1216

Lawni SA, Sutter JR (1973) Kinetic studies of permanganate oxidation reactions. IV. Reaction with bromide ion. J Phys Chem 77:1547–1551

Hicks KW, Sutter JR (1971) Kinetic studies of permanganate oxidation reactions. III. Reaction with tris(1,10-phenanthroline)iron(II). J Phys Chem 75:1107–1113

Raouf MA, Sutter JR (1967) Kinetic studies of permanganate oxidation reactions. II. Reaction with ferrocyanide ion. J Phys Chem 71:2767–2771

Kirschenbaum LJ, Sutter JR (1966) Kinetic studies of permanganate oxidation reactions. I.Reaction with Iodide Ion. J Phys Chem 70:3863–3866

Ghosh A, Sengupta K, Saha R, Saha B (2014) Effect of CPC micelle on Nhetero-aromatic base promoted room temperature permanganate oxidation of 2-butanol in aqueous medium. J Mol Liq 198:369–380

Bailey N, Carrington A, Symons MCR (1960) 55 Structure and reactivity of the oxyanions of transition metals. Part VIII. Acidities and spectra of protonated oxyanions. J Chem Soc 1:290–297

Millazzo G, Caroll S, Sharma VK Tables of Standard Potential, Wiley, New York, 1978; Latimer, W.“Oxidation Potentials”, 2nd Edn., Prentice-Hill, Englewood Cliffs, Nj, 1952.

Hassan RM (1993) Alginate polyelectrolyte ionotropic gels. XIV. Kinetics and mechanism of formation of intermediate complex during the oxidation of alginate polysaccharide by alkaline permanganate with a spectrophotometric evidence of manganate(VI) transient species. J Poly Sci Part A 31:51–59

Hassan RM (1993) Alginate polyelectrolyte ionotropic gels. XVIII. Oxidation of alginate polysaccharide by potassium permanganate in alkaline solutions. Kinetics of decomposition of the intermediate complex. J Poly Sci Part A 31:1147–1151

Khairou KS, Hassan RM (2000) Pectate polyelectrolyte ionotropic gels. I. Kinetics and mechanism of formation of manganate (VI)-pectate intermediate complex during oxidation of pectate polysaccharide by alkaline permanganate. Eur Poly J 36:2021–2030

Khairou KS (2003) Kinetics and mechanism of decomposition of intermediate complex during oxidation of pectate polysaccharide by potassium permanganate in alkaline solutions. Inter J Chem Kinet 35:67–72

Hassan RM, Ibrahim SM (2019) Novel synthesis of coordination biopolymer precursor from oxidation of methyl cellulose by alkaline potassium permanganate. Integr Food, Nutr Metab 6:1–5

Shaker AM, Abd-Mohsen E-K, L, Nassr E, (2009) Further mechanistic orientation for the oxidation reaction between alkaline permanganate and poly galacturonate methyl ester. Novel spectrophotometric tracer of intrahypomanganate(V) – Intermediate. Carbohyd Poly 78:710–716

Abd-Mohsen L, Nassr E (2010) Kinetics and mechanism of disproportionation of Mn(VI)O42− induced by decomposition of intramanganato-polygalacturonate methyl ester coordination polymer precursor: Medium-substituent effects on reactivity. Carbohyd Poly 82:880–886

El-Khatib RM (2002) Spectrophotometric detection of methyl cellulose–manganate(VI) intermediate complex in the oxidation of methyl cellulose by alkaline permanganate. Carbohyd Poly 47:377–385

Shaker AM, El-Khatib RM, Mahran HS (2007) Kinetics and mechanism of the decay of methyl cellulose - manganate (VI) polysaccharide transient species–novel spectrophotometric kinetic trace of methyl cellulose hypomangate (V) gel intermediate polysaccharide. J Appl Poly Sci 106:2668–2674

Shaker AM (2001) Base catalyzed oxidation of carboxymethyl cellulose polymer by permanganate. I-Kinetics and mechanism of formation of manganate (VI) transient species complexes. J Colloid Interface Sci 233:197–204

Shaker AM (2001) Novel Carboxymethyl Cellulose Ionotropic Gels: II. Kinetics of Decomposition of the Manganate (VI) Intermediate-Novel Spectrophotometric Tracer of the Preformed Short Lived Hypomanganate(V) Coordination Polymer Sol. J Colloid Interface Sci 244:254–261

Ahmed G, Fawzy A, Hassan RM (2007) Spectrophotometric evidence for the formation of short-lived hypomanganate (V) and manganite (VI) transient species during the oxidation of K-carrageenan by alkaline permanganate. Carbohyd Res 342:1382–1386

Zaafarany A, Al-Arifi ASN, Fazy A, Ibrahim SA, Hassan RM, Takagi HD (2010) Further evidence for detection of short-lived transient hypomanganate (V) and manganite (VI) intermediates during oxidation of some sulfated polysaccharides by alkaline permanganate using conventional spectrophotometric techniques. Carbohyd Res 345:1588–1593

Hassan RM, Ibrahim SM, Fawzy A (2020) Novel synthesis of coordination bipolymer precursors of sulfated macromolecules as alternative promising in biomedicine, pharmaceutics and engineering industry by oxidation of sustainable and biodegradable sulfated iota-carrageenan by alkaline permanganate. Nanomedicine 3:1026–1029

Hassan RM (2022) Novel synthesis of ketoacid precursor derivative for oxidation of lambda-carrageenan polysaccharide as alternative promising in pharmaceutics, medicine, biomedicine and biotechnology applications. Int J Pharma phytopharm 11:41–48

Zaafarany IA, Gobouri AA, Hassan RM (2013) Oxidation of some sulfated carbohydrates: Kinetics and mechanism of oxidation of chondroitin-4-sulfate by alkaline permanganate with novel synthesis of coordination biopolymer precursor. J Mater Sci Res 2:23–28

Hassan RM (1993) New coordination polymers. III: Oxidation of poly(vinyl alcohol) by permanganate ion in alkaline solutions. Kinetics and mechanism of formation of intermediate complex with a spectrophotometric detection of manganate (vi) transient species. Poly Inter 30:5–9

Hassan RM, El-Gaiar SA, El-Summan AM (1993) New coordination polymers. IV. Oxidation of poly (vinyl alcohol) by permanganate ion in alkaline solutions. Kinetics and mechanism of decomposition of intermediate complex. Poly Inter 32:39–42

Hassan RM, Sayed SA, Ibrahim SM (2021) Base-catalyzed oxidation of poly (ethylene glycol) by alkaline permanganate: Part I. Kinetics and mechanistic of formation of coordination intermediate complex. J Petrol Chem 30:1–7

Hassan RM, Sayed SA, Ibrahim SM (2021) Base-catalyzed oxidation of poly (ethylene glycol) by alkaline permanganate: Part II. Kinetics and mechanistic of decomposition of coordination intermediate complex. J Petrol Chem 30:1–6

Davison ED (1967) Carbohydrate Chemistry”. Holt, Rinehart and Winston, New York

Fisher FG, Dorfel H (1965) The polyuronic acids in brown algae. Z Physiol Chem 302:186–203

Muzzaralli RAA (1973) Natural Chelating Polymers, 1st edn. Pergamon Press, Oxford, New York

Davidson RL (1980) Handbook of Water-Soluble Gums and Resins”. McGraw-Hill, New York

Rees DA (1972) Shapely polysaccharides. The eighth colworth medal lecture. Biochem J 126:257–273

Pearson RG (1977) From rate laws to reaction mechanisms. J Phys Chem 81:2323–2328

Hassan RM, Ibrahim SM (2020) Orientation on the mechanistics of electron-transfer on oxidation of chondroitin-4-sulfate as sustainable sulfated polysaccharide by permanganate ion in aqueous perchlorate solutions. J Renew Mater 8:205–218

Hassan RM, Abd-Alla MA, El-Zohary MF (1993) Alginate polyelectrolyte ionotropic gels. VI. Novel synthesis of diketoalginate as bipolymer precursor. J Appl Poly Sci 47:1649–1652

Forst AA, Pearson RG, Kinetics and Mechanism, 2nd Edn., Wiley, New York, 1961; Basolo, F.; Pearson, R.J. “Mechanisms of Inorganic Reactions”, 2nd Edn., Wiley, New York, 1967.

Pearson RG (1976) Symmetry Rates for Chemical Reactions. Wiley Inter-Science, New York

Feigl F (1960) Spot Tests” in Organic Analysis. El Sevier, London

Malik MA, Llyas M, Khan Z (2009) Kinetics of permanganate oxidation of synthetic macromolecule poly(vinyl alcohol). Ind J Chem 48:189–193

Wiberg KB, Deutsch CJ, Rocek J (1973) Permanganate oxidation of crotonic acid. Spectrometric detection of an intermediate. J Am Chem Soc 95:3034–3035

Stewart R (1965) Oxidation in Organic Chemistry, KB, Wiberg. Academic Press, New York, Part A., p 48

Zimmerman CL, Thesis University of Chicago, 1949.

Lee DG, Brownridge RJ (1974) Oxidation of hydrocarbons. IV. Kinetics and mechanism of the oxidative cleavage of cinnamic acid by acidic permanganate. J Am Chem Soc 96:5517–5523

Chandler D, Anderson HC (1972) Optimized cluster expansions for classical fluids. II. Theory of molecular liquids. J Phys Chem 57:1930–1937

Freeman F, Fuseller CO, Armstead CR, Dalton CE, Davidson PA, Karchefski EM, Krochman DE, Johnson MN, Jones NK (1981) Permanganate ion oxidations. 13. Soluble manganese(IV) species in the oxidation of 2,4(1H,3H)-pyrimidinediones (uracils). J Am Chem Soc 103:1154–1159

Sullivan J (1964) The Formation of a neptunium (V)-chromium (III) complex Kinetics and equilibria in perchlorate solutions. Inorg Chem 3:315–319

Ekestrom A, Farrar Y (1972) Kinetics and mechanism of the formation of the chromium (III).uranium (V) binuclear complex. Inorg Chem 11:2610–2615

Makhlouf MTh, El-Shatoury SA, Hassan RM (1992) Alginate polyelectrolyte ionotropic gels. XIX. Spectrophotometric detection of short-lived intermediate in alkaline permanganate oxidation of alginate polysaccharide. High Perform Poly 4:89–96

El-Azhary S, Hassan RM (1999) Spectrophotometric detection of short-lived manganate(VI) intermediate through oxidation of some natural and synthetic polymers by alkaline permanganate. Spectr Lett 32:17–29

Khairou KS (2001) Spectrophotometric evidence for the formation of short-lived Mn(VI) as transient species intermediate during the permanganate oxidation of chitin and chitosan polysaccharides in alkaline solutions. Spectr Lett 34:117–124

Fatiadi AJ (1987) The Classical permanganate ion: Still a novel oxidant in organic chemistry. Synthesis 2:85–127

Lee DG (1982) Oxidation in Organic Chemistry, Part D, W. S. Trahanovsky, (Edn.). Academic Press, New York, 147.

Lee DG, Lee EJ, Brown KC, Phase Transfer Catalysis, New Chemistry, Catalysis and Application, ACS Symposium Series No 326, Washington, 1987.

Sharpless KP, Teranishi AY, Backvall JE (1977) Chromyl chloride oxidations of olefins. Possible role of organometallic intermediates in the oxidations of olefins by oxo transition metal species. J Am Chem Soc 99:3120–3128

El-Shatoury SA, Mahfouz RM, Hassan RM (1995) Alginate Polyelectrolyte Ionotropic Gels X Reaction of Ketoalginate with Polyvalent Metal Ions with Special Evidence on the Nature of Chelation. Asw Sci Tech Bull Egypt 16:51

Hassan RM, El-Gahami MA, Abd-Alla MA (1992) New coordination polymers. II. Coordination of poly (vinyl alcohol) with divalent metal ions. J Mater Chem 2:613–615

Gardner KA, Kuehnert LL, Mayer JM (1997) Hydrogen atom abstraction by permanganate: oxidations of arylalkanes in organic solvents. Inorg Chem 36:2069–2078

Harkness AC, Halpern H (1959) Kinetics of the oxidation of uranium (IV) by thallium (III). J Am Chem Soc 81:3526–3529

Shastri NK, Amis ESWear JO, (1965) Kinetics of the reduction of neptunium (V) with uranium (IV) in aqueous perchlorate and chloride media. J Inorg Nucl Chem 27:2413–2422

Hassan RM (1992) Oxidation of uranium (IV) by polyvalent metal ions. A Linear free- energy correlation. Coord Chem 27:255–266

Ondrus MG, Gordon G (1972) Oxidation of hexaaquoiron (II) by chlorine(III) in aqueous solution. Inorg Chem 11:985–989

Glasstone S, Laidler KJ, Eyring H (1941) The Theory of Rate Processes. McGraw-Hill Book C, New York

Sutin N (1968) Free energies, barriers, and reactivity patterns in oxidation-reduction reactions. Acad Chem Res 1:225–231

Hicks KW, Toppen DL, Linck RG (1972) Inner-sphere electron-transfer reactions of vanadium (II) with azidoamine complexes of cobalt (III). Inorg Chem 11:310–315

Al-Hossainy AF, Ibrahim SM (2021) Oxidation process and kinetics of bromothymol blue by alkaline permanganate. Inter J Chem Kin 53:675–684

Sullivan JC, Hindman JC (1959) The Hydrolysis of neptunium(IV). J Phys Chem 63:1332–1333

Moore FM, Hicks KW (1975) Mechanism of the permanganate ion oxidation of vanadium(IV). Inorg Chem 14:413–416

Stewart R (1957) The mechanisms of permanganate oxidation. III. The oxidation of benzhydrol. J Am Chem Soc 79:3057–3061

Stewart R, Maden RV (1960) The mechanism of the permanganate oxidation of fluoro alcohols in aqueous solution. Discuss Farad Soc 29:211

Stewart R, Rocek MM (1963) The mechanisms of permanganate oxidation: VII. The oxidation of Fluoral hydrate. Can J Chem 41:1160–1169

Leffler L, Grunwald E (1963) Rates and Equilibria of Organic Reactions. Wiley, New York