Alkaline Fading of Malachite Green in β-Cyclodextrins

Anton Soria-Lopez; Raquel Rodriguez-Fernández; Juan C. Mejuto

doi:10.3390/compounds4020019

journal article Open Access May 13, 2024

Alkaline Fading of Malachite Green in β-Cyclodextrins

Anton Soria-Lopez

Raquel Rodriguez-Fernández Juan C. Mejuto

Compounds Vol. 4 No. 2 pp. 351-360 · MDPI AG

View at Publisher Save 10.3390/compounds4020019

Abstract

The basic hydrolysis of Malachite Green (MG) in the presence of β-Cyclodextrin (β-CD) has been studied using UV-Vis spectroscopic techniques and at 20 °C. β-CD was found to catalyze the basic hydrolysis. Indeed, this basic hydrolysis is catalyzed by the interaction cyclodextrin hydroxyl group, in its deprotonated form with the carbocation in the host-guest complex. The proposed model has been successfully applied to a reaction catalyzed by CD. It considers two simultaneous pathways in the aqueous medium involving free hydroxyl ions and the substrate-CD complex. The model allows us to obtain the kinetic parameters including the bimolecular rate constant between MG and HO− in bulk water (kw = 1.47 ± 0.01 mol−1s−1), the rate constant between MG and the deprotonated hydroxyl group of β-CD inside the host-guest complex (kCD = 0.25 ± 0.03 s−1) and the binding constant of MG inside the β-CD (KS = 2500 ± 50). This behavior is like the hydrolysis of Cristal Violet (CV) in the same reaction media.

Topics

No keywords indexed for this article. Browse by subject →

References

35

[1]

Mejuto, J.C., and Simal-Gandara, J. (2022). Host-Guest Complexes. Int. J. Mol. Sci., 23. 10.3390/ijms232415730

[2]

Review: A History of Cyclodextrins

Grégorio Crini

Chemical Reviews 2014 10.1021/cr500081p

[3]

Mellet "Cyclodextrin-Based Gene Delivery Systems" Chem. Soc. Rev. (2011) 10.1039/c0cs00019a

[4]

Saenz "Mining for Novel Cyclomaltodextrin Glucanotransferases Unravels the Carbohydrate Metabolism Pathway via Cyclodextrins in Thermoanaerobacterales" Sci. Rep. (2022) 10.1038/s41598-021-04569-x

[5]

Kinart, Z. (2023). Conductometric Studies of Formation the Inclusion Complexes of Phenolic Acids with β-Cyclodextrin and 2-HP-β-Cyclodextrin in Aqueous Solutions. Molecules, 28. 10.3390/molecules28073113

[6]

The Stability of Cyclodextrin Complexes in Solution

Kenneth A. Connors

Chemical Reviews 1997 10.1021/cr960371r

[7]

Bortolus "Photochemistry of Cyclodextrin Host-Guest Complexes" Coord. Chem. Rev. (1993) 10.1016/0010-8545(93)85023-w

[8]

Lehn "Supramolecular Chemistry" Science (1993) 10.1126/science.8511582

[9]

Steed, J.W., and Atwood, J.L. (2013). Supramolecular Chemistry, Wiley. [2nd ed.].

[10]

Iglesias, E., and Fernández, A. (1998). Cyclodextrin Catalysis in the Basic Hydrolysis of Alkyl Nitrites. J. Chem. Soc. Perkin Trans. 2, 1691–1700. 10.1039/a707647i

[11]

Thakur, N., Thakur, N., Kumar, K., Arya, V., and Kumar, A. (2023). Encapsulation of Tinospora Cordifolia Plant in Ni Doped TiO2 Nanoparticles for the Degradation of Malachite Green Dye. Nanofabrication, 8. 10.37819/nanofab.8.305

[12]

Yan "Screening of Trametes Strains for Efficient Decolorization of Malachite Green at High Temperatures and Ionic Concentrations" Int. Biodeterior. Biodegrad. (2014) 10.1016/j.ibiod.2013.11.009

[13]

Lie, Ø. (2008). Improving Farmed Fish Quality and Safety, Woodhead Publishing. 10.1533/9781845694620

[14]

Dasmandal "Kinetic Investigations on Alkaline Fading of Malachite Green in the Presence of Micelles and Reverse Micelles" J. Mol. Liq. (2014) 10.1016/j.molliq.2013.12.017

[15]

Gessner, T., and Mayer, U. (2000). Ullmann’s Encyclopedia of Industrial Chemistry, John Wiley & Sons, Ltd.

[16]

Toxicological effects of malachite green

Shivaji Srivastava, Ranjana Sinha, D. Roy

Aquatic Toxicology 2004 10.1016/j.aquatox.2003.09.008

[17]

Willoughby "Towards Strategic Use of Fungicides against Saprolegnia Parasitica in Salmonid Fish Hatcheries" J. Fish Dis. (1992) 10.1111/j.1365-2761.1992.tb00631.x

[18]

Diggles "A Mycosis of Juvenile Spiny Rock Lobster, Jasus edwardsii (Hutton, 1875) Caused by Haliphthoros Sp., and Possible Methods of Chemical Control" J. Fish Dis. (2001) 10.1046/j.1365-2761.2001.00275.x

[19]

Lilley "Comparative Effects of Various Antibiotics, Fungicides and Disinfectants on Aphanomyces Invaderis and Other Saprolegniaceous Fungi" Aquac. Res. (1997) 10.1111/j.1365-2109.1997.tb01064.x

[20]

Deokar "Biosorption of Methylene Blue and Malachite Green From Binary Solution onto Ulva Lactuca" Int. J. Curr. Microbiol. App. Sci. (2014)

[21]

Hema "Adsorption Kinetics and Thermodynamics of Malachite Green Dye unto Acid Activated Low Cost Carbon" J. Appl. Sci. Environ. Manag. (2008)

[22]

Samiey "Kinetics Study of Malachite Green Fading in the Presence of TX-100, DTAB and SDS" Bull. Korean Chem. Soc. (2009) 10.5012/bkcs.2009.30.9.2051

[23]

Leis "Comparison between the Kinetics of the Alkaline Fading of Carbocation Dyes in Water/Sodium Bis (2-Ethylhexyl) Sulfosuccinate/Isooctane Microemulsions and in Homogeneous Media" Langmuir (1993) 10.1021/la00028a003

[24]

Dasmandal "Kinetic Exploration Supplemented by Spectroscopic and Molecular Docking Analysis in Search of the Optimal Conditions for Effective Degradation of Malachite Green" RSC Adv. (2015) 10.1039/c5ra04724b

[25]

Ritchie "Nucleophilic Reactivities toward Cations" Acc. Chem. Res. (1972) 10.1021/ar50058a005

[26]

Saenger "Cyclodextrin Inclusion Compounds in Research and Industry" Angew. Chem. Int. Ed. Engl. (1980) 10.1002/anie.198003441

[27]

Felix "Kinetics and Thermodynamic Study of Alkaline Fading of Malachite Green in Aqueous Solution" J. Appl. Fundam. Sci. (2017)

[28]

Dalal, M. (2018). A Textbook of Physical Chemistry. Volume I, Dalal Institute.

[29]

Laider, K.J. (1987). Chemical Kinetics, Pentice Hall. [3rd ed.].

[30]

Leis "Kinetic and Spectroscopic Evidence for the Formation of Ion-Pairs between Crystal Violet and Perchlorate Ion" J. Chem. Res. (1997)

[31]

Leis "Basic Hydrolysis of M-Nitrophenyl Acetate in Micellar Media Containing β-Cyclodextrins" J. Phys. Chem. B (1998) 10.1021/jp980432k

[32]

Alvarez "Basic Hydrolysis of Substituted Nitrophenyl Acetates in β-Cyclodextrin/Surfactant Mixed Systems. Evidence of Free Cyclodextrin in Equilibrium with Micellized Surfactant" Langmuir (1999) 10.1021/la981392e

[33]

Astray "Alkaline Fading of Triarylmethyl Carbocations in Self-Assembly Microheterogeneous Media" Prog. React. Kinet. Mech. (2011) 10.3184/146867811x12984793755693

[34]

Leis "Basic Hydrolysis of Crystal Violet in β-Cyclodextrin/Surfactant Mixed Systems" Langmuir (2004) 10.1021/la035477d

[35]

Rezanka, M. (2018). Cyclodextrin Fundamentals, Reactivity and Analysis, Springer.

Metrics

1

Citations

35

References

Details

Published: May 13, 2024
Vol/Issue: 4(2)
Pages: 351-360
License: View

Authors

A

Anton Soria-Lopez

Department of Physical Chemistry, Faculty of Science, University of Vigo at Ourense, Campus de As Lagoas, 32004 Ourense, Spain

R

Raquel Rodriguez-Fernández

Department of Physical Chemistry, Faculty of Science, University of Vigo at Ourense, Campus de As Lagoas, 32004 Ourense, Spain

J

Juan C. Mejuto

Department of Physical Chemistry, Faculty of Science, University of Vigo at Ourense, Campus de As Lagoas, 32004 Ourense, Spain

Cite This Article

Anton Soria-Lopez, Raquel Rodriguez-Fernández, Juan C. Mejuto (2024). Alkaline Fading of Malachite Green in β-Cyclodextrins. Compounds, 4(2), 351-360. https://doi.org/10.3390/compounds4020019

Alkaline Fading of Malachite Green in β-Cyclodextrins

You May Also Like