CC BY
1
CHEMICAL PROBLEMS 2025 no. 2 (23) ISSN 2221-8688
239
CHLORINATION OF N-BENZOYL VALINE BY SODIUM N-CHLORO-PARA-TOLUENE SULFONYL AMIDE (CAT) HYDROCHLORIC ACIDIC: A KINETIC AND MECHANISM
STUDY
Alaa M.A. Hasb, Noor H.M. Saeed
Department of Chemistry, College of Education for Pure Science, University of Mosul, Mosul, Iraq
e-mail: shimarb@,uomisan.edu.iq
Received 17.05.2024 Accepted 23.07.2024
Abstract. The mechanism of N-benzoyl valine oxidation by chloramine-T in hydrochloric acid medium at temperatures ranging from 308 to 328 K is the subject of this research. The findings of the experiment showed that the medium's ionic strength had an influence, as the affixing of P-toluene sulphone amide slightly retarded the reaction, and that the reaction was first order with regard to the substrate and chloramine-T. Based on kinetic investigations, the reaction ratio 1:1 is suggested. Keywords: Chlorination, N-benzoyl Valine, (CAT), kinetic. DOI: 10.32737/2221-8688-2025-2-239-248
1. Introduction
Kinetic studies have been conducted on the mechanism of many oxidation processes of sodium N-chloro-4-methyl benzene Sulfonamide p-CH3-C6H4 SO2NClNa3H2O, also recognized as (CAT) chloramine-T; under both acidic and alkaline condition, it acts as an oxidizing agent, producing sodium chloride and p-toluene sulphone amide. Chloramine-T provides a number of active species, including RNHCl, HOCl, and RNCl, OCl- ions in an alkaline medium and DCT (Dichloramine-T) in an acidic solution [1]. The type of oxidized material determines which of these components is more effective, and altering the experimental setup typically increases the effectiveness of one component over the other. Some research has studied the behavior of using chloramine-T as an oxidant [2-4]. The Ir(III) catalyst is used for oxidation of Leucine [5] L-Alanine [6], mannitol [7], and Fructose [8] by chloramine-T. Several kinetics investigations have been carried
out with this oxidizing agent such as oxidation of some aromatic attic primary diamines in the presence of HCl [9], thiourea and N-substituted thiourea [10], amide [11], carboxylic acid [12], alcohol [13], tetrahyrofuran [14], ether [15] and chlorination of N-acetyl glycine [16] and alanine [17]. Due the amino acids are essential for metabolism in addition to being building blocks for protein synthesis, amino acid oxidation is a biological process of great interest. The kinetics and mechanism of amino acid oxidation in various applications in biochemical research have been studied by many researchers [18]. Furthermore, amino acid oxidation is interesting because different oxidants lead to the formation of different products one of the biochemical progresses. Using various oxidants amino acid oxidation and kinetics have been extensively studied. On the other hand, the literature on N-benzoyl valine oxidation has relatively few reports.
2. Experimental Part
Materials. All chemicals that were used Spectrophotometer Shimadzu UV-1800 PC, in the manuscript were produced by Alpha Acer UV-Visible was used. BDH and Sigma Aldrich companies. A Methods.
spectrophotometer Double beam -
www.chemprob.org
CHEMICAL PROBLEMS 2025 no. 2 (23)
Synthesis of Chloramine - T [19, 20].
The procedure was used to prepare and purify chloramine-T A chloramine-T aqueous solution. It is kept in stoppered amber bottles and is standardized using the iodometric method.
Synthesis of N- benzoyl valine [21, 22]. Dissolving 1 mole of the amino acid (valine) in the solution of 10% NaOH and cooling at -5 to -10 °C, added 1 mole of benzoyl chloride
gradually with continuous stirring and finally the medium was neutralized, the white precipitate was filtered and dried. Obtained a yellow powder with a yield of 78%, and m.p. (130-132)oC.
IR (cm-1): 3323 (N-H), 3070 (C-Harm), 2995, 2826 (C-Halph), 1748 (c=O) acid, 1678 (C=O) amide, 1275 (C-O) acid (Fig.1).
Fig.1. IR spectrum for prepared compound (N-B-V)
Kinetic measurements [23, 24]. Pseudo first-order conditions were used to conduct the reactions in Pyrex at 308 K using a known substrate excess over an oxidant. The necessary quantities of substrate solutions for each run. To maintain a constant total volume during all runs, HCl, NaClO4, and water were placed within the tube and thermostat at 308 K. The measured amount of CAT solution was thermostat at the same temperature. Following the reaction, 2 ml of the mixture was taken out and added to a flask including potassium iodide and 2M of sulfuric acid to quench the reaction.
Iodine that was titrated against a
conventional sodium thiosulphate solution as titrant using starch as an indicator is liberated when the unreacted chloramine-T rapidly reacts with the KI solution. after this reaction, the free iodine was measured spectrophotometrically at a wavelength of 353 nm.
Stoichiometry. Different ratios of CAT to N-benzoy1 Valine were equilibrated in the Company of 0.2 (M) of HCl, water, and ethanol, at 308 K for 24 hours. Determination of the remaining Oxidant demonstrated that 1moles of chloramine-T was consumed Per mole of N-benzoyl Valine the chemical measurements obtained can be represented as follows:
o o o o
II H H II H+ II H II Ph—c—N—c— c—OH + RNCl.Na + H20-^ Ph—C—N—C—C—OH.........(1)
I II
R CI R
^-toluene sulfonamide was detected Among the products of the reaction using paper solvent by chromatography [25], The resulting N-chlorobenzoyl valine was identified as an alight crystal by infrared spectroscopy (cm-1): 3063
(C-Harm), 2922 (C-Halph), 1741 (C=O) acid , 1655 (C=O) amide , 1300 (C-O) acid In addition to (812,659) cm-1 of the (N-Cl)bond [26], Note that the stretch band (NH) has disappeared (Fig.
2) at m.p. (106-108) °C and from chlorine elemental analysis testing.
Fig. 2. IR spectrum for product chlorination compound ( N-B-V)
3. Results and Discussion
At various initial reactant concentrations kinetics of the chlorination of N-benzoyl valine by CAT has been investigated in the hydrochloric acid media at 308 K.
The effect of different concentrations of reactants on the reaction rate. Plotting the log CAT versus time at constant acid concentration
and excess substrate concentration was linear (r > 0.99 54) (Fig.3), It suggests that [CAT] has a first-order rate dependence. The pseudo-order of rate constant is included in Table 1 the values of which are unaffected by increasing substrate concentration, showing that the [N-B.V.] concentration had no effect on the reaction rate.
Fig. 3. Graph log [CAT] versus Time for oxidation of N-benzoyl Valine at 308 K.
Table 1. The effect of variation [N-B.V.] and [CAT] concentration at 308 K, [HC1]=0.05M,
M=0.025 M, 25% ethanol.
103CAT] M 103[S] M 104 k Sec-1
1.50 0.75 9.7871
1.50 1.00 9.8640
1.50 1.25 9.8265
1.50 1.50 9.7871
1.50 1.75 9.8265
1.25 1.00 11.9754
1.50 1.00 9.8640
1.75 1.00 8.6743
2.00 1.00 7.6765
2.25 1.00 6.4480
The effect of different concentrations of hydrogen and chloride ions. On varying the concentration of hydrochloric acid from (0.03-0.ll ) M Table 2, it was observed that an increase in reaction rate when increasing the concentration of hydrogen ion. Graphing log k against [H+] got a straight line (Fig. 4). Consequently, the first-order reliance on hydrogen concentration is shown, while the rate constant of reaction will intensify slightly with a
rise in [Cl-] concentration (Table 2). Plotting the log k versus [Cl-] gives straight line with an 0.2 slope. The increase the rate constant is the creation of HOCl as a result of the way in which the chloronium and chloride ions interact generated by the N-Cl bond's hydrolysis accelerates the rate of reaction. The reason for the increase in the rate of reaction is causes the formation of HOCl based on the reaction that follows [27].
RNHC + Cl ^ RNHCl - Cl RNHCl - Cl ^ RNH - +Cl2 Cl, + HO ^ HOCl + HCl
(2)
(3)
(4)
Therefore increasing the concentration of chloride ions produces more the reaction's
active oxidizing species (i.e. HOCl), and as a result, the reaction rate is seen to increase [28].
Fig. 4. Graph Log K Versus Log [H+] for oxidation of N-benzoyl Valine at 308 K
Table 2. Effect of variation of hydrochloric acid [H+] and Sodium chloride [Cl-] concentration at 308 K [CAT]=0.0015 M; [N-B.V.]= 0.0, M=0.025 M; 25% Ethanol
102[H+] M 102[Cl-] M 104 k
3.00 5.00 10.708
5.00 5.00 20.72
7.00 5.00 27.36
9.00 5.00 36.31
11.00 5.00 45.25
5.00 2.50 18.38
5.00 5.00 20.72
5.00 7.50 22.99
5.00 10.00 24.56
5.00 12.50 27.48
Effect of changing of the Ionic strength additional p-toluene sulphone amide. The
rate of reaction was unaffected by incorporating concentrated sodium perchlorate solution to
change the medium of ionic strength (0.025-0.125M). Additionally, Table 3 shows that the addition of P-toluene sulphone amide (P-TSA) somewhat changed the rate of reaction [29].
Table3. Effect of variation of Product [P-TSA] and Sodium perchlorates NaClO4 of [N-B.V.] at
308 K°; [N- B.V.] = 0.01 M, [CAT]=0.0015, [H]=0.05 M, ethano 25%
102[NaClO4] M 104 k1 Sec-1 103[ p-TSA] M 104 k1 Sec-1
2.50 9.8640 1.00 9.5239
5.00 9.6431 2.00 9.2999
7.50 9.7851 3.00 8.9898
10.00 9.6134 4.00 8.7111
12.50 9.8123 5.00 8.3267
The effect of changing the medium's dielectric constant on the rate. Using ethanol (25%-55%) in the reaction solution changed the medium's dielectric constant (D), and the rate
constant's value increased as the ethanol amount increased (Table 4). Plots showing Log k versus I/D have a positive slope [30].
Table 4. Effect of varying the medium's dielectric constant on the rate reaction at 308 K,
[N-B.V.] =0.01M, [CAT]=0.0015, [H"]=0.05M
Ethanol V% D 104 k1 Sec-1
25.00 58.53 9.8640
35.00 53.22 11.2164
45.00 49.49 12.4365
55.00 43.97 13.6523
65.00 39.04 16.5412
The effect of temperature. The Arrhenius equation has been used to study the rate of reaction at various temperatures (308-323 K), and (Fig. 5) shows plotting of log k1 vs 1/T., it was observed that increasing the temperature increases the rate of reaction. activation energy
and its parameters of the compound were evaluated. These values are given in the Table 5. The values of activation enthalpy, entropy, and free energy suggest that the reaction's progress is not spontaneous [31].
1 6 •
1.4 •
IJ •
< 1 jj 0 8 04 V- 3.3579**11 787 R' - 0 .999 •
04
0.7 0 3
30b 3J 315 1000/T 3J 3.2S 33
Fig. 5. Plotting Log k vs. I/T of N-benzog Valine at Valine at 308 K
Table 5. Temperature's effect on reaction rate, [N-B.V.]=0.0M, [CAT]=00015M, [H+] = 0.05 M
=0.025
T; 104 k1; AH*; AS*; AG*; Log A;
K Sec-1 kJ/mole J/(moleK) kJ/mole Sec-1
308 9.8640 53.96739 -288.333 88.86068 7.581169
313 14.0860 53.92582 -307.316 96.24398 6.582569
318 18.5001 53.88425 -307.754 97.91981 6.552806
323 28.1101 53.84268 -306.898 99.182 6.590754
328 38.3440 53.80111 -306.858 100.7032 6.586187
Ea= 2.9871 x 103 kJ/mole AH (average) = 53.8842 kJ/mole AS# (average) = -303.432 J/(mole-K) AG# (average) = 96.5819 kJ/mole Log A (average) = 6.7786 Sec-1
Discussion. Chloramine-T was used as a moderate oxidizing agent in both alkaline and acidic conditions. In general, two electrons are exchanged in chloramine-T reactions to produce p-TSA (p-CH3-C6H4SO2NH2) and NaCl, which are reduction products. The chloramine-T redox potential is According to the medium's PH, the p-TSA redox couple [32, 33] changes 0.778 V at pH 7.0, 0.614 Vat pH 9.7, and 1.139 V at pH 0.65. The aqueous solution of CAT exhibits significant electrolyte properties. Depending on the pH value, chloramine-T generates various reactive species [34]. RNCl2 (dichloramine-T), HOCl, and RNHCl are examples of potential oxidizing species of chloramine-T in acidic solution. Based on CAT, the rate law predicts a second-order dependent if RNCl2 a reactive species, which is at contrasts with the actual results. Chloramine-T reactions in solutions include the presence of polar molecules and ions. It has been found that when the proportions of the solvent components change,
the reaction rate will change and that the relationship between the log k versus 1/D will give a straight line with a positive slope, meaning the participation of a positive ion with a dipole molecule in the rate determining step of the reaction. It has been observed that the reaction rate does not change when the ionic strength of the solution increases when different concentrations of sodium perchlorate are added. This indicator confirms the participation of a positive ion and a dipole molecule. It has been shown from the values of the reaction rate constants in Table 5 when the chloramine-T oxidizing agent reacts with N- benzoyl valine, the existence of two possibilities for the reaction will be expected [35].
The first possibility is that the active part of the chloramine-T is the positive ion, which is represented by (Cl+, H2OCl+), while n-benzoyl amino acids will be a dipole molecule (Scheme
I):
ki
RNC1 + H+ „ , " RNHCl.......fast
kl
RNHCl + H20 - 2 - HOCl + RNH2.......slow
k-2
HOCl + N-B-V-^-^ B-V-Cl + H20.......fast
Scheme I.
As for the second possibility, the active part of Chloramine-T is the positive ion which is represented by H2OCl+ as a dipolar molecule
with positive ion of n-benzoyl valine (Scheme II):
ki
RNC1 + H+ ^ , " RNHC1.......fast
kl
RNHC1 + H20 ^ 2 " HOC1 + RNH2.......fast
k-2
HOC1 + H+ k3 » H2OCl+..........slow determining step
H2OCl+ + N-B-V k4 » B-V-Cl + H20.......fast
Scheme II.
Causes the gradual formation of HOCI 3), which interacts quickly with a substrate. through the hydrolysis of RNHCl. Rapid Using the steady state estimate in relation
reaction with N-benzoyl valine comes next to HOCl and CAT, the following equation is (Scheme I, step 3). Alternatively, it can undergo obtained: protonation to produce H2OCl+ (Scheme II, step
= TSfavww+i (5)
this equation becomes -d
[CAT] = [CAT] = K = [CAT] [H+] (6)
Where:
„ KiK2[H20] ^ ^
K = — = constant
K-1+K2[H20]
Derivatization rates Law - equation (6) is Scheme III provides the CAT's mechanism for complete based on experimental Kinetic study. oxidizing n-benzoyl valine [36]:
O O
o o
Ph-C-N-C-C-OH + CI-OC© -.Ph-C-N-Ç-C-OH +H20 + H+
I \t I I
^ H Cl R
Scheme III.
This Scheme involves the removal of the provided n-chloro-acetyl Valine (the product) after an electrophilic attack by the partly cationic chlorine of H2OQ+ on the nitrogen atom of N-benzoyl Valine.
The first order constant somewhat
decreased when the initial chloramine-T concentration increased (Table 1), possibly as a result of deactivation carried on by the creation of small quantities [37] of NaClO3 in side reaction giving further evidence that HOCl, H2OO+ is of reactive type:
HOCl + Na ^ NaOCl + H+ (7)
or H2OCl++ Na ^ NaOCl + 2H+ (8)
3NaOCl ^ NaCl + 2NaO (9)
Lastly, the substantial negative value of supported by the proposed mechanism. the activation entropy, which denotes the Furthermore, the activator complex is more production of a rigid transition state, is ordered than the reactant.
Conclusion
1. The rate of decrease in the concentration of chloramine_T per unit of time follows a first-order equation, as it was found that the rate of the oxidation of reaction depends on the concentration of chloramine_T and the hydrochloric acid.
2. When changing the ionic intensity by adding different concentrations of sodium perchlorate, it was found that the rate of the reaction rate is not affected by this change.
3. The rate constant of the oxidation reaction
of N-benzoyl valine was slightly affected when different concentrations of the reaction product para toloune sulfonamate were added.
4. It was found that when the percentage of ethanol and water in the solvent increases, the rate of the reaction increases, i.e. in other words, the rate of the reaction increases with a decrease in the dielectric constant of the solvent.
References
1. Singh A.K., Negi R., Jain B., Katre Y., Singh S.P., Sharma V.K. Pd (II) catalyzed oxidative degradation of paracetamol by chloramine-T in acidic and alkaline media. Industrial & engineering chemistry research, 2011, Vol. 50(14), p. 8407-8419.
2. Filler R. Oxidations and Dehydrogenations with N-Bromosuccinimide and Related N-Haloimides. Chemical Reviews, 1963, Vol. 63(1), p. 21-43.
3. Campbell M.M., Johnson G. Chloramine T and related N-halogeno-N-metallo reagents. Chemical Reviews, 1978, Vol. 78(1), p. 65-79.
4. Meena W., Shubha J. Kinetic study of Oxidation of some Monosaccharides by chloramine-T induced by Visible light source. Research Journal of Chemical Sciences, 2014, Vol. 4(7), p. 61-65.
5. Verma A., Pandey J., Srivastava S. Iridium (III) catalyzed oxidation of leucine by Chloramine-T in acidic medium: A kinetic and mechanistic study. Proceedings of the National Academy of Sciences, India Section A: Physical Sciences, 2017, Vol. 87(1), p. 163-170.
6. Verma A., Pandey J., Srivastava S. Kinetic and mechanistic study of oxidation of l-alanine by an acidic solution of chloramine-T in the presence of chloro-complex of Ir (III) as a homogeneous catalyst. Can Chem Trans, 2016, Vol. 4, p. 1-16.
7. Pandey J., Verma A., Patel R., Srivastava S. Kinetic, mechanistic, and thermodynamic investigations on Iridium (III) catalyzed oxidation of D-Mannitol by N-chloro-p-
toluenesulfonamide in perchloric acid medium. Iranian Journal of Chemical Engineering, 2017, Vol. 14(4), p. 77-89.
8. Srivastava S., Singh P. Pd (II) catalysis in the oxidation of D-Glucose by chloramine-T in acidic medium: A kinetic study. J. Oxidation Communication Book, 2008, Vol. 4(31), p.853-859.
9. Shivananda K.N., Jagadeesh R.V., Mahendra K.N. Ru (III)-catalyzed oxidation of some amines by chloramine-T in hydrochloric acid medium: Mechanistic aspects and kinetic modeling. Journal of Molecular Catalysis A: Chemical, 2006, Vol. 255(1-2), p.159-170.
10. Shubha J.P. Oxidative conversion of thiourea and N-substituted thioureas into formamidine disulfides with acidified chloramine-T: a kinetic and mechanistic approach. Journal of Sulfur Chemistry, 2009, Vol. 30(5), p.490-499.
11. Zhang T., Gunten U. Chlorination of amides: Kinetics and mechanisms of formation of N-chloramides and their reactions with phenolic compounds. Water Research, 2023, Vol. 242, p.120-131.
12. Veena M.S., Prashanth M.K., Yogesh K., Muralidhara H.B., Arthoba N.Y. Kinetics and mechanistic study of oxidation of amoxicillin by chloramine-T in acid medium. Journal of the Chilean Chemical Society, 2015, Vol. 60(3), p. 3063-3068.
13. Sharma P., Sailani R., Meena A., Khandelwal C.L. Oxidation of crotyl alcohol by N-chloro-4-methylbenzene sulphonamide in acidic medium and alkaline media in the presence of os (VIII) catalyst-a kinetic
pathway. Turkish Journal of
Chemistry, 2020, Vol. 44(4), p. 950-970.
14. Saeed N.H.M., Abbas A.M. Kinetics and mechanism of tetrahydrofuran oxidation by chloramine_T in acidic media. Periodico Tche Quimica, 2020, Vol. 17(35), p.449-461.
15. Hassan Y.I., Saeed N.H.M. Kinetics and mechanism of oxidation of diethyl ether by chloramine-T in acidic medium. Journal of Chemistry, 2012, Vol. 9, p. 642-649.
16. Saeed N.H. Kinetics and Mechanism of Chlorination of N-Acetylglycin by Chloramine-T In Acidic Medium. Journal of education and science, 2010, Vol. 24(3), p. 1-50.
17. Yaseen M.H., Elwahab G.H.A., Saeed N.H. Oxidation of n-acetyl alanine by chloramine-t in the presence of hydrochloric acid: a kinetic and mechanistic study. Central Asian Journal of Medical and Natural Science, 2024, Vol. 5(1), p. 205214.
18. Sadeek G.T., Saeed Z.F., Saleh M.Y. Synthesis and pharmacological profile of hydrazide compounds. Research Journal of Pharmacy and Technology, 2023, Vol. 16(2), p. 975-982.
19. Munavalli D.S., Chimatadar S.A., Nandibewoor S.T.A kinetic and mechanistic study of oxidation of l-lysine by the analytical reagent diperiodatoargentate (III) in aqueous alkaline medium. Transition Metal Chemistry, 2008, Vol. 33, p.535-542.
20. Brian S.F., Antony J.H., Peter G.S., Austin R.T. Vogels Text Book of particle Organic Chemistry, 5 th ed. Longman, London, U. K. 1989, p. 1540.
21. Morries J.C., Salazar J.A., Wineman M.A. Equilibrium Studies on N-Chloro Compounds. I. The Ionization Constant of N-Chloro-p-toluenesulfonamide. Journal of the American Chemical Society. 1948, Vol. 70(6), p. 2037-2041.
22. Fatah S.A., Amhimmid W.K. Synthesis and Chemical Reaction of 2-Oxazoline 5-Ones Derivatives. International Journal of Chemical and Biomolecular Science. 2019, Vol. 5(1), p. 7-18.
23. Saleh M.Y., Aldulaimi A.K.O., Saeed S.M., Adhab AH. TiFe2O4@ SiO2-SOsH: A
novel and effective catalyst for esterification reaction. Heliyon. 2024, Vol. 10, p. 1-10.
24. Majhool A.A., Saleh M.Y., Aldulaimi A.K.O., Saeed S.M., Hassan S.M., El-Shehry M.F., Azziz S.S. Synthesis of New Azo Dyes of Uracil via Ecofriendly Method and Evaluation For The Breast, Liver and Lung Cancer Cells In vitro. Chem. Rev. Lett, 2023, Vol. 6(10), p. 220-234.
25. Broekaert J.A., Daniel C.H. Quantitative chemical analysis. W.H Freeman and Company. New York. 2015, p. 644.
26. Zalov A.Z., Iskenderova K.O., Askerova Z.G., Hajiyeva A.B. Spectrophotometric study of nickel (II) complexes with 2-hydroxythiolphenol and its derivatives in the presence of hydrophobic amine. Chemical Problems, 2021, Vol. 19(4), p. 224-231.
27. Hassan Y.I., Saeed N.H. Kinetic study of chlorination of p-methoxyacetanilide by chloramine-T in hydrochloric acid medium. Oriental Journal of Chemistry, 2010, Vol. 26(2), p. 415-420.
28. Hamdoon A.M., Saleh M.Y. Synthesis and biological evaluation of novel series of benzo [f] indazole derivatives. Egyptian Journal of Chemistry, 2022. Vol. 65(11), p. 305-312.
29. Jain S., Bakhru M., Nagwanshi R. A kinetic study of photochemical oxidation of sucrose by chloramine-T in acidic medium. Journal of the Indian Chemical Society, 2011, Vol. 88(7), p. 963-971.
30. Saleh A., Saleh M.Y. Synthesis of heterocyclic compounds by cyclization of Schiff bases prepared from capric acid hydrazide and study of biological activity. Egyptian Journal of Chemistry, 2022, Vol. 65(12), p. 783-792.
31. Jouyban A., Soltanpour S., Chan H.K.A simple relationship between the dielectric constant of mixed solvents with solvent composition and temperature. International journal of pharmaceutics, 2004, Vol. 269(2), p. 353-360.
32. Saied S.M., Saleh M.Y., Hamdoon A.M. Multicomponent synthesis of Tetrahydrobenzo [a] xanthene and Tetrahydrobenzo [a] acridine derivatives using Sulfonated Multi-Walled Carbon Nanotubes as Heterogeneous
Nanocatalysts. Iranian Journal of Catalysis, 2022, Vol. 12(2), p. 189-205.
33. Campbell M.M., Johnson G. Chloramine T and related N-halogeno-N-metallo reagents. Chemical Reviews, 1978, Vol. 78(1), p. 65-79.
34. Singh A.K., Negi R., Jain B., Katre Y., Singh S.P., Sharma V.K. Pd (II) catalyzed oxidative degradation of paracetamol by chloramine-T in acidic and alkaline media. Industrial & engineering chemistry research, 2011, Vol. 50(14), p. 8407-8419.
35. Bishop E., Jennings V.J. Titrimetric analysis with chloramine-T—IV: The chloramine-T-
iodide reaction. Talanta, 1961, Vol. 8(10), p. 697-704.
36. Ali A.H., Saleh M.Y., Owaid K.A. Mild Synthesis, Characterization, and Application of some Polythioester Polymers Catalyzed by Cetrimide Ionic Liquid as a Green and Eco-Friendly Phase-Transfer Catalyst. Iran. J. Catal, 2023, Vol. 13, p. 73-83.
37. Mushran S.P., Agrawal M.C., Prasad B. Mechanism of oxidations by chloramine-T. Part I. Oxidation of a-hydroxy-acids. Journal of the Chemical Society B: Physical Organic, 1971, Vol. 130(11), p. 1712-1714.
