USE IN PHARMACEUTICAL ANALYSIS OF IONIC ASSOCIATION COMPLEXES FORMED BETWEEN SULPHONEPHTHALEIN DYES AND NITROGEN -CONTAINING COMPOUNDS IN MEDIUM OF ORGANIC SOLVENTS

Authors

DOI:

https://doi.org/10.15421/jchemtech.v31i4.284764

Keywords:

ion association complex; sulfonephtalein dyes; pharmaceutical analysis; spectrophotometry; tautomerism

Abstract

The review systematizes and discusses data on the new class of reactions based on the formation of ionic association complexes (IAS) between sulfonephtalein dyes (SPD) and basic nitrogen containing organic substances (NOS) taking place in organic solvent. The mechanism of formation of IA, the influence of the nature of organic solvent on the IA formation and the chemical analytical characteristics of the developed methods of analysis are discussed. The reaction mechanism includes the displacement of a tautomeric equilibrium from a colorless lactonic tautomer to an intensively colored yellow quinonoid form, which is due to the formation of IA between the monoanionic form of the SPD and the protonated form of the NOS. The reaction goes better in the environment of polar organic solvents. Chloroform, dichloromethane and acetone are most often used. The formation of IA in most cases occurs very quickly. A large concentration of SPD about 0.01 - 0.1% is required to completely displace equilibrium towards IA. The molar absoprtivity coefficients are high and reach (30–40)×103 mol-1 l cm-1. The main advantages of new analytical forms are simplicity, speed, lack of complex and lengthy stage of the separation, the possibility of automation. IAs formed between SPD and NOS in organic solvent are attractive and promising forms for use in pharmaceutical analysis.

 

References

Georgiyevsky, V. P. (Ed.). (2011). [Analytical Chemistry in the Development, Standardization and Quality Control of Medications.] Kharkov, Ukraine: «HTMT». (in Russian)

Florea, M., Ilie, M. (2017). Ion-pair spectrophotometry in pharmeceutical and biomedical analysis: Challenges and perspectives. In book: Spectroscopic Analyses - Developments and Applications. Ed. Sharmin, E., Zafar, F., 173–192. http://dx.doi.org/10.5772/intechopen.69778

Rahman, N., Khan, N. A., Azmi, S. N. H. (2004). Extractive spectrophotometric methods for the determination of nifedipine in pharmaceutical formulations using bromocresol green, bromophenol blue, bromothymol blue and eriochrome black T. Il Farmaco, 59, 47–54. https://doi.org/10.1016/j.farmac.2003.10.001

Hedjazi, M., Vishnikin, A. B., Okovytyy, S. I., Miekh, Yu. V., Bazel, Ya. R. (2022). Use of dye aggregation phenomenon for spectrophotometric and SIA-LAV determination of bismuth(III) as a specific ion association complex between tetraiodbismuthate and Astra Phloxine. J. Molec. Struct., 1251, 132015. https://doi.org/10.1016/j.molstruc.2021.132015

Hedjazi, M., Vishnikin, A. B., Khudyakova, S. N. (2019). Rapid, highly sensitive and selective spectrophotometric determination of cadmium(II) as an ion associate of tetraiodocadmiate(II) with Astra Phloxine. J. Chem. Technologies, 27, 293–303. https://doi.org/10.15421/081930

Vishnikin, A. B., Al-Shwaiyat, M. K. E. A., Bazel, Y. R., Andruch, V. (2007). Rapid, sensitive and selective spectrophotometric determination of phosphate as an ion associate of 12-molybdophosphate with Astra Phloxine. Microchim. Acta, 159, 371–378. https://doi.org/10.1007/s00604-007-0754-7

Hedjazi, M., Vishnikin, A. B., Balanenko, A. D. (2021). A green spectrophotometric method for determination of drotaverine hydrochloride in pharmaceutical preparations using formation of ion association complex with erythrosine. J. Chem. Technologies, 29(3), 467–475. https://doi.org/10.15421/jchemtech.v29i3.242348

El-Ansary, A. L., Issa, Y. M., Selim, W. (1999). Spectrophotometric determination of trimethoprim in pure form and in pharmaceutical preparations using Bromothymol Blue, Bromocresol Green and Alizarin Red S. Anal. Lett., 32, 955–969. https://doi.org/10.1080/00032719908542869

Shahdousti, P., Aghamohammadi, M., Alizadeh, N. (2008). Spectrophotometric study of the charge-transfer and ion-pair complexation of methamphetamine with some acceptors. Spectrochim. Acta A, 69, 1195–1200. https://doi.org/10.1016/j.saa.2007.06.035

Zahorodniy, S. L., Vasyuk, S. O. (2013). [Spectrophotometric determination of dimedrole in tablets]. Current issues in pharmacy and medicine: science and practice, (2) (12), 98–101 (in Ukrainian). https://doi.org/10.14739/2409-2932.2014.2.26128

Burlaka, J. V., Tarkhanova, O. O., Vasjuk, S. O., Keytlin, I. V. (2010). [Determination of flukonazole in pharmaceutical preparations with Bromthymol Blue]. Farmatsevtychnyi zhurnal, (3), 69–75 (in Ukrainian). https://pharmj.org.ua/index.php/journal/article/view/803/757

Prashanth, K. N., Basavaiah, K. (2012). Simple, sensitive and selective spectrophotometric methods for the determination of atenolol in pharmaceuticals through charge transfer complex formation reaction. Acta Pol. Pharm., 69(2), 213–223.

Mchedlov-Petrossyan, N. O., Kukhtik, V. I., Bezugliy, V.D. (2003). Dissociation, tautomerism and electroreduction of xanthene and sulfonephthalein dyes in N,N-dimethylformamide and other solvents. J. Phys. Org. Chem., 16, 380–397. https://doi.org/10.1002/poc.654

Mchedlov-Petrossyan, N. O., Surov, Yu. N., Trofimov, V. A., Tsivadze, A. Yu. (1991). Vibrational spectra of certain triphenylmethane dyes and their structure in solution. Theor. Exp. Chem., 26(6), 644–653. https://doi.org/10.1007/BF00536430

Prashanth, K. N., Basavaiah, K., Raghu, M. S. (2012). Rapid and Sensitive Spectrophotometric Measurement of Non-Specific Beta Blocker Propranolol Hydrochloride Using Three Sulphonphthalein Dyes In Pure Form, Pharmaceuticals and Human Urine. Chem, Sci J., 3, CSJ-80.

Gainza, A. H. (1987). Associations of ajmaline and homatropine with bromocresol green and bromophenol blue in dichloromethane: thermodynamic and kinetic parameters. Can. J. Chem., 65, 1279–1291. https://doi.org/10.1139/v87-215

Prashanth, K. N., Basavaiah, K., Vinay, K. B. (2016). Sensitive and selective spectrophotometric assay of rizatriptan benzoate in pharmaceuticals using three sulphonphthalein dyes. Arabian J. Chem., 9, 971–980. https://doi.org/10.1016/j.arabjc.2011.10.006.

Sulyma, M. I., Ogurtsov, V. V., Zhuk, Yu. M., Vasyuk, S. O., Khomyak, S. V. (2018). [Study the structure of diltiazem and bromocresol green reaction product]. Pharmaceutical Review, (3), 58–63 (in Ukrainian). https://doi.org/10.11603/2312-0967.2018.3.9316

Shulyak, N., Protsyk, S., Kucher, T., Kryskiw, L. (2022). Development of the spectrophotometric method for the determination of atorvastatin in tablets by using Bromothymol Blue. ScienceRise: Pharm, Sci,, (4) (38), 89–97. https://doi.org/10.15587/2519-4852.2022.263878

Shulyak, N., Protsyk, S., Kucher, T., Kryskiw, L., Poliak, O., Mosula, L., Logoyda, L. (2022). Development of the spectrophotometric method for the determination of atorvastatin calcium in tablets by using Bromophenol Blue. Methods Objects Chem. Anal., 17(3), 111–117. https://doi.org/10.17721/moca.2022.111-117

Horyn, M., Kryskiw, L., Kucher, T., Poliak, O., Zarivna, N., Zahrychuk, H., Korobko, D., Peleshok, K., Logoyda, L. (2022a). Development of the spectrophotometric method for the determination of metoprolol in tablets by using bromophenol blue. ScienceRise: Pharm. Sci., (6) (40), 29–35. https://doi.org/10.15587/2519-4852.2022.270311

[22] Horyn, M., Kucher, T., Kryskiw, L., Poliak, O., Zarivna, N., Peleshok, K., Logoyda, L. (2022b). Development of the spectrophotometric method for the determination of metoprolol tartrate in tablets by using bromocresol green. ScienceRise: Pharm. Sci., (4) (38), 55–63. https://doi.org/10.15587/2519-4852.2022.266068

Halka, L., Kucher, T., Kryskiw, L., Piponski, M., Furdela, I., Uglyar, T., Poliak, O., Logoyda, L. (2023). Development of the spectrophotometric method for the determination of rosuvastatin in tablets by using bromophenol blue. ScienceRise: Pharm. Sci., 2(42), 11–19. http://doi.org/10.15587/2519-4852.2023.277461

Niranjani, S., Venkatalacham, K. (2019). Spectrophotometric determination of atorvastatin calcium and pitavastatin calcium through ion-pair complex formation using acid dyes in pharmaceutical formulations and human urine samples. Int. J. Appl. Pharm., 11(6), 171–180. https://doi.org/10.22159/ijap.2019v11i6.35246

Prashanth, K. N., Basavaiah, K. (2018). Modified extraction-free ion-pair methods for the determination of flunarizine dihydrochloride in bulk drug, tablets, and human urine. J. Appl. Spectr., 84(6), 1114–1123. https://doi.org/10.1007/s10812-018-0596-6

Ivanitsa, L. O., Chernyavskaya, A. Y., Zabolotna, N. I., Vishnikin, A. B. (2018). Spectrophotometric determination of polyacrylamide type flocculants, Methods Objects Chem. Anal., 13, 5–12. https://doi.org/10.17721/moca.2018.5-12

Chernyavskaya, A. Y., Vishnikin, A. B., Ivanitsa, L. O. (2018). [Investigation of interaction of bromphenol blue with cationic polyacrylamides and application of it in analysis]. Odesa National University Herald. Chemistry, 23(1), 36–47 (in Russian).

Savvin, S. B., Chernova, R. K., Shtykov, S. N. (1991). [Surface active substances]. M., Nauka. (in Russian)

Peleshok, K., Bondar, B., Kryskiw, L., Kucher, T., Poliak, O., Logoyda, L. (2021). Non-extractive spectrophotometric determination of valsartan in pure form and in pharmaceutical products by ion-pair complex formation with bromophenol blue and methyl red. Pharmacia, 68(4), 851–858. https://doi.org/10.3897/pharmacia.68.e73559

Deepakumari, H. N., Mallegowda, S. M., Vinay, K. B., Revanassiddappa, H. D. (2013). Simple and extraction-free spectrophotometric methods for risperidone in pure form and in dosage forms. Chem. Ind. Chem. Eng. Quarterly, 19, 121–128. https://doi.org/10.2298/CICEQ110824046D

Swamy, N., Basavaiah, K. (2013). Use of two sulfonphthalein dyes for the sensitive and selective extraction-free spectrophotometric assay of albendazole in bulk drug and in tablets. ISRN Anal. Chem., (3), 734027. https://doi.org/10.1155/2013/734027

Rajendraprasad, N., Basavaiah, K., Vinay, K. (2010). Sensitive and selective extraction-free spectrophotometric determination of quetiapine fumarate in pharmaceuticals using two sulphonthalein dyes. J. Pre-Clin. Clin. Res., 4(1), 24–31.

Abdulrahman, S. A. M., Basavaiah, K. (2012). Spectrophotometric determination of dothiepin hydrochloride in pharmaceuticals through ion-pair complexation reaction. Chem. Ind. Chem. Eng. Quarterly, 18, 339–347. https://doi.org/10.2298/CICEQ111009010A

Zenita, O., Basavaiah, K., Vinay, K. B. (2011). Sensitive and selective extraction free ion-pair complexometric determination of domperidone in pharmaceuticals and in spiked human urine. J. Chil. Chem. Soc. 56(2), 715–720. http://dx.doi.org/10.4067/S0717-97072011000200021

Swamy, N., Basavaiah, K., Vinay, K. B. (2014), Extraction-Free Spectrophotometric Determination of Pyrantel Pamoate in Pharmaceuticals. Proc. Indian Natn, Sci. Acad., 80(3), 597–608. https://doi.org/10.16943/ptinsa/2014/v80i3/47913

Zhuk, Y. N., Vasyuk, S. A. (2014). [Spectrophotometric determination of metoprolol tartrate in tablets]. Vestnik Pharmacii, 2(64) 64–70 (in Russian).

Abdine, H., Belal, F., Zoman, N. (2002). Simple spectrophotometric determination of cinnarizine in its dosage forms. Il Farmaco, 57, 267–271. https://doi.org/10.1016/S0014-827X(02)01204-1

El-Yazbi, F. A., Gazy, A. A., Mahgoub, H., El-Sayed, M. A., Youssef, M. (2003). Spectrophotometric and titrimetric determination of nizatidine in capsules. J. Pharm. Biomed. Anal., 31, 1027–1034. https://doi.org/10.1016/S0731-7085(02)00699-4

El-Kerdawy, M. A., Moustafa, M. A., El-Ashry, S. M., El-Wasf, D. R. (1993). Spectrophotometric determination of certain phenothiazines and their dosage forms using Bromophenol Blue. Anal. Lett., 26, 1669–1680. https://doi.org/10.1080/00032719308021488

Vinay, K. B., Revanassiddappa, H. D., Rajendraprasad, N., Ramesh, P. J., Xavier, C. M., Basavaiah, K. (2012). Use of two sulfonthalein dyes in the extraction-free spectrophotometric assay of tramadol in dosage forms and in spiked human urine based on ion-pair reaction. Drug Testing and Analysis, 4(2), 116–122. https://doi.org/10.1002/dta.247

El-Ansary, A. L., Abdel-Kader, N. S., Asran, A. M. (2018). Spectrophotometric studies on the reaction of diaveridine with some sulfonphthalein dyes based on ion-pair/ion-associate complexes formation. J. Spectroscopy, 9269148. https://doi.org/10.1155/2018/9269148

Basavaiah, K., Abdulrahman, S. A. M., Vinay, K. B. (2009). Simple and sensitive spectrophotometric determination of olanzapine in pharmaceutical formulations using two sulphonphthalein acid dyes. J. Food Drug Anal., 17(6), 434–442. https://doi.org/10.38212/2224-6614.2585

[Zhuk, Y. N., Vasyuk, S. O. (2016), Spectrophotometric determination of betaxolol in pure form and pharmaceuticals. Pharma Innovation, 5(6), 31–33.

[44] Ramesh, P. J., Basavaiah, K., Zenita Devi, O., Vinay, K.B. (2010). Simple and sensitive spectrophotometric assay of ofloxacin in pharmaceuticals based on ion-pair reaction. Chem. Ind. Chem. Eng. Quarterly, 16, 353–362. https://doi.org/10.2298/CICEQ100328037R

[45] Zhuk, Yu. M., Vasiuk, S. O., Keytlin, I. V. (2012). [Spectrophotometric determination of bisoprolol with Thymol Blue]. Zaporozhye Medical Journal. 14(3), 62–64 (in Ukrainian).

Zhuk, Y. M., Vasyuk, S. O. (2016). [Spectrophotometric determination of sotalol in tablets]. Farmatsevtychnyi zhurnal, (1), 49–55 (in Ukrainian). https://pharmj.org.ua/index.php/journal/article/view/150/82

Sulyma, M. I., Ogurtsov, V. V., Zhuk, Yu. M., Vasyuk, S. O. (2017). [Method development and validation of diltiazem in pharmaceutical forms by spectrophotometric quantitative determination]. Pharmaceutical Review, (2), 57–62 (in Ukrainian). https://doi.org/10.11603/2312-0967.2017.4.8340

Burlaka, J. V., Tarkhanova, O. O., Korzhova, A. S., Vasjuk, S. O., Keytlin, I. V. (2011). [Spectrophotometric determination of terbinafine in tablets based on the reaction with bromocresole green]. Farmatsevtychnyi zhurnal, (2), 66–70 (in Ukrainian). https://pharmj.org.ua/index.php/journal/article/view/680/639

Burlaka, J. V., Tarkhanova, O. O., Vasjuk, S. O., Keytlin, I. V. (2010). [Spectrophotometric determination of clotrymazole in pharmaceutical compositions]. Zaporozhye Medical Journal. 12(4), 63–66 (in Ukrainian).

Zahorodniy, S. L., Vasyuk, S. O. (2014). [Spectrophotometric determination of trihehylphenidyl in tablets]. Pharmaceutical Review, (4), 58–63. (in Ukrainian). https://doi.org/10.11603/2312-0967.2014.4.3454

Zhuk, Yu. M., Vasiuk, S. O., Verovkina, I. S. (2015), [Spectrophotometric determination of carvedilol in tablets]. Pharmaceutical Review, (3), 24–28 (in Ukrainian). https://doi.org/10.11603/2312-0967.2015.3.4928

Sulyma, M. I., Ogurtsov, V. V., Zhuk, Yu. M., Vasyuk, S. O. (2018). [Method validation of verapamil hydrochloride in pharmaceutical forms by spectrophotometric quantitative determination]. Pharmaceutical Review, (2), 65–70. (in Ukrainian). https://doi.org/10.11603/2312-0967.2018.2.9085

Sulyma, M. (2018), Spectrophotometric determination of verapamil hydrochloride using Bromokresol Green. Der Pharma Chemica, 10(5), 143–147.

Burlaka, J. V., Tarkhanova, O. O., Vasjuk, S. O. (2009). [Spectrophotometric determination of ceftriaxone]. Zaporozhye Medical Journal. 11(6), 93–94 (in Ukrainian).

Burlaka, J. V., Portna, K. V., Tarkhanova, O. O., Vasjuk, S. O. (2010). [Spectrophotometric determination of some cephalosporins with Cresol Red]. Current issues in pharmacy and medicine: science and practice, (4) (23), 17–19 (in Ukrainian).

Zahorodniy, S. L., Vasyuk, S. O. (2014). [Quantitative determination of zopiclone in tablets «Sonovan» by spectrophotometry]. Current issues in pharmacy and medicine: science and practice, (2) (15), 23–26 (in Ukrainian). https://doi.org/10.14739/2409-2932.2014.2.26128

Vinay, K. B., Revanasiddappa, H. D., Rajendraprasad, N., Basavaiah, K. (2011). Sensitive, selective and extraction-free spectrophotometric determination of lamotrigine in pharmaceuticals using two sulphonthalein dyes. Thai. J. Pharm. Sci. 35, 65–76.

Basavaiah, K., Zenita, O. (2011). Spectrophotometric determination of famotidine using sulphonphthalein dyes. Quim. Nova, 34(5), 735–742. https://doi.org/10.1590/S0100-40422011000500002

Qarah, N. A. S., Basavaiah, K. (2018). Extraction-free spectrophotometric assay of ethionamide in pharmaceutical using two sulphonphthalein dyes as ion-pair agents. Proc. Indian Natn, Sci. Acad., 88(4), 499–506. https://doi.org/10.1007/s40010-017-0467-1

Raghu, M. S., Basavaiah, K. (2012). Rapid and sensitive extraction-free spectrophotometric methods for the determination of pheniramine maleate using three sulphonthalein dyes. Proc. Indian Natn, Sci. Acad., 82(3), 187–196. https://doi.org/10.1007/s40010-012-0019-7

Cardoso, S. G., Leggli, C. V. S., Pomblum, S. C. G. (2007). Spectrophotometric determination of carvedilol in pharmaceutical formulations through charge-transferand ion-pair complexation reactions. Pharmazie, 62(1), 34–37. https://doi.org/10.1691/ph.2007.1.6075

[62] Ramachandran, S., Mandal, B. K., Navalgund, S. G. (2011). Simultaneous Spectrophotometric determination of valsartan and ezetimibe in pharmaceuticals. Tropical J. Pharm, Res. 10(6), 809–815. https://doi.org/10.4314/tjpr.v10i6.15

Al-Ghannam, S. M. (2006). A simple spectrophoto-metric method for the determination of β-blockers in dosage forms. J. Pharm. Biomed. Anal., 40, 151–156. https://doi.org/10.1016/j.jpba.2001.12.001

Zagorodniy, S. L., Monaykina, Y. V., Vasyuk, S. O. Quantitative determination of ketotifen in drug dosage forms by spectrophotometric method. Int. J. Adv. Pharm. Biol. Chem., 4(2), 373–377.

Manjunatha, D. H., Shaikh, S. M. T., Harikrishna, K., Sudhirkumar, R., Kandagal, P. B., Seetharamappa, J. (2008), Simple and sensitive spectrophotometric methods for the determination of acebutolol hydrochloride in bulk sample and pharmaceutical preparations. Ecl. Quím., 33(2), 37–40. https://doi.org/10.1590/S0100-46702008000200005

Shalaby, A., El-Maamly. M., Abdel-Gawad, F. M., Azab, S. M., Eldin, A. S. (2017). Spectrophotometric determination of daclatasvir dihydrochloride by ion-pair reaction with Bromophenol Blue, Bromothymol Blue and Bromocresol Green. Chem. Res. J., 2, (6), 163–173. https://chemrj.org/download/vol-2-iss-6-2017/chemrj-2017-02-06-163-173.pdf

Omar, M. A., Abdelmageed, O. H., Abdel-Gaber, A. A., Abdel-Megied, A. M. (2011). Spectrophotometric and spectrofluorimetric determination of certain angiotensin receptor blockers through complex formation. J. Pharm. Sci. Res., 3(10), 1499–1510.

Nagib Qarah, A. S., Basavaiah, K., Swamy, N. (2017). Sensitive and selective extraction-free spectrophotometric assay of chloroquine phosphate in pharmaceuticals based on ion-pair reaction with Bromocresol Green and Bromocresol Purple. Pharm. Anal. Acta, 8(3) 539. https://doi.org/10.4172/2153-2435.1000539

Prashanth, K. N., Swamy, N., Basavaiah, K. (2014). Extraction-free ion-pair methods for the assay of trifluoperazine dihydrochloride in bulk drug, tablets, and spiked human urine using three sulfonphthalein dyes. J. Appl. Spectr., 81(5), 893–902. https://doi.org/10.1007/s10812-014-0024-5

El-Ashry, S. A., Aly, F. A., El-Brashy, A. M. (1994). Studies of complex formation between the bromophenol blue and some important aminoquinoline antimalarials. Arch. Pharm. Res., 17(6), 415–419. https://doi.org/10.1007/BF02979117

Sydorova, L., Bokhan, Yu., Kormosh, Zh., Plonsak, P., Pavlenko Yu. (2020) Simultaneous determination of the content of synthetic dyes Е110 and Е124 in the mixture. Forensic Bulletin, 33(1), 81–93. https://doi.org/10.37025/1992-4437/2020-33-1-81

Sidorova, L. P., Vishnikin, A. B., Voloboy, A. O. (2019). Simultaneous spectrophotometric determination of food dyes in binary mixtures by H-point standard addition method. J. Chem. Technologies, 27(2), 276–284. https://doi.org/10.15421/081928

Sidorova, L. P., Vishnikin, A. B., Sidorova, M. G(2022). Simultaneous determination of synthetic food dyes in binary mixtures by Mean centering and Ratio difference methods. J. Chem. Technologies, 30(2), 298–306. https://doi.org/10.15421/jchemtech.v30i2.259255

Vishnikin, A. B., Sklenařova, H., Solich, P., Petrushina, G. A., Tsiganok, L. P. (2011). Determination of ascorbic acid with Wells-Dawson type molybdophosphate in sequential injection system. Anal. Lett., 44(1-3), 514–527. https://doi.org/10.1080/00032719.2010.500789

Vishnikin, A. B., Al-Shwaiyat, M. K. E. A., Petrushina, G. A., Tsiganok, L. P., Andruch, V., Bazel, Ya. R., Sklenarova, H., Solich, P. (2012). Highly sensitive sequential injection determination of p-aminophenol in paracetamol formulations with 18-molybdodiphosphate heteropoly anion based on elimination of Schlieren effect. Talanta, 96, 230–235. https://doi.org/10.1016/j.talanta.2012.02.049

Vishnikin, A. B., Svinarenko, T. Ye., Sklenářová, H., Solich, P., Bazel, Ya. R., Andruch, V. (2010). 11-Molybdobismuthophosphate – a new reagent for the determination of ascorbic acid in batch and sequential injection systems. Talanta, 80, 1838–1845. https://doi.org/10.1016/j.talanta.2009.10.031

Vishnikin, A., Hedjazi, M., Al-Shwaiyat, M., Skok, A., Bazel, Y. (2023). Consecutive spectrophotometric determination of phosphate and silicate in a sequential injection lab-at-valve flow system. Anal. Chim. Acta, 1273, 341464. https://doi.org/10.1016/j.aca.2023.341464

Published

2024-01-26