The chromatographic characteristics are investigated for eight aromatic derivatives of 3-chloro-1,4-naphthoquinone under conditions of normal-phase thin-layer chromatography for benzene-based binary mobile phase and such polar solvents as chloroform, acetone, acetonitrile, methanol and propan-2-ol. The slope of linear retention dependencies for the investigated compounds on the concentration of the polar component in the mobile phase satisfactorily correlates with the area occupied by the adsorbed analyte molecule in the stationary phase. The intercept in the Soczewinski equation depends on the polar component of the mobile phase.
1. Bechtold T. (2010). Handbook of natural colorants. Chichester: Wiley.
https://doi.org/10.1002/9780470744970
2. Ibis Cemil, Tuyun Amac Fatih, Bahar Hakan, Ayla Sibel Sahinler, Stasevych Maryna V., Musyanovych Rostyslav … Novikov Volodymyr (2013). Synthesis of novel 1,4-naphthoquinone derivatives: antibacterial and antifungal agents. Medicinal Chemistry Research, 22(6), 2879-2888. doi:10.1007/s00044-012-0300-y
https://doi.org/10.1007/s00044-012-0300-y
3. Deniz, Nahide Gülşah; Ibis, Cemil; Gokmen, Zeliha; Stasevych, Maryna; Novikov, Volodymyr; … Ozyurek, Mustafa; Guclu, Kubilay; Karakas, Didem; Ulukaya, Engin (2015). Design, Synthesis, Biological Evaluation, and Antioxidant and Cytotoxic Activity of Heteroatom-Substituted 1,4-Naphtho- and Benzoquinones. Chemical and Pharmaceutical Bulletin, 63(12), 1029-1039. doi:10.1248/cpb.c15-00607
https://doi.org/10.1248/cpb.c15-00607
4. Sieveking, Ivan; Thomas, Pablo; Estévez, Juan C.; Quiñones, Natalia; Cuéllar, Mauricio A.; Villena, Juan; Espinosa-Bustos, Christian; Fierro, Angélica; Tapia, Ricardo A.; Maya, Juan D.; López-Muñoz, Rodrigo; Cassels, Bruce K.; Estévez, Ramon J.; Salas, Cristian O. (2014). 2-Phenylaminonaphthoquinones and related compounds: Synthesis, trypanocidal and cytotoxic activities. Bioorganic & Medicinal Chemistry, 22(17), 4609-4620. doi:10.1016/j.bmc.2014.07.030
https://doi.org/10.1016/j.bmc.2014.07.030
5. Prachayasittikul, V., Pingaew, R., Worachartcheewan, A., Ruchirawat, S., & Prachayasittikul, V. (2014). Synthesis, anticancer activity and QSAR study of 1,4-naphthoquinone derivatives. European Journal of Medicinal Chemistry, 84, 247-263. doi:10.1016/j.ejmech.2014.07.024
https://doi.org/10.1016/j.ejmech.2014.07.024
6. Ibis, C., Shntaif, H., Bahar, H., & Ayla, S. (2015). An investigation of nucleophilic substitution reactions of 2,3-dichloro-1,4-naphthoquinone with various nucleophilic reagents. Journal of the Serbian Chemical Society, 80(6), 731-738. doi:10.2298/jsc141124021i
https://doi.org/10.2298/JSC141124021I
7. Shakh, Y. U., Romanenko, I., Slesarchuk, M., Syngaevsky, V., Kovalchuk, O., Bolibrukh, K., Karkhut, A., … O., Polovkovych, S. & Novikov, V. (2017). Synthesis and Antimicrobial Activity of 1,4-Naphthoquinones Derivatives with [1,2,4]-Triazole-3-thione Substitution. Indian Journal of Pharmaceutical Sciences, 79(4), 650-654. doi:10.4172/pharmaceutical-sciences.1000275
https://doi.org/10.4172/pharmaceutical-sciences.1000275
8. Tandon, V. K., Singh, R. V., & Yadav, D. B. (2004). Synthesis and evaluation of novel 1,4-naphthoquinone derivatives as antiviral, antifungal and anticancer agents. Bioorganic & Medicinal Chemistry Letters, 14(11), 2901-2904. doi:10.1016/j.bmcl.2004.03.047
https://doi.org/10.1016/j.bmcl.2004.03.047
9. Phillips, R. M., Jaffar, M., Maitland, D. J., Loadman, P. M., …, Patterson, A.V. & Stratford, I. J. (2004). Pharmacological and biological evaluation of a series of substituted 1,4-naphthoquinone bioreductive drugs. Biochemical Pharmacology, 68(11), 2107-2116. doi:10.1016/j.bcp.2004.08.007
https://doi.org/10.1016/j.bcp.2004.08.007
10. Mathew, N., Karunan, T., Srinivasan, L., & Muthuswamy, K. (2010). Synthesis and screening of substituted 1,4-naphthoquinones (NPQs) as antifilarial agents. Drug Development Research, 71, 188-196. doi:10.1002/ddr.20357
https://doi.org/10.1002/ddr.20357
11. Kurban, S., Deniz, N. G., Sayil, C., Ozyurek, M., Guclu, K., Stasevych, M., Zvarych, V., Komarovska-Porokhnyavets, O. & Novikov, V. (2019). Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-Substituted. Heteroatom Chemistry, 2019, 1-12. doi:10.1155/2019/1658417
https://doi.org/10.1155/2019/1658417
12. Yildirim, H. (2017). Synthesis and Structural Analysis of Some New Sulfanyl Amino 1,4-Naphthoquinone Derivatives. Journal of the Turkish Chemical Society, Section A: Chemistry, 5(1), 149-158. doi: 10.18596/ jotcsa.335894
https://doi.org/10.18596/jotcsa.335894
13. Kotakemori, M., & Okada, K. (1966). Thin-layer Chromatography of Some Substituted Naphthoquinones. Agricultural and Biological Chemistry, 30(9), 935-936. doi: 10.1271/bbb1961.30.935
https://doi.org/10.1271/bbb1961.30.935
14. Smirnova O. Ya., Polyuzhyn I. P., Yatchyshyn Yo. Yo. (2018). Normalnofazova tonkosharova khromatografiya dlya cyklichnyh pokhidnyh 3-hloro-1,4-naftohinonu. Visnyk Nacionalnogo universytetu "Lvivska politehnika". Himiya, texnologiya rechovyn ta yih zastosuvannya, 886, 14-22.
15. Smirnova O. Ya., Poliuzhyn I. P., Yatchyshyn Yo. Yo. (2018). Zalezhnosti mizh strukturoiu aminokyslotnykh pokhidnykh 3-khlor-1,4-naftokhinonu ta yikh utrymuvanniam v umovakh priamofazovoi tonkosharovoi khromatohrafii. Pytannia khimii ta khimichnoi tekhnolohii, 4 (119), S. 59-68. Retrieved from: http://udhtu.edu.ua/public/userfiles/file/VHHT/2018/4/Smirnova.pdf
16. Poliuzhyn Ihor, Smirnova Oksana, Yatchyshyn Yosyp (2018). Thin Layer Chromatography for Some Derivatives of 1,4-Naphthoquinone. - 8-th International Joint Youth Science Forum "Litteris et Artibus" (November, 22-24, 2018) / Proceedings. Lviv: "Lviv Polytechnic Press" (1 CD-ROM). P. 162-167.
https://doi.org/10.23939/lea2018.01.162
17. Snyder L. R. (1968). Principles of adsorption chromatography. New York: Dekker
18. Snyder L. R., Kirkland J. J., Dolan J. W. (2010). Introduction to Modern Liquid Chromatography. John Wiley & Sons, Inc.
https://doi.org/10.1002/9780470508183
19. Shandrenko, S. H., Holovin, A. S., Dmytrenko, M. P., Yurchenko, A. I., Babycheva, O. F. (2002). Kompiuterna reiestratsiia ta analiz rezultativ tonkosharovoi khromatohrafii. Zhurnal Khromatohrafichnoho tovarystva, 2(4), 22-30. doi: 10.15407/zht.2002.2.4.22
20. Snyder, L. R. (1974). Classification of the solvent properties of common liquids. Journal of Chromatography A, 92(2), 223-230. doi:10.1016/s0021-9673(00)85732-5
https://doi.org/10.1016/S0021-9673(00)85732-5
21. Snyder, L. R., Carr, P. W., & Rutan, S. C. (1993). Solvatochromically based solvent-selectivity triangle. Journal of Chromatography A, 656 (1-2), 537-547. doi:10.1016/0021-9673(93)80818-s
https://doi.org/10.1016/0021-9673(93)80818-S