Journals / Afyon Kocatepe Üniversitesi Fen ve Mühendislik Bilimleri Dergisi / 2026 / Cilt: 24 Sayı: 4

Synthesis and Characterization of Novel Selenium N,S-heterocyclic carbene compounds

Yeni Selenyum N,S-heterosiklik Karben Bileşiklerinin Sentezi ve Karakterizasyonu

Deniz Demir Atlı(MANISA CELAL BAYAR UNIVERSITY)0000-0001-8442-4916
Pages
947–954
Publication Date
2024-08-20
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Also, molecular weights of the selenium adducts were validated by LC-MS/MS analysis.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Two novel benzothiazolium salts, N-(4-methoxybenzyl)benzothiazolium chloride (1a) and N-(4-tert-butylbenzyl)benzothiazolium bromide (1b), were prepared by using benzothiazole and related benzyl halides.
📊
Key Findings & Data:Selenourea N,S-heterocyclic-based derivatives (2a and 2b) were obtained by the reaction of the salts with selenium in the presence of KOBut base. 1H NMR, 13C NMR and elemental analysis were used for characterization of the synthesized compounds.
💡
Conclusion & Impact:Also, molecular weights of the selenium adducts were validated by LC-MS/MS analysis.
🔬Design:Araştırma Makalesi
📍Scope:Comprehensive Sample
⚙️Variables:Benzotiyazolyum · S-heterosiklik karben · Selenyum

Abstract

Two novel benzothiazolium salts, N-(4-methoxybenzyl)benzothiazolium chloride (1a) and N-(4-tert-butylbenzyl)benzothiazolium bromide (1b), were prepared by using benzothiazole and related benzyl halides. Selenourea N,S-heterocyclic-based derivatives (2a and 2b) were obtained by the reaction of the salts with selenium in the presence of KOBut base. 1H NMR, 13C NMR and elemental analysis were used for characterization of the synthesized compounds. Also, molecular weights of the selenium adducts were validated by LC-MS/MS analysis.

Özet

Benzotiyazol ve ilgili benzil halojenürler kullanılarak iki yeni benzotiyazolyum tuzu N-(4-metoksibenzil)benzotiyazolyum klorür (1a) ve N-(4-tert-bütilbenzil)benzotiyazolyum bromür (1b) hazırlandı. Selenoüre N,S-heterosiklik bazlı türevler (2a ve 2b), tuzların KOBut bazı varlığında selenyum ile reaksiyonu sonucu elde edildi. Sentezlenen bileşiklerin karakterizasyonu için 1H NMR, 13C NMR ve elementel analiz kullanıldı.. Ayrıca, selenyum katılma ürünlerinin molekül ağırlıkları LC-MS/MS analizi ile doğrulandı.

🔖

Cite This Article

Atlı, D. D. (2024). Synthesis and Characterization of Novel Selenium N,S-heterocyclic carbene compounds. Afyon Kocatepe Üniversitesi Fen ve Mühendislik Bilimleri Dergisi, Cilt: 24 Sayı: 4, 947–954. https://doi.org/10.35414/akufemubid.1429062

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (34)

  1. Arduengo III, A.J., Goerlich, J.R., Marshall, W.J., 1997. A stable thiazol-2-ylidene and its dimer. Liebigs Annalen/ Recueil, 1997, 365–374. https:/doi.org/10.1002/jlac.199719970213
  2. Banerjee, B., Koketsu, M., 2017. Recent developments in the synthesis of biologically relevant selenium-containing scaffolds. Coordination Chemistry Reviews, 339, 104–127. https:/doi.org/10.1016/j.ccr.2017.03.008
  3. Breslow, R., 1958. On the mechanism of thiamine action. IV. 1. Evidence from studies on model systems. Journal of American Chemical Society, 80, 3719-3726. https://doi.org/10.1021/ja01547a064
  4. Calo, V., Del Sole, R., Nacci, A., Schingaro, E., Scordari, F., 2000. Synthesis and crystal structure of bis(2,3-dihydro-3-methylbenzothiazole-2-ylidene)-palladium (II) diiodide: The first palladium complex with benzothiazole carbene ligands suitable for homogeneous catalysis. European Journal of Organic Chemistry, 2000, 869–871. https:/doi.org/10.1002/(SICI)1099-0690(200003)2000:6%3C869::AID-EJOC869%3E3.0.CO;2-I
  5. Cardin, D.J., Çetinkaya, B., Çetinkaya, E., Lappert, M.F., 1973. Carbene complexes. Part I.Electron-rich olefins as a source of carbene complexes of platinum(II) and palladium(II); and some experiments with (CF3)2CN2. Journal Of Chemical Society, Dalton Transactions, 514–522. https://doi.org/10.1039/DT9730000514 Časar, Z., Lorcy, D., Leban, I., Maréchal, A.M. 2002. A novel approach to N,N’-dimethyl and N,N’-ethylene bridged dibenzodithiadiazafulvalene. Acta Chimica Solvenica, 49, 871-883.
  6. Cierpiał, T., Łuczak, J., Kwiatkowska, M., Kiełbasiński, P., Mielczarek, L., Wiktorska, K., Chilmonczyk, Z., Milczarek, M., Karwowska, K., 2016. Organofluorine isoselenocyanate analogues of sulforaphane: synthesis and anticancer activity. ChemMedChem, 11, 2398–2409. https:/doi.org/10.1002/cmdc.201600442
  7. Demir Atlı, D., 2020. Synthesis and Characterization of Benzothiazolium Salts containing substituted benzyl groups. Science and Mathematics Sciences. Mehtap Düz (ed.), IVPE, 1-11.
  8. Demir Atlı, D., 2021. Synthesis, characterization and catalytic properties of cationic N-heterocyclic carbene silver complexes. Turkish Journal of Chemistry, 45, 577-584. https:/doi.org/10.3906/kim-2010-26
  9. Devillanova, F.A., Verani, G., 1980. ‘Selenation’ as a diagnostic aid to reinvestigate the infrared spectra of benzimidazole-, benzoxazole- and benzothiazole-2-thiones. Australian Journal of Chemistry, 33, 279-286. https://doi.org/10.1071/CH9800279
  10. Dince, C.C., Meoded, R.A., Hilvert, D., 2017. Synthesis and characterization of catalytically active thiazolium gold(I)-carbenes. Chemical Communications, 53, 7585–7587. https:/doi.org/10.1039/C7CC03791K
  11. Ding, N., Zhang, J., Hor, A., 2009. Formation and crystallographic elucidation of stable [4+2]-coordinate nickel(II) N,S-heterocyclic carbene (NSHC) complexes. Dalton Transactions, 10, 1853–1858. https:/doi.org/10.1039/B815876B
  12. Ding, N., Hor, T.S.A., 2010. Ruthenium(II) N,S-heterocyclic carbene complexes and transfer hydrogenation of ketones. Dalton Transactions, 39, 10179–10185. https:/doi.org/10.1039/C0DT00562B
  13. Fraser, P.J., Roper, W.R., Stone F.G.A., 1974. Carbene complexes of iridium, rhodium, manganese, chromium, and iron containing thiazolidinylidene and pyridinyl- idene ligands. Journal Of Chemical Society, Dalton Transactions, 7, 760-764. https://doi.org/10.1039/DT9740000760
  14. Gutiérrez, A., Gimeno, M.C., Marzo, I., Metzler-Nolte, N., 2014. Synthesis, characterization, and cytotoxic activity of AuIN,S-heterocyclic carbenes derived from peptides containing L-thiazolylalanine. European Journal of Inorganic Chemistry, 2014, 2512–2519. http:/dx.doi.org/10.1002/ejic.201402103
  15. Han, X., Koh, L.L., Weng, Z., Hor, T.S.A., 2009. One-step formation of cyclometallated Au(III) N,S-heterocyclic carbene: crystallographic analysis. Dalton Transactions, 7248-7252. https://doi.org/10.1039/B909661B
  16. Huang, M., Li, Y., Lan, X.B., Liu, J., Zhao, C., Liu, Y., Ke, Z., 2021. Ruthenium(II) complexes with N-heterocyclic carbene–phosphine ligands for the N-alkylation of amines with alcohols. Organic & Biomolecular Chemistry, 19, 3451-3461. https:/doi.org/10.1039/D1OB00362C
  17. Huynh, H.V., Meier, N., Pape, T., Hahn, F.E., 2006. Benzothiazolin-2-ylidene complexes of iridium(I). Organometallics, 25, 3012-3018. https://doi.org/10.1021/om060006i
  18. Kamal, A., Nazari V., M., Yaseen, M., Iqbal, M.A., Ahamed, M.B.K., Majid, A.S.A., Bhatti, H.N., 2019. Green synthesis of selenium-N-heterocyclic carbene compounds: Evaluation of antimicrobial and anticancer potential. Bioorganic Chemistry, 90, 103042. https:/doi.org/10.1016/j.bioorg.2019.103042
  19. Karakaş, H., Güzel, M., Ak, M., Kılınçarslan, R., Özdemir, N., 2022. N,S-heterocyclic carbene containing benzothiazol-2-ylidene-Ru(II) and Pd(II) new complexes functionalized with butyl linked carbazole moiety: Synthesis, characterization and their catalytic efficiency and electropolymerizations. European Polymer Journal, 181, 111630. https:/doi.org/10.1016/j.eurpolymj.2022.111630
  20. Liang, Y., Zhou, Y., Deng, S., Chen, T., 2016. Microwave-assisted syntheses of benzimidazole-containing selenadiazole derivatives that induce cell-cycle arrest and apoptosis in human breast cancer cells by activation of the ROS/AKT pathway. ChemMedChem, 11, 2339–2346. https:/doi.org/10.1002/cmdc.201600261
  21. Oruc, Z.I., Gok, L., Turkmen, H., Sahin, O., Buyukgungor, O., Cetinkaya, B., 2016. Pianostool benzothiazol-2-ylidene Ru(II) complexes for effective transfer hydrogenation of carbonyls. Journal of Organometallic Chemistry, 807, 36–44. https:/doi.org/10.1016/j.jorganchem.2016.02.003
  22. Papp, L.V., Lu, J., Holmgren, A., Khanna, K.K., 2007. From selenium to selenoproteins: synthesis, identity, and their role in human health. Antioxidant Redox Signaling, 9, 775–806. https:/doi.org/10.1089/ars.2007.1528
  23. Purohit, V.B., Karad, S.C., Patel, K.H., Raval, D.K., 2014. Cu(N-heterocyclic carbene) chloride: an efficient catalyst for multicomponent click reaction for the synthesis of 1,2,3-triazoles in water at room temperature. RSC Advances, 4, 46002–46007. https:/doi.org/10.1039/C4RA08412H
  24. Purohit, V.B., Karad, S.C., Patel, K.H., Raval, D.K., 2016. Palladium N-heterocyclic carbene catalyzed regioselective thiolation of 1-aryl-3-methyl-1H-pyrazol-5(4H)-ones using aryl thiols. Tetrahedron, 72, 1114-1119. https://doi.org/10.1016/j.tet.2016.01.012
  25. Rafique, J., Saba, S., Canto, R.F.S., Frizon, T.E.A., Hassan, W., Waczuk, E.P., Jan, M., Back, D.F., Da Rocha, J.B.T., Braga, A.L., 2015. Synthesis and biological evaluation of 2-picolylamide-based diselenides with non-bonded interactions. Molecules, 20, 10095–10109. https:/doi.org/10.3390/molecules200610095
  26. Spengler, G., Gajdács, M., Mar´c, M.A., Domínguez-Álvarez, E., Sanmartín, C., 2019. Organoselenium compounds as novel adjuvants of chemotherapy drugs—a promising approach to fight cancer drug resistance. Molecules, 24, 336. https:/doi.org/10.3390%2Fmolecules24020336
  27. Sun, J., Zheng, X., Li, H., Fan, D., Song, Z., Ma, H., Hua, X., Hui, J., 2017. Monodisperse selenium-substituted hydroxyapatite: controllable synthesis and biocompatibility. Materials Science and Engineering: C, 73, 596–602. https:/doi.org/10.1016/j.msec.2016.12.106
  28. Yaqoob, M., Gul, S., Zubair, N.S., Iqbal, J., Iqbal, M.A., 2020. Theoretical calculation of selenium N-heterocyclic carbene compounds through DFT studies: Synthesis, characterization and biological potential. Journal of Molecular Structure, 1204, 127462. https:/doi.org/10.1016/j.molstruc.2019.127462
  29. Yen, S.K., Koh, L.L., Hahn, F.E., Huynh, H.V., Hor, T.S.A., 2006. Convenient entry to mono and dinuclear palladium(II) benzothiazolin-2-ylidene complexes and their activities toward heck coupling. Organometallics, 25, 5105–5112. https:/doi.org/10.1021/om060510n
  30. Yen, S.K., Koh, L.L., Huynh, H.V., Hor, T.S.A., 2007. Pd(II) complexes of N,S-heterocyclic carbenes with pendant and coordinated allyl function and their Suzuki coupling activities. Dalton Transactions, 35, 3952–3958. https:/doi.org/10.1039/B706968E
  31. Yen, S.K., Koh, L.L., Huynh, H.V., Hor, T.S.A., 2008. Pd(II) complexes with mixed benzothiazolin-2-ylidene and phosphine ligands and their catalytic activities toward C-C coupling reactions. Dalton Transactions, 5, 699–706. https:/doi.org/10.1039/B713152F
  32. Yen, S.K., Young, D.J., Huynh, H.V., Koh, L.L., Hor, T.S.A., 2009. Unexpected coordination difference in geometric-isomerism between N,S- and N,N-heterocyclic carbenes in cyclometallated platinum(II). Chemical Communications, 6831-6833. https://doi.org/10.1039/B914036K
  33. Zhao, S., Yang, Z., Jiang, G., Huang, S., Bian, M., Lu, Y., Liu, W., 2021. An overview of anticancer platinum N-heterocyclic carbene complexes. Coordination Chemistry Reviews, 449, 214217. https:/doi.org/10.1016/j.ccr.2021.214217
  34. Spengler, G., Gajdács, M., Mar´c, M.A., Domínguez-Álvarez, E., Sanmartín, C., 2019. Organoselenium compounds as novel adjuvants of chemotherapy drugs—a promising approach to fight cancer drug resistance. Molecules, 24, 336. https:/doi.org/10.3390%2Fmolecules24020336