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

Year 2024, , 947 - 954, 20.08.2024

Deniz Demir Atlı

https://doi.org/10.35414/akufemubid.1429062

Abstract

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.

Keywords

Benzotiyazolyum N,S-heterosiklik karben Selenyum Selenoüre

Project Number

BAP 2019/141

Thanks

This work was supported by the Scientific Research Project Fund of Manisa Celal Bayar University under project number 2019-141.

References

  • 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
  • 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
  • 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
  • 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
  • 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.
  • 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
  • Demir Atlı, D., 2020. Synthesis and Characterization of Benzothiazolium Salts containing substituted benzyl groups. Science and Mathematics Sciences. Mehtap Düz (ed.), IVPE, 1-11.
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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

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

Year 2024, , 947 - 954, 20.08.2024

Deniz Demir Atlı

https://doi.org/10.35414/akufemubid.1429062

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.

Keywords

Benzothiazolium N,S-heterocyclic carbene Selenium Selenourea

Project Number

BAP 2019/141

Thanks

This work was supported by the Scientific Research Project Fund of Manisa Celal Bayar University under project number 2019-141.

References

  • 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
  • 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
  • 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
  • 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
  • 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.
  • 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
  • Demir Atlı, D., 2020. Synthesis and Characterization of Benzothiazolium Salts containing substituted benzyl groups. Science and Mathematics Sciences. Mehtap Düz (ed.), IVPE, 1-11.
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
There are 33 citations in total.

Details

Primary Language English
Subjects Inorganic Chemistry (Other)
Journal Section Articles
Authors

Deniz Demir Atlı 0000-0001-8442-4916

Project Number BAP 2019/141
Early Pub Date July 23, 2024
Publication Date August 20, 2024
Submission Date January 31, 2024
Acceptance Date June 13, 2024
Published in Issue Year 2024

Cite

APA Demir Atlı, D. (2024). Synthesis and Characterization of Novel Selenium N,S-heterocyclic carbene compounds. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, 24(4), 947-954. https://doi.org/10.35414/akufemubid.1429062
AMA Demir Atlı D. Synthesis and Characterization of Novel Selenium N,S-heterocyclic carbene compounds. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. August 2024;24(4):947-954. doi:10.35414/akufemubid.1429062
Chicago Demir Atlı, Deniz. “Synthesis and Characterization of Novel Selenium N,S-Heterocyclic Carbene Compounds”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 24, no. 4 (August 2024): 947-54. https://doi.org/10.35414/akufemubid.1429062.
EndNote Demir Atlı D (August 1, 2024) Synthesis and Characterization of Novel Selenium N,S-heterocyclic carbene compounds. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 24 4 947–954.
IEEE D. Demir Atlı, “Synthesis and Characterization of Novel Selenium N,S-heterocyclic carbene compounds”, Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, vol. 24, no. 4, pp. 947–954, 2024, doi: 10.35414/akufemubid.1429062.
ISNAD Demir Atlı, Deniz. “Synthesis and Characterization of Novel Selenium N,S-Heterocyclic Carbene Compounds”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 24/4 (August 2024), 947-954. https://doi.org/10.35414/akufemubid.1429062.
JAMA Demir Atlı D. Synthesis and Characterization of Novel Selenium N,S-heterocyclic carbene compounds. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2024;24:947–954.
MLA Demir Atlı, Deniz. “Synthesis and Characterization of Novel Selenium N,S-Heterocyclic Carbene Compounds”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, vol. 24, no. 4, 2024, pp. 947-54, doi:10.35414/akufemubid.1429062.
Vancouver Demir Atlı D. Synthesis and Characterization of Novel Selenium N,S-heterocyclic carbene compounds. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2024;24(4):947-54.


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