Article Sidebar

Submitted
October 17, 2016
Accepted
October 17, 2016
Published
October 17, 2016
Download
PDF
Statistic
Read Counter : 1504 Download : 4728

Main Article Content

Abstract

Telah dilakukan sintesis turunan senyawa kalkon tersubstitusi gugus nitro dan hidroksi melalui reaksi kondensasi Claisen Schmidt. Tujuan penelitian ini adalah untuk mensintesis senyawa kalkon yang tersubstitusi gugus hirdoksi dan nitro dalam medium basa, dan mempelajari pengaruh gugus tersebut dalam reaksi kondendasi. Kalkon 1 disintesis dari 4-nitroasetofenon dan vanilin menggunakan katalis NaOH 60% (b/v dalam akuades) melalui pengadukan selama 24 jam. Kalkon 2 didapatkan dari reaksi antara 4-nitroasetofenon dan veratraldehida dengan katalis NaOH 15% selama 4 jam, sedangkan kalkon 3 disintesis dari 4-nitroasetofenon dan 6-nitroveratraldehida dalam 5% NaOH 10 tetes. Produk hasil sintesis dikarakterisasi dengan FTIR, GC-MS dan 1H-NMR.

Hasil penelitian menunjukkan bahwa senyawa kalkon telah berhasil disintesis dengan rendemen berturut-turut sebesar 16,80; 75,83; dan 44,11 % dalam medium basa. Dari penelitian ini, dapat disimpulkan bahwa adanya gugus hidroksi dari sumber aldehida aromatik pada kalkon 1 menghambat terjadinya reaksi, sedangkan gugus nitro yang terikat pada aldehida aromatik menjadi kendala pada reaksi kalkon 3 karena sifatnya yang sensitif terhadap cahaya.

Keywords

kalkon kondensasi Claisen Schmidt 4-nitroasetofenon 6-nitroveratraldehida

Article Details

License

Authors who publish with this journal agree to the following terms:

  1. Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgment of the work's authorship and initial publication in this journal.
  2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgment of its initial publication in this journal.
  3. Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).
How to Cite
Fauzi’ah, L., & Wahyuningsih, T. D. (2016). Synthesis of Chalcones Substituted with Nitro and Hydroxyl Group in Alkaline Medium. EKSAKTA: Journal of Sciences and Data Analysis, 16(2), 103–114. https://doi.org/10.20885/eksakta.vol16.iss2.art5
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
Crossref
Scopus
Google Scholar
Europe PMC

References

  1. Arty, I.S., Rohmawati, D., 2014, Optimization of Condensation Reaction Time Between Vanillin and p-Nitroacetophenone in Acid Catalysts, J.Sains Dasar 3(1): 34-38.
  2. Choudhary, A.N. dan Juyal, V., 2011, Synthesis of Chalcone and Their Derivatives as Antimicrobial Agents, Int. J. Pharm. Pharm. Sci., 3-6.
  3. Dias, T.A., Duarte, L.C., Lima, C.F. and Proenca, M.F., 2013, Superior Anticancer Activity of Halogenated Chalcones and Flavonols Over the Natural Flavonols Quercetin, Eur. J. Med. Chem., 65, 500-10.
  4. Hammuda, A., Shalaby, R., Rovida, S., Edmondson, D.E., Binda, C., Khalil, A., 2016, Design and Synthesis of Novel Chalcones as Potent Selective Monoamine Oxidase-B Inhibitors, Eur. J. Med. Chem., doi:10.1016/j.ejmech.2016.02.038.
  5. Hans, R.H., Guantai, E.M., Lategan, C., Smith, P.J., Wan, B., Franzblau, S.G., Gut, J., Rosethal, P.J., Chibale, K., 2009, Synthesis, Antimalarial and Antitubercular Activity of Acetylenic Chalcones, Bioorg. Med. Chem. Lett. 20: 942-944.
  6. Jagadeesh, M., Lavanya, M., Babu, B.H., Hong, K., Ma, R., Kim, J., and Kim. T.K., 2015, Synthesis and Detailed Spectroscopic Characterization of Various Hydroxy-functionalized Fluorescent Chalcones: A Combined Experimental and Theoretical Study, Spectrochim Acta A Mol Biomol Spectrosc., 150: 557-564, http://dx.doi.org/10.1016/j.saa.2015.05.085.
  7. Janaki, P., Sekar, K.G., Thirunarayanan, G., 2012, Synthesis, Spectral Correlation and Insect Antifeedant Activities of Some 2-Benzimidazole Chalcones, J. Saudi Chem. Soc. 20; 58-68, http://dx.doi.org/10.1016/j.jscs.2012.11.013.
  8. Lawrence, N.J., Patterson, R.P., Ooi, L.L., Cook, D., and Ducki, S., 2006, Effect of Alfa-Substitutions on Structure and Biological Activity of Anticancer Chalcones, Med. Chem. Lett. (16): 5844-48.
  9. Mahapatra, D.K. dan Bharti, S.K., 2016, Therapeutic Potential of Chalcones as Cardiovascular Agents, Life Sci.148: 154–172, http://dx.doi.org/10.1016/j.lfs.2016.02.048.
  10. Nowakowska, Z., 2007, A Review of Anti-infective and Anti-inflammatory Chalcones, Eur. J. Med. Chem. 42: 125-137, doi:10.1016/j.ejmech.2006.09.019.
  11. Singh, P., Anand, A., and Kumar, V., 2014, Recent Developments in Biological Activities of Chalcones: A Mini Review, Eur. J. Med. Chem. 85: 758-777, http://dx.doi.org/10.1016/j.ejmech.2014.08.033.
  12. Susanti, E. dan Redjeki, T., 2011, Synthesis of 2',4'-Dihydroxy-3,4-Dimethoxychalcone from Vanillin by Claisen-Schmidt Condensation, Prosiding Seminar Kimia dan Pendidikan Kimia UNS, 7 Mei 2011, Solo.
  13. Wan, M., Xu, L., Hua L., Li, A., Li, S., Lu, W., Pang, Y., Cao, C., Liu, X., and Jiao, P., 2014, Synthesis and Evaluation of Novel Isoxazolyl Chalcones as Potential Anticancer Agents, Bioorg. Chem.(54): 38–43, http://dx.doi.org/10.1016/j.bioorg.2014.03.004.
  14. Vanangamudi, G., Subramanian, M., Jayanthi, P., Arulkumaran, R., Kamalakkannan, D. and Thirunarayanan, G., 2011, IR and NMR Spectral Studies of Some 2-Hydroxy-1-Naphthyl Chalcones: Assessment of Substituent Effects, Arabian J. Chem., 1-8.