Effect of reactants' concentration on the ratio and yield of E,Z isomers of isatin-3-(4-phenyl)semicarbazone and N-methylisatin-3-(4-phenyl)semicarbazone

Chemical Papers

Volumn 67, Issue 1, 2013, Pages 117-126

  Jakusová, Klaudia ^a   Gáplovský, Martin ^a   Donovalová, Jana ^a   Cigáň, Marek ^a   Stankovičová, Henrieta ^a   Sokolík, Robert ^a   Gašpar, Jan ^a   Gáplovský, Anton ^a  

^a Faculty of Natural Sciences   (Slovakia)

Author keywords

concentration and solvent dependence; intermolecular interactions; isatinphenylsemicarbazones; synthesis of E,Z isomers

Indexed keywords

EID: 84866760348     PISSN: 03666352     EISSN: 13369075     Source Type: Journal    
DOI: 10.2478/s11696-012-0248-x     Document Type: Article

References (32)

1. Afrasiabi, Z., Sinn, E., Lin, W., Ma, Y., Campana, C., & Padhye, S. (2005). Nickel (II) complexes of naphthaquinone thiosemicarbazone and semicarbazone: Synthesis, structure, spectroscopy, and biological activity. Journal of Inorganic Biochemystry, 99, 1526-1531. DOI: 10.1016/j.jinorgbio.2005. 04.012.
2. Alarcón, S. H., Olivieri, A. C., Labadie, G. R., Cravero, R. M., & González-Sierra, M. (1995). Tautomerism of representative aromatic α-hydroxy carbaldehyde anils as studied by spectroscopic methods and AM1 calculations. Synthesis of 10-hydroxyphenanthrene-9-carbaldehyde. Tetrahedron, 51, 4619-4626. DOI: 10.1016/0040-4020(95)00002-p.
3. Borsche, W., & Meyer, R. (1921). Über Desoxy-indigo. Berichte der Deutschen Chemischen Gesellschaft (A and B Series), 54, 2854-2856. DOI: 10.1002/cber.19210541037.
4. Brancato, G., Coutrot, F., Leigh, D. A., Murphy, A., Wong, J. K. Y., & Zerbetto, F. (2002). From reactants to products via simple hydrogen-bonding networks: Information transmission in chemical reactions. PNAS, 99, 4967-4971. DOI: 10.1073/pnas.072695799.
5. Cerchiaro, G., & da Costa Ferreira, A. M. (2006). Oxindoles and copper complexes with oxindole-derivatives as potential pharmacological agents. Journal of the Brazilian Chemical Society, 17, 1473-1485. DOI: 10.1590/s0103-50532006000800003.
6. Chai, H., Liu, G., Liu, L., Jia, D., Guo, Z., & Lang, J. (2005). Crystal structure and spectroscopic study on photochromism of 1,3-diphenyl-4-(4′-fluoro)benzal-5-pyrazolone N(4)-phenyl semicarbazone. Journal of Molecular Structure, 752, 124-129. DOI: 10.1016/j.molstruc.2005.04. 047.
7. Cubero, E., Orozco, M., Hobza, P., & Luque, J. F. (1999). Hydrogen bond versus anti-hydrogen bond: A comparative analysis based on the electron density topology. Journal of Physical Chemistry A, 103, 6394-6401. DOI: 10.1021/jp990258f.
8. Dimmock, J. R., Vashishtha, S. C., & Stables, J. P. (2000). Urelylene anticonvulants and related compounds. Pharmazie, 55, 490-494.
9. Epshtein, L. M. (1979). Hydrogen bonds and the reactivity of organic compounds in proton transfer and nucleophilic substitution reactions. Russian Chemical Reviews, 48, 854-867. DOI: 10.1070/rc1979v048n09abeh002417.
10. Falkovskaia, E., Pivovarenko, V. G., & del Valle, J. C. (2002). Observation of a single proton transfer fluorescence in a biaxially symmetric dihydroxy diflavonol. Chemical Physics Letters, 352, 415-420. DOI: 10.1016/s0009-2614(01)01490-7.
11. Farghaly, M., Abbel-Wahab, B. F., & Ahmed, E. M. (2009). Synthesis, antiviral and antimicrobial screening of some new 2-oxoindoline derivatives. Chemistry of Heterocyclic Compounds, 45, 539-544. DOI: 10.1155/2008/362105.
12. Hadjoudis, E., Dziembowska, T., & Rozwadowski, Z. (1999). Photoactivation of the thermochromic solid di-anil of 2-hydroxy-5-methyl- isophthalaldehyde in β-cyclodextrin. Journal of Photochemistry and Photobiology A: Chemistry, 128, 97-99. DOI: 10.1016/s1010-6030(99)00126-4.
13. Jafri, L., Ansari, F. L., Jamil, M., Kalsoom, S., Qureishi, S., & Mirza, B. (2012). Microwave-assisted synthesis and bioevaluation of some semicarbazones. Chemical Biology and Drug Design, 79, 1-10. DOI: 10.1111/j.1747-0285.2012.01360.x.
14. Jia, C., Wu, B., Liang, J., Huang, X., & Yang, X. J. (2010). A colorimetric and ratiometric fluorescent chemosensor for fluoride based on proton transfer. Journal of Fluorescence, 20, 291-297. DOI: 10.1007/s10895-009- 0553-0.
15. Kang, I. J., Wang, L. W., Hsu, T. A., Yueh, A., Lee, C. C., Lee, Y. C., Chao, Y. S., Shih, S. R., Chern, J. H., & Lee, C. Y. (2011). Isatin-β-thiosemicarbazones as potent herpes simplex virus inhibitors. Bioorganic & Medicinal Chemistry Letters, 21, 1948-1952. DOI: 10.1016/j.bmcl.2011.02.037.
16. Kolehmainen, E., Ośmiałowski, B., Nissinen, M., Kauppinen, R., & Gawinecki, R. (2000). Substituent and temperature controlled tautomerism of 2-phenacylpyridine: the hydrogen bond as a configurational lock of (Z)-2-(2-hydroxy-2-phenylvinyl)pyridine. Journal of Chemical Society, Perkin Transactions 2, 2000, 2185-2191. DOI: 10.1039/b006879i.
17. Levy, D. H. (1980). Laser spectroscopy of cold gas-phase molecules. Annual Review of Physical Chemistry, 31, 197-225. DOI: 10.1146/annurev.pc.31. 100180.001213.
18. Li, Q. S., & Fang, W. H. (2003). Theoretical studies on structures and reactivity of 8-hydroxyquinoline and its one-water complex in the ground and excited states. Chemical Physics Letters, 367, 637-644. DOI: 10.1016/s0009-2614(02)01791-8.
19. Mehata, M. S., Joshi, H. C., & Tripathi, H. B. (2002). Excited-state intermolecular proton transfer reaction of 6-hydroxyquinoline in protic polar medium. Chemical Physics Letters, 359, 314-320. DOI: 10.1016/s0009-2614(02) 00716-9.
20. Otsubo, N., Okabe, C., Mori, H., Sakota, K., Amimoto, K., Kawato, T., & Sekiya, H. (2002). Excited-state intramolecular proton transfer in photochromic jet-cooled Nsalicylideneaniline. Journal of Photochemistry and Photobiology A: Chemistry, 154, 33-39. DOI: 10.1016/s1010-6030(02)00306-4.
21. Pal, M., Sharma, N. K., Priynka, P., & Jha, K. K. (2011). Synthetic and biological multiplicity of isatin: A review. Journal of Advanced Scientific Research, 2, 35-44.
22. Pandeya, S. N., Yogeeswari, P., & Stables, J. P. (2000). Synthesis and anticonvulant activity of 4-bromophenyl substituted aryl semicarbazones. European Journal of Medicinal Chemistry, 35, 879-886. DOI: 10.1016/s0223- 5234(00)01169-7.
23. Pandeya, S. N., Raja, A. S., & Stables, J. P. (2002). Synthesis of isatin semicarbazones as novel anticonvulsants role of hydrogen bonding. Journal of Pharmacy and Pharmaceutical Sciences, 5, 266-271.
24. Pandeya, S. N., Raja, A. S., & Nath, G. (2006). Synthesis and antimicrobial evaluation of some 4- or 6-chloroisatin derivatives. Indian Journal of Chemistry, 45B, 494-499.
25. Sathisha, M. P., Revankar, V. K., & Pai, K. S. R. (2008). Synthesis, structure, electrochemistry, and spectral characterization of bis-isatin thiocarbohydrazone metal complexes and their antitumor activity against ehrlich ascites carcinoma in swiss albino mice. Metal-Based Drugs, 1, 1-11. DOI: 10.1155/2008/362105.
26. Senthilkumar, L., Ghanty, T. K., & Ghosh, S. K. (2005). Electron density and energy decomposition analysis in hydrogenbonded complexes of azabenzenes with water, acetamide, and thioacetamide. Journal of Physical Chemistry A, 109, 7575-7582. DOI: 10.1021/jp052304j.
27. Sonawane, A. E., Pawar, Y. A., Nagle, P. S., Mahulikar, P. P., & More, D. H. (2009). Synthesis of 1,4-benzothiazine compounds containing isatin hydrazone moiety as antimicrobial agent. Chinese Journal of Chemistry, 27, 2049-2054. DOI: 10.1002/cjoc.200990344.
28. Sridhar, S. K., Saravanan, M., & Ramesh, A. (2001). Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives. European Journal of Medicinal Chemistry, 36, 615-625. DOI: 10.1016/s0223-5234(01)01255-7.
29. Verma, M., Pandeya, S. N., Singh, K. N., & Stables, J. P. (2004). Anticonvulsant activity of Schiff bases of isatin derivatives. Acta Pharmaceutica, 54, 49-56.
30. Verma, K., Pandeya, S. N., Singh, U. K., Gupta, S., Prashant, P., & Anurag Gautam, B. (2009). Synthesis and pharmacological activity of some substituted menthone semicarbazone and thiosemicarbazone derivatives. International Journal of Pharmaceutical Sciences and Nanotechnology, 1, 357-362.
31. Wu, D. L., Liu, L., Liu, G. F., & Jia, D. Z. (2007). Theoretical studies on geometrical properties and photochromic mechanism of two photochromic compounds. Journal of Molecular Structure: THEOCHEM, 806, 197-203. DOI: 10.1016/j.theochem.2006.11.027.
32. Zhao, Y., & Truhlar, D. G. (2008). The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta), 120, 215-241. DOI: 10.1007/s00214-007-0310-x.