Investigation of the interaction of ethyl acetoacetate with nano alumina particle as Lewis acid in acetonitrile solvent

doi:10.1007/s11458-011-0247-4

Front Chem Chin

2011, Vol. 6

Issue (3) : 248-252 https://doi.org/10.1007/s11458-011-0247-4

RESEARCH ARTICLE

Investigation of the interaction of ethyl acetoacetate with nano alumina particle as Lewis acid in acetonitrile solvent

Asadollah FARHADI¹(

), Mohammad Ali TAKASSI¹, Mandana DAYER²

1. Faculty of Science, Petroleum University of Technology, Ahwaz 61981-44471, Iran; 2. Department of Chemistry, Science and Research Branch, Islamic Azad University, Khouzestan, Iran

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Abstract

The enol form of ethyl acetoacetate (EAA) displays interesting spectroscopic characteristics; this form of ethyl acetylacetate is very important in condensation reaction. In this investigation, we have studied the interactions and the complex formation constants (K_f) with nano alumina (10–20 nm) particle and alumina (mesh 135) compounds as Lewis acids in the acetonitrile solvent using absorption spectroscopy and related calculations. Furthermore, in this study we calculated the thermodynamic parameters of this reaction. The trend of reactivity of the ethyl acetoacetate (EAA) complexes toward the above Lewis acids, based on the solvent as follows: nano alumina compound>alumina compound.

Keywords complex formation constant ethyl acetoacetate nano alumina alumina thermodynamic

Corresponding Author(s): FARHADI Asadollah,Email:farhadichem@yahoo.com

Issue Date: 05 September 2011

Cite this article:

Asadollah FARHADI,Mohammad Ali TAKASSI,Mandana DAYER. Investigation of the interaction of ethyl acetoacetate with nano alumina particle as Lewis acid in acetonitrile solvent[J]. Front Chem Chin, 2011, 6(3): 248-252.

URL:

https://academic.hep.com.cn/fcc/EN/10.1007/s11458-011-0247-4
https://academic.hep.com.cn/fcc/EN/Y2011/V6/I3/248

Fig.1 Keto-enol tautomerization of EAA with different Lewis acids in the acetonitrile solvent at various temperatures

Fig.2 The absorption spectra of EAA with AlO (nano) in acetonitrile as solvent at different temperatures

Tab.1 Data of wavelengths ( nm) and absorption bond () of ethyl acetoacetate in acetonitrile solvent at room temperature

Tab.2 The fixed wavelengths (242 nm) and absorption bond () of EAA in various systems at room temperature

Fig.3 A) Plots of () / vs. () for EAA complex with AlO (nano) at various temperatures ( = 25°C-45°C) in acetonitrile; B) Plots of () / vs. () for EAA complex with AlO at various temperatures ( = 25°C-45°C) in acetonitrile.

Fig.4 (a) Plot of ln vs. 1/for EAA complex with AlO (nano) in acetonitrile; (b)-(d) Plot of ln vs. 1/ for EAA complex with AlO in acetonitrile

Tab.3 The formation constants (mol/L) for EAA complex with AlO (nano) (10-20 nm) in acetonitrile solvent

Tab.4 The formation constants (mol/L) for EAA complex with AlO (mesh 135) in acetonitrile solvent

Tab.5 The thermodynamic parameter values (?H°, ?S° and ?G°) for EAA with AlO (nano) in acetonitrile solvent at room temperature

Tab.6 The thermodynamic parameter values (?H°, ?S° and ?G°) for EAA with AlO in acetonitrile solvent at room temperature

Tab.7 Data of wavelengths ( /nm) and absorption bonds () of ethyl acetoacetate (EAA) in acetonitrile solvent with two Lewis acids at various temperatures

1	Siedle, A. R., Comprehensive Coordination Chemistry, vol. 2, ed., G. Wilkinson, Pergamon Press, Oxford, 1987, pp. 365-412
2	Mehrotra, R. C.; Bohra, R.; Gaur, D. P., Metal β-Diketonates and Allied Derivatives, Academic Press, London, 1978
3	Fackler, J. P. Jr, Prog. Inorg. Chem . 1966, 7, 361-425 doi: 10.1002/9780470166086.ch6
4	Kawaguchi, S., Coord. Chem. Rev . 1986, 70, 51-84 . doi: 10.1016/0010-8545(86)80035-2
5	Garnovskii, A. D., Koord. Khim. 1992, 18, 675-680
6	Hinckley, C. C., J. Am. Chem. Soc. 1969, 91, 5160-5162 doi: 10.1021/ja01046a038 pmid:5798101
7	Wenzel, T. J.; Bettes, T. C.; Sadlowski, J. E.; Sievers, R. E., J. Am. Chem. Soc . 1980, 102, 5903-5904 doi: 10.1021/ja00538a032
8	Wenzel, T. J.; Zaia, J., J. Org. Chem . 1985, 50, 1322-1324 doi: 10.1021/jo00208a041
9	Brecher, C.; Lempicki, A.; Samelson, H., J. Chem. Phys . 1965, 42, 1081-1096 doi: 10.1063/1.1696045
10	Nugent, L. J.; Bhaumik, M. L.; George, S.; Lee, S. M., J. Chem. Phys . 1964, 41, 1305 doi: 10.1063/1.1726064
11	Poskanzer, A. M.; Foreman, B. M., J. Inorg. Nucl. Chem . 1961, 16, 323-336 doi: 10.1016/0022-1902(61)80507-1
12	Testa, C., Anal. Chim. Acta 1961, 25, 525
13	Ikehata, A.; Shimizu, T., Bull. Chem. Soc. Jpn. 1965, 38, 1385-1388 doi: 10.1246/bcsj.38.1385
14	Anjaneyulu, Y.; Rao, R. P.,Synth. React. Inorg. Metal-Org. Chem. 1986, 16, 257-261
15	Keppler, B. K.; Friesen, C.; Moritz, H. G.; Vongerichten, H.; Vogel, E., Struct. Bonding (Berlin) 1991, 78, 97-127
16	Marciniak, B.; Buono-Core, G. E., J. Photochem. Photobiol. Chem . 1990, 52, 1-25 doi: 10.1016/1010-6030(90)87085-P
17	Hubert-Pfalzgraf, L. G., Appl. Organomet. Chem . 1992, 6, 627-643 doi: 10.1002/aoc.590060805
18	Sievers, R. E.; Turnipseed, S. B.; Huang, L.; Lagalante, A. F., Coord. Chem. Rev . 1993, 128, 285-291 doi: 10.1016/0010-8545(93)80035-4
19	Robards, K.; Patsalides, E.; Dilli, S., J. Chromatogr. A 1987, 411, 1-41 doi: 10.1016/S0021-9673(00)93958-X
20	Komarov, V. A., Zh. Anal. Khim . 1976, 31, 366-375
21	van Leeuwen, P. W. N. M., Recl. Trav. Chim. Pays Bas 1968, 87, 396-402 doi: 10.1002/recl.19680870409
22	van Leeuwen, P. W. N. M.; Praat, A. P., Inorg. Chim. Acta 1970, 4, 101-104 doi: 10.1016/S0020-1693(00)93248-1
23	Allred, A. L.; Thompson, D. W., Inorg. Chem . 1968, 7, 1196-1201 doi: 10.1021/ic50064a029
24	Blanco, C. A.; Hynes, M. J., Can. J. Chem . 1992, 70, 2285-2289 doi: 10.1139/v92-287
25	Pearson, R. G.; Anderson, O. P., Inorg. Chem . 1970, 9, 39-46 doi: 10.1021/ic50083a008
26	Fay, D. P.; Nichols, A. R.; Sutin, N., Inorg. Chem . 1971, 10, 2096-2101 doi: 10.1021/ic50104a002
27	Ketelaar, J. A. A.; van de Stolpe, C.; Coulsmith, A.; Dzcubes, W., Rec. Trav. Chim . 1952, 71, 1104-1114 doi: 10.1002/recl.19520711108
28	Asadi, M.; Kianfar, A. H.; Hemateenejad, B., J. Chem. Res . 2002, 520-523 doi: 10.3184/030823402103170600
29	Khodaei, M. M.; Khosropour, A. R.; Beygzadeh, M., Synth. Commun . 2004, 34, 1551-1557 doi: 10.1081/SCC-120030742

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