Solvent effect on electronic absorption spectra of some N-aryl substituted dodekanamides

Viktorija Stamatovska, Vesna Dimova, Katica Čolančevska-Ragenoviќ

Abstract


A series of N-aryl substituted dodekanamides were synthesized using the reaction of fatty acid chloride (lauroylchloride) with p-substituted aromatic amines in the presence of triethylamine as an organic base and dioxane as a solvent. The structures of N-aryl substituted dodekanamides were determined by their melting temperature, IR and UV spectra. The ultraviolet absorption spectra of synthesized amides were recorded in seven polar solvents in the range from 200 nm to 400 nm. The effects of solvent polarity and of hydrogen bonding, on the absorption spectra, were interpreted by means of linear solvation energy relationships (LSER) using a general equation: ν = νo + sπ* + aα + bβ and by two-parameter models presented by the equation: ν = νo + sπ* + aα. The mode of influence of the solvent on the ultraviolet absorption spectra of the investigated dodekanamides are discussed on the basis of the correlation results.


Full Text:

PDF

References


A. L. J. Beckwith, in The Chemistry of Amides: Synthesis of Amides; J. Zabicky, ed. Interscience: New York, 1970, pp. 96–105.

M. Doležal, M. Miletin, R. Hejský, K. Králová, J. Kuneš, Synthesis of some amides of substituted pyrazine-2- carboxylic acids and their photosynthesis-inhibiting activity, International Electronic Conference on Synthetic Organic Chemistry

[C0009], September 1–30, 2001.

M. Doležal, M. Miletin, J. Kuneš, K. Králová, Substituted amides of pyrazine-2-carboxylic acids: synthesis and biological activity, Molecules, 7, 363–373 (2002).

B. Fabry, Surfactant mixtures comprising amides of fatty acids and N-methylglucamine and their use, (Henkel K.- G.a.A.) Ger. DE 4,400,632 (Cl. B01F17/22), 1995, 7 pp.

M. Tosaka, K. Ide, T. Hayase, Skin-compatible detergents containing alkyl glycosides and amide surfactants, (Kao Corp, Japan) Jpn. Kokai Tokkyo Koho JP 07, 310, 092

,310,092] (Cl. C11D1/835], 1995, 8 pp.

K. Kado, K. Matsushita, T. Fujii, K. Usuba, Surfactants based on polyoxyethylene fatty acid amides for detergents, (Kawaken Fine Chemicals Co; Takefu Fuain Kemikaru Kk) Jpn. KoKai Tokkyo Koho JP 07,102,292

,102,292] (Cl. C11D1/52), 1993, 13 pp.

Group of authors, Organikum, Nau na knjiga, Beograd, 1972, p. 391.

A. Kotera, S. Shibata, K. Sone, The dipole moments and near ultraviolet spectra of some compounds containing the CONH groups, J. Am. Chem. Soc., 77, 6183–6186 (1955).

S. Jing, J. Yanming, Y. Chaoguo, Substituent effect on UV spectra of 5-arylmethylenerhodanines, Chem. J. Internet, 3, 9–12 (2001).

C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 3nd Edition, Wiley-VCH, Weinheim, 2004, pp. 330–340.

M. J. Kamlet , R. W. Taft, The solvatochromic comparison metod. I. The -scale of solvent hydrogen-bond acceptor (HBA) basicities, J. Am. Chem. Soc., 98, 377–383 (1976).

M. J. Kamlet, R. W. Taft, The solvatochromic comparison metod. 2. The -scale of solvent hydrogen-bond donor (HBD) acidities, J. Am. Chem. Soc., 98, 2886–2894 (1976).

M. J. Kamlet, J. L. Abboud, R. W. Taft, The solvatochromic comparison metod. 6. The * scale of solvent solarities, J. Am. Chem. Soc., 99, 6027–6038 (1977).

N. V. Valenti , G. S. Uš umli , M. Radojkovi - Veli kovi , M. Miši -Vukovi , Solvent effects on electronic absorption spectra of 3-N-(4-substituted phenyl)-5- carboxy uracils, J. Serb. Chem. Soc. 64, 149–154 (1999).

J. B. Nikoli , G. S. Uš umli , V. V. Krsti , Solvent effects on electronic absorption spectra of cyclohex-1- enylcarboxylic and 2-methylcyclohex-1-enylcarboxylic acids, J. Serb. Chem. Soc. 65, 353–359 (2000).

D. Ž. Mijin, G. S. Uš umli , N. V. Valenti , Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 5-substituted-4-methyl-3-cyano-6- hydroxy-2-pyridones, J. Serb. Chem. Soc. 66, 507–516 (2001).

G. S. Uš umli , A. A. Kshad, D. Ž. Mijin, Synthesis and investigation of solvent effects on the ultraviolet absorption spectra of 1,3-bis-substituted-5,5-dimethylhydantoins, J. Serb. Chem. Soc. 68, 699–706 (2003).

K. Suganya, S. Kabilan, Substituent and solvent effects on electronic absorption spectra of some N-(substitutedphenyl) benzene sulphoamides, Spectrochimica Acta, Part A, 60, 1225–1228 (2004).

G. S. Uš umli , J. B. Nikoli , V. V. Krsti ,The reactivity of , -unsaturated carboxy acids. Part XVI. The kinetics of the reaction of cycloalkenylcarboxylic and cycloalkenylacetic acids with diazodiphenylmethane in various alcohols, J. Serb.Chem. Soc. 67, 353–359 (2002).

M. J. Kamlet, J. L. M. Abboud, M. H. Abraham, R. W. Taft, Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, *, , , and some methods for simplifying the generalized solvatochromic equation, J. Org. Chem., 48, 2877– 2887 (1983).


Refbacks

  • There are currently no refbacks.




Copyright (c) 2016 Viktorija Stamatovska, Vesna Dimova, Katica Čolančevska-Ragenoviќ

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.