Solvent effect on the kinetics of nucleophilic addition of hydroxide ion to triphenylmethane dyes
Abstract
Spectrophotometric method has been used for the determination of the rate constants of reactions of nucleophilic addition of hydroxide ion to ions of certain triphenylmethane dyes: dinitrophenolsulfophtalein, tetranitrophenolsulfophalein, phenolphthalein, acid fuchsin and crystal violet in a mixed aqueous–organic solvents containing ethanol, acetone or acetonitrile. It has been determined that the solvent effects on the rate of the reactions are generally consistent with the Hughes-Ingold rule. Quantitative treatment of the rate constants dependence was carried out by Scatchard equation that takes into account only the influence of the dielectric constant of the solvent, as well as the principle of the linear solvation energy relationships (LSER), taking into account Reichardt or Kamlet–Taft solvatochromic parameters of solvent polarity. Results of calculations show that the using of the solvent dielectric constant (DC) only is not sufficient for the describing of the kinetic effect of the mixed solvent composition. This is observed because DC takes into account only nonspecific solvation. It has been found that the dependences of the rate constants are satisfactorily described by the correlation equations based on the LSES principle. An analysis of the coefficients of these equations shows that the influence of the mixed solvent composition on the reaction rate is mainly determined by the contribution of the specific solvation.
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Reichardt C., Welton T. Solvents and solvent effects in organic chemistry. 4th ed. WILEY-VCH, 2011. 692 p.
Amis E. S., La Mer V. K. // J. Am. Chem. Soc. 1939. Vol.61, No.4. P.905–913.
Amis E. S., Price J. B. // J. Phys. Chem. 1943. Vol.47, No.4. P.338–348.
Quinlan J. E., Amis E. S. // J . Am. Chem. Soc. 1955. Vol.71, No.16. P.4187–4191.
Katiyar S. S. // Trans. Faraday Soc. 1970. Vol.66. P.2305–2312.
Fathalla M. F. // J. Solut. Chem. 2011. Vol.40, No.7. P.1258–1270.
Ghosh K. K., Patle S. K. // Indian J. Chem. 2002. Vol.41A. P.758–762.
Bhuvaneshwari D. S., Elango K. P. // International J. Chem. Kinetics. 2007. Vol.39. No.12. P.657–663.
Katritzky A. R., Fara D. C., Yang H., Tamm K. // Chem. Rev. 2004. Vol.104, No.1. P.175 198.
Marcus Y. // Chem. Soc. Rev. 1993. Vol.22, No.6. P.409–416.
Berezin I. V., Martinek K., Yatsimirskiy A. K. // Uspehi khimii. 1973. Vol.52, No.10. P.1729 1756. [in Russian]
Buurma N. J. Kinetic medium effects on organic reactions in aqueous colloidal solutions. //Adv. Phys. Org. Chem. Academic Press, 2009. Vol.43. P.1–37.
Mchedlov-Petrossyan N. O., Roshchyna K. V., Shekhovtsov S. V., Eltsov S. V., Zozulia O. S., Omelchenko I. V., Shishkin O. V. // Color. Technol. 2015. Vol.131. P.1–9.
Armarego W. L. F., Christina C. L. L. Purification of laboratory chemicals, 7 th ed. Elsevier, 2013.1002 p.
Duynstee E. F. G., Grunwald E. // J. Am. Chem. Soc. 1959. Vol.81, No.17. P.4540–4542.
Roshchina E.V., Eltsov S.V., Mchedlov-Petrossyan N. O. // Ukrain. Chem. J. 2013. Vol.79, № 9. С.25–30. (In Russian)
Samiey B., Dalvand Z. // Int. J. Chem. Kinet. 2014. Vol.46, No.1. P.60–70.
Samiey B., Dalvand Z. // Int. J. Chem. Kinet. 2014. Vol.46, No.11. P.651–661.
Roshchyna K. V., Eltsov S. V., Laguta A. N., Mchedlov-Petrossyan N. O. // J. Molecular Liq-uids. 2015. Vol.201. P.77–82.
Chen D. T. Y., Laidler K. J. // Can. J. Chem. 1959. Vol.37, No.3. P.599–642.
Mao Sh., Chen Zh., An X., Shen W. // J. Phys. Chem A. 2011. Vol.115, No.22. P.5560–5567.
Laguta A. N., Eltsov S. V. // Visn. Hark. nac. univ. 2013. №1085. Ser. Him. Issue 22 (45). P.127–135. (In Russian)
Laguta A. N., Eltsov S. V. // Visn. Hark. nac. univ. 2014. №1136. Ser. Him. Issue 24 (47). P.19–30. (In Russian).
Panichajakul C. C., Woolley E. M. // Anal. Chem. 1975. Vol. 47, No.11. P.1861–1863.
Gutbezahl B. B., Grunwald E. // J. Am. Chem. Soc. 1953. Vol.75, No.3. P.565–574.
Mandal U., Sen S,. Das K,. Kundu K.K. // Can. J. Chem. 1986. Vol.64, No.2. P.300–307.
Afanasyev V. N. Efremova L. S., Volkova Т. V. Physico-chemical properties of the binary solvent. Aqueous-based systems. Part I. Ivanovo, 1988. 216 р. (In Russian).
Marcus Y. // J. Chem. Soc., Perkin Trans. 2. 1994. Vol.5. P.1015–1021.
Marcus Y. // J. Chem. Soc., Perkin Trans. 2. 1994. Vol.8. P.1571–1758.
Reichardt C. // Chem. Rev. 1994. Vol.94, No.8. P.2319–2358.
Ghosh K. K., Satnami M. L., Sinha D., Vaidya J. // J. Molecular Liquids. 2005. Vol.116. P.55–60.
Kamlet M. J., Abboud J. L. M., Abraham M. H., Taft R. W. // J. Org. Chem. 1983. Vol.48, No.17. P. 2877–2887.
Reichardt C. // Pure Appl. Chem. 1982. Vol.54, No.10. P.1867–1884.
Park J. H., Jang M. D., Kim D. S., Carr P. W. // J. Chromatogr. 1990. Vol.513. P.107–116.
Schneider H., Badrieh Y., Migron Y., Marcus Y. // Z. Phys. Chem. 1992. Bd.177. S.143–156.
Marcus Y., Migron Y. // J. Phys. Chem. 1991. Vol.95, No.1. P.400–406.
Krygowski T. M., Wrona P. K., Zielkowska U., Reichardt C. // Tetrahedron. 1985. Vol.41, No.20. P.4519–4527.
Citations
Kinetics of alkaline fading of methyl violet in micellar solutions of surfactants: Comparing Piszkiewicz's, Berezin's, and pseudophase ion-exchange models
Laguta Anna N., Eltsov Sergey V. & Mchedlov-Petrossyan Nikolay O. (2019) International Journal of Chemical Kinetics
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