Abstract
The reaction between piperazine and benzyl bromide was studied conductometrically and the second order rate constants were computed. These rate constants determined in 12 different protic and aprotic solvents indicate that the rate of the reaction is influenced by electrophilicity (E), hydrogen bond donor ability (α) and dipolarity/polarizability (π*) of the solvent. The LSER derived from the statistical analysis indicates that the transition state is more solvated than the reactants due to hydrogen bond donation and polarizability of the solvent while the reactant is more solvated than the transition state due to electrophilicity of the solvent. Study of the reaction in methanol, dimethyl formamide mixtures suggests that the rate is maximum when dipolar interactions between the two solvents are maximum.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Fawcett W R and Krygowski T M 1975 Aust. J. Chem. 28 2115
Ballistreri F F, Maccarone E, Masumurra G and Towasell G A 1977 J. Org. Chem. 42 1415
Reichardt C 1979 Angew. Chem. Int. Ed. Engl. 18 98
Krygowski T M, Radomski J P, Rzeszowiak A and Wrona P K 1981 Tetrahedron 37 119
Manikyamba P and Sundaram E V 1990 Int. J. Chem. Kinetics 22 1153
Manikyamba P 1996 Indian J. Chem. A35 334
Koppel I A and Palm V A 1972 Advances in linear free energy relationships (eds) N V Chapman and J Shorter (New York: Plenum Press) p 222
Gholami M R and Habibi Yangjeh A 2000 Int. J. Chem. Kinetics 32 118
Marcus Y 1994 J. Chem. Soc. Perkin Trans II 1015
Skwierczynski D and Connors K A 1994 J. Chem. Soc. Perkin Trans II 467
Roses M, Rafols C, Ortega J and Bosch E 1995 J. Chem. Soc. Perkin Trans II 1607
Frost A A and Pearson R G 1970 Kinetics and mechanism (New Delhi: Wiley Eastern) 2nd edn, p 37
Nakanishi K and Solomon P H 1977 Infrared absorption spectroscopy (Holden-Day) p 50
Aslam M H, Collier G and Shorter J 1981 J. Chem. Soc. Perkin Trans II 1572
Koppel I A and Paju A I 1974 Org. React. (Tarter). 11 137
Taft R W, Abboud J L M, Kamlet M J and Abraham M H 1983 J. Org. Chem. 48 2877
Shorter J 1982 Correlation analysis of organic reactivity (Research Studies Press: John Wiley and Sons) p 107
Ezekiel M and Fox K A 1959 Methods of correlation and regression analysis (New York: Wiley) 3rd edn
Jones R A Y 1979 Physical and mechanistic organic chemistry (Cambridge University Press) p 87
Bakshi M S, Singh J and Kaur H 1996 J. Chem. Engg. Data 41 1459
Bakshi M S and Gurinder Kaur 1997 J. Chem. Engg. Data 42 298
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ranga Reddy, S., Manikyamba, P. Solvent effects in the reaction between piperazine and benzyl bromide. J Chem Sci 119, 613–616 (2007). https://doi.org/10.1007/s12039-007-0076-7
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12039-007-0076-7