Synthesis of New Series of Pyrazoline, and Study their Kinetics and Reaction Mechanism
A new series of novel pyrazoline compounds were synthesized by addition of thiosemicarbazide to the 2,6-dibenzylidenecyclohexanone (Chalcone) and its para substituted derivatives. This study was conducted for four purposes. Firstly, a series of five membered ring pyrazoline compounds were synthesized and the structure of all new products obtained are supported by spectral data (1H-NMR, 13CNMR, IR and UV-Vis.), and the effect of substituents were studied. Secondly, the reaction kinetics of the new synthesized compounds were studied to investigate the reaction mechanism pathway and order of the reaction; it was found that, the reaction undergoes via Claisen route of mechanism with first-order reaction. Thirdly, the thermodynamics of the reaction were studied, the rate of the reaction, Arrhenius parameters (A), and thermodynamic parameters for activation includes (free energies (Ea), entropies (ΔS#), and Gibbs free energy (ΔG#) were estimated. Finally, the compensation effect was also studied, and found the same pathway for all of the synthesized pyrazoline compounds.
Abdelhamid, A., Zohdi, H., Sallam, M., and Ahmed, N. 2000. Reactions with hydrazonoyl halides. 31. Synthesis of some new pyrrolidino [3, 4-c] pyrazolines, pyrazoles, and pyrazolo [3, 4-d] pyridazines. Molecules, 5, pp.967-973.
AL-Khayat, R.Z. 2010. PhD Thesis. University of Mosul.
Beyhan, N., Kocyigit-Kaymakcioglu, B., Gümrü, S., and Aricioglu, F. 2017. Synthesis and anticonvulsant activity of some 2-pyrazolines derived from chalcones. Arabian Journal of Chemistry, 10, pp.S2073-S2081.
Carey, F. 1996. Organic chemistry. McGraw-HiIl, New York, p.749.
Ceylan, M., and Gezegen, H. 2008. Preparation of 1, 5-diketones by addition of cyclohexanone to chalcones under solvent-free phase transfer catalyst condition. Turkish Journal of Chemistry, 32, pp.55-61.
Ebenezer, W., and Wight, P. 1995. In: Katrizky, A.R., Meth-Cohn, O., and Ress, C.W., editors. Comprehensive organic function group transfoamation. Vol. 3. Pergmon Press, Oxford, p.206.
Esmaeel, D.M.T. 1988. Organic chemistry. Directors are Publishing Houses, Mosul.
Ethiraj, K., Nithya, P., Krishnakumar, V., Mathew, A.J., and Khan, F.N. 2013. Synthesis and cytotoxicity study of pyrazoline derivatives of methoxy substituted naphthyl chalcones. Research on Chemical Intermediates, 39, pp.1833-1841.
Fazaeli, R., Aliyan, H., Bordbar, M., and Mohammadi, E. 2010. H3PW12O40: Highly efficient catalysts for the synthesis of novel 1, 3, 5-triaryl-2-pyrazoline derivatives. Open Catalysis Journal, 3, pp.79-82.
Gutsche, C.D. 1967. Chemistry of carbonyl compounds. Prentice-Hall, New Jersey.
Hamad, W.M., Kaka, K.N. Al-Hamadany, A.J., and Dabbagh, A.M. 2016. Synthesis and spectral characterization of some fused pyrimidine thiones. Journal Of Raparin University, 3, p.87.
Hassan, S.Y. 2011. Synthesis and biological activity of some new pyrazoline and pyrimidine derivatives. Journal of the Brazilian Chemical Society, 22, pp.1286-1298.
Joshi, V.D., Kshirsagar, M.D., and Sarita, S. 2012. Synthesis and antimicrobial activities of various pyrazolines from chalcones. International Journal of ChemTech Research, 4, pp.971-975.
Kaka, K., Dabbagh, A., and Hamad, W. 2016. Kinetics Study of the Formation of Pyrmidine Thione from the Reaction of 2, 6-Dibenzylidinecyclohexanone and its derivatives with Thiourea. ARO The Scientific Journal of Koya University, 4, pp.37-42.
Kaka, K.N. 2017. Kinetics and Mechanistics Studies on the Formation of 2,6-dibenzylidinecyclohexanones and their Reactions with Bromine, Hydrazine and Thiourea. Ph.D, Mosul.
Kendre, M., and Baseer, M. 2013. Synthesis and evaluation of some new pyrazoline derivatives as antimicrobial agents. Oriental Journal Chemistry, 29, pp.253-256.
Lévai, A. 2005. Synthesis of chlorinated 3, 5-diaryl-2-pyrazolines by the reaction of chlorochalcones with hydrazines. Arkivoc, 9, pp.344-352.
Li, J.T., Zhang, X.H., and Lin, Z.P. 2007. An improved synthesis of 1, 3, 5-triaryl- 2-pyrazolines in acetic acid aqueous solution under ultrasound irradiation. Beilstein Journal of Organic Chemistry, 3, p.13.
Mccrae, W. 1973. Basic organic reactions. Heyden and Son Ltd., London.
Monga, V., Goyal, K., Steindel, M., Malhotra, M., Rajani, D.P., and Rajani, S.D. 2014. Synthesis and evaluation of new chalcones, derived pyrazoline and cyclohexenone derivatives as potent antimicrobial, antitubercular and antileishmanial agents. Medicinal Chemistry Research, 23, pp.2019-2032.
Pandya, M., Kapadiya, K., Pandit, C., and Purohit, D. 2017. Synthesis of halogenated chalcones, pyrazolines and microbial evaluation of derived scaffolds. Journal of Scientific and Industrial Research, 76, pp.173-178.
Patel, M., Dodiya, B., Ghetiya, R., Joshi, K., Vekariya, P., Bapodara, A., and Joshi, H. 2011. Synthesis and antimicrobial evaluation of pyrazoline derivatives. International Journal ChemTech Research, 3, pp.967-974.
Powers, D.G., Casebier, D.S., Fokas, D., Ryan, W.J., Troth, J.R., and Coffen, D.L. 1998. Automated parallel synthesis of chalcone-based screening libraries. Tetrahedron, 54, pp.4085-4096.
Qiu, H., Sarkar, S.M., Lee, D.H., and Jin, M.J. 2008. Highly effective silica gel-supported N-heterocyclic carbene Pd catalyst for suzuki miyaura coupling reaction. Green Chemistry, 10, pp.37-40.
Ramage, G., Rodd, E., and Landquist, J. 1957. XVI. Chemistry of carbon compounds. IVC, heterocyclic compounds. Elsevier, New York.
Sloop, J.C., Lechner, B., Washington, G., Bumgardner, C.L., Loehle, W.D., and Creasy, W. 2008. Pyrazole formation: Examination of kinetics, substituent effects, and mechanistic pathways. International Journal of Chemical Kinetics, 40, pp.370-383.
Upadhyay, S.K. 2007. Chemical kinetics and reaction dynamics. Springer Science and Business Media, Berlin.
Copyright (c) 2019 Kosrat N. Kaka, Salam G. Taher, Wali M. Hamad, Aram H. Ibrahim
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License [CC BY-NC-SA 4.0] that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).