Kinetics Study of the Formation of Pyrmidine Thione from the Reaction of 2,6-dibenzylidinecyclohexanone and its Derivatives with Thiourea
Abstract
Kinetics of the addition of thiourea to 2,6-dibenzylidenecyclohexanone and its derivatives have been studied. The reaction is found as a pseudo-first order process which includes a nucleophilic attack by thiourea at the carbonyl group of the ketone system to produce the heterocyclic pyrimidine thione "thiopyrimidine" (Claisen route mechanism). The effect of the substituents at the para position of the 2,6-dibenzylidenecyclohexanone and its derivatives on the rate of reaction, at different temperatures, is studied. Arrhenius parameters, entropies, enthalpies and free energies of activations are estimated. A suitable mechanism, which is correspondent with the results and with Claisen routes mechanism, is suggested for this reaction.
Downloads
References
Al-Hadithi, M.A., Al-Rawi, K.F., AL-Hity, W.F., 2007. Synthesis, Characterization and Kinetic studies of Some Oxazepine and Oxazepane Derivatives. J. of Al-Anbar University for Pure Science, 1(3), p.19 pages.
Al-Hamdany, A.J., Dabbagh, A.M. and Shareef, O.A., 2012. Synthesis of Spiropyrrolidines via 1, 3 Anionic Cycloaddition. Raf. J. Science, 23(3), pp.94-105.
Brown, H.C., Wheeler, O.H. and Ichikawa, K., 1957. ketones, Chemical effects of steric strains—XIII: Kinetics of the reaction of sodium borohydride with carbonyl groups—a convenient tool for investigating the reactivities of aldehydes. Tetrahedron, 1(3), pp.214-220.
Clayden J., Greeves N., Warren S. and Wothers P., 2001. Organic Chemistry. Oxford edition, pp.234-237.
Dabbagh, A.M., 2010. Chemical Kinetics. Baghdad (2263): University of mosul (Ibn Ether Publisher).
Dabbagh, A.M. and Al-Gwari, S.S., 2013. Kinetics and Mechanistic Studies of the Bromination of some Derivatives of 1,3-diaryl-2-propen-1-one. Raf. J. Science, 24(1), pp.50-59.
Dabbagh, A.M., Al-Hamdany, A.J. and Al-Sabawi, A.H., 2012. Kinetics and Mechanistic Studies of the Bromination of some Substituted 2-Benzylidene-1, 3-indandione. Raf. J. Sci., 23(4), pp.83-92.
Dabbagh, A.M., Al-Hamdany, A.J., Shareef, O.A. and Al-Assaf, S., 2012. Kinetic studies of the formation of number of spiropyrrolidines. Raf. J. Sci., 23(3), pp.58-77.
El-Ansary, A.K., Mohamed, N.A., Mohamed, K.O., Abd-Elfattah, H.M. and El-Manawaty, M., 2015. A Simple and Convenient Synthesis of Novel Thiopyrimidine Derivatives as Anticancer Agents. Research Journal of Pharmaceutical, Biological and Chemical Science, 6(4), pp.1745-1752.
Haji K.A., 2013. Kinetics and mechanistic studies on the formation of some chalcones in different solvents and their reactions with bromine and hydrazine, PhD Thesis, Erbil: Salahaddin University, pp.169-170.
Jihad T.W., 2011. Synthesis and Antibacterial Evaluation of Some New Fused Cyclic Sulfoxides. Raf. J. Sci., 22(4), pp.62-74.
Rajalakshmi K. and Ramachandramoorthy T., 2013. Oxidation of Chalcones by Morpholinium Chlorochromate with Oxalic Acid as Catalyst: Kinetic and Mechanistic Study. Journal of Chemistry, Hindawi Publishing Corporation, Vol. 2013, p.5 pages.
Copyright (c) 2016 Kosrat N. Kaka, Abdul Majeed M. Dabbagh, Wali M. Hamad
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.
Authors who choose to publish their work with Aro agree to the following terms:
-
Authors retain the copyright to their work and grant the journal the right of first publication. The work is simultaneously licensed under a Creative Commons Attribution License [CC BY-NC-SA 4.0]. This license allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
-
Authors have the freedom to enter into separate agreements for the non-exclusive distribution of the journal's published version of the work. This includes options such as posting it to an institutional repository or publishing it in a book, as long as proper acknowledgement is given to its initial publication in this journal.
-
Authors are encouraged to share and post their work online, including in institutional repositories or on their personal websites, both prior to and during the submission process. This practice can lead to productive exchanges and increase the visibility and citation of the published work.
By agreeing to these terms, authors acknowledge the importance of open access and the benefits it brings to the scholarly community.