Iranian Journal of Chemistry

Iranian Journal of Chemistry

Theoretical investigation of the kinetics and reaction mechanism between triphenylphosphine and dimethyl acetylenedicarboxylate in the presence of 1-aminoanthraquinone as NH-acid

Document Type : Original Article

Authors
Ashraf Sadat ghasemi 1
Mohammad Zakarianezhad 2
Batoul Makiabadi 3
1 َAssictant Professor Department of Chemistry, Payame Noor University, Tehran, Iran.
2 هیئت علمی
3 Associate Professor-Physical Chemistry Department of Chemical Engineering, Sirjan University of Technology
10.22036/cr.2021.292513.1150
Abstract
In this study, the reaction mechanism between dimethyl acetylene, dicarboxylate and triphenylphosphine in the presence of 1-aminoanthraquinone as NH-acid was examined theoretically using the method B3lyp / 6-311++G(d, p):HF/6-31G. According to the theoretical results, a logical mechanism for the reaction was proposed and the most desirable reaction path for the product was predicted. In the present work, the reaction between a kinetic study, including determining the preferred kinetic path, investigation of intermediate structures and transition states in the reaction path, determination of the kinetic and thermodynamic stability of products, recognition of rate-determining step, calculation of the reaction rate, and finally, identifying and confirming the reaction mechanism are the issues that have been first explored for this reaction. To check the effect of solvent on the potential energy surfaces, condensed phase calculations in dichloroethane were carried out with the polarizable continuum model (PCM). Finally, in order to better understand molecular interactions, the natural graft orbital method (NBO) was used.

Graphical Abstract

Theoretical investigation of the kinetics and reaction mechanism between triphenylphosphine and dimethyl acetylenedicarboxylate in the presence of 1-aminoanthraquinone as NH-acid
Keywords
Theoretical study
Phosphorus Ylide
NH-acid
E- and Z-isomers
NBO
  1. A. K. Corbridge, W. A. Goddard III, J. Phys. Chem. 95, 3358 (1995).
  2. S.Contorno, R. E.Darienzo, R. Tannenbaum, Scientific Reports. 11,1698 (2021).
  3. P. L. A. Rostami, Atoms in molecules. An introduction, Prentice, Pearson Education. Essex. England. 2011.

[4] 4. A. Ramazani, N. Shajari, A .Tofangchi Mahyari, M Khoobi, Y. Ahmadi, A. Souldozi, Phosphorus Sulfur Silicon Relat. Elem. 185, 2496 (2010).

  1. H. S. Kalantari, R. Graham, J. Chem. 52, 1415 (2006).
  2. S. M. Habibi Khorassani, M. T. Maghsoodlou, A. Ebrahimi, H. Roohi, M. Zakarianezhad, M. Moradian, Progress in Reaction Kinetics and Mechanism. 30, 127 (2005)
  3. M. Feyzi, L. Nourozi, M. Zakarianezhad, Materials Research Bulletin. 60, 412 (2014).
  4. H. R. Masoodi, S. Bagheri, M. Mohammadi, M. Zakarianezhad, B. Makiabadi, Chemical Physics Letters. 588, 31 (2013).
  5. M. Zakarianejad, H. Ghasempour, S. M. Habibi-Khorassani, M. T. Maghsoodlou, B. Makiabadi,M. Nassiri, Z. Ghahghayi, A. Abedi, Arkivoc. 2013, 171 (2013).
  6. H. Roohi, B. Mackiabadi, Bulletin of the Chemical Society of Japan. 80, 1914 (2007).
  7. B. Makiabadi, H. Kian, Monatshefte fur Chemie. 146, 69 (2015).
  8. M. Zakarianezhad, S. M. Habibi-Khorassani, M. T. Maghsoodlou, B. Makiabadi, Oriental Journal of Chemistry. 28, 1259 (2012).
  9. H. R. Masoodi, M. Zakarianezhad, S. Bagheri, B. Makiabadi, M. Shool, Chemical Physics Letters. 614, 143 (2014).
  10. S. M. H. Khorassani, M. T. Maghsoodlou, H. Ghasempour, M. Zakarianezhad, M. Nassiri, Z.Ghahghaie, Journal of Chemical Sciences. 125, 387 (2013).
  11. M. Zakarianezhad, B. Makiabadi, S. M. Habibi-Khorassani, M. Shool, M. Eslamlou, Researchon Chemical Intermediates. 44, 2653 (2018).
  12. S. M. Habibi-Khorassani, B. Adrom, Z. Gharechahi, M. T. Maghsoodlou, R. Heydari, M. Ghahramaninezhad, R. Kabiri, G. Marandi, Phosphorus, Sulfur, and Silicon, 185, 1395 (2010).
  13. M. Frisch, G. Trucks, H. B. Schlegel, G. Scuseria, M. Robb, J. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. Petersson, Gaussian 09, Revision A. 02, Gaussian. Inc, Wallingford, CT, 2009.
  14. A. M.Verma, N. Kishore, ChemistrySelect. 2, 1556 (2017).
  15. C. Gonzalez, H. B. Schlegel, J Phys Chem. 94, 5523 (1990).
  16. C. Gonzalez, H. B. Schlegel, J Chem Phys. 90, 2154 (1989).
  17. K. M. Al-Ahmary, M. M. Habeeb, S. H. Aljahdali, Journal of Molecular Liquids, 277, 453 (2019).
  18. E. Cances, B. Mennucci, J. Tomasi, J Chem Phys. 107, 3032 (1997).
  19. M. Cossi, V. Barone, R. Cammi, J. Tomasi, Chem Phys Lett. 255, 327 (1996).
  20. D. E. Glendening, A. E. Reed, J. E. Carpenter, F. Weinhold, NBO, Version 3.1.
  21. F. Biegler-Knig, J. Schnbohm, D. Bayles, J Comput Chem. 22, 545 (2001).
  22. H. Ghasempour, M. Zakarianezhad, B. Makiabadi, S. M. Habibi-Khorassani Iranian Journal of Science and Technology, Transaction A: Science. 40, 255 (2016).
  23. M. Zakarianezhad, B. Makiabadi, S. S. Hosseini, Theoretical Chemistry Accounts. 140, 214 (2021).
  24. S. M. Habibi Khorassani, M. T Maghsoodlou, A. Ebrahimi, H. Roohi, M. Zakarianezhad, H. R. Dasmeh, M.Moradian, Phosphorus, Sulfur and Silicon and the Related Elements. 181, 1103 (2006).
  25. M. Zakarianezhad, B. Makiabadi, M. Shool, Journal of the Chilean Chemical Society. 61, 2929 (2016).
  26. M. Zakarianezhad, B. Makiabadi, P. Sotoodeh, E. Zeydabadi, Phosphorus, Sulfur and Silicon and the Related Elements. 28, 656 (2021).
  27. M. Zakarianezhad, S. M. Habibi-Khorassani, M. T. Maghsoodlou, B. Makiabadi, H. Ghasempour, Iranian Journal of Science and Technology, Transaction A: Science. 36, 251 (2012).
  28. K. A. Conors, Chemical Kinetics–The Study of Reaction Rate in Solution, Wiley, New York, 1990.
  29. D. G. Truhlar, B. C. Garrett, S. J. Klippenstein, J. Phys. Chem. 100, 12771 (1996).

 

 

Iranian Journal of Chemistry
Volume 4, Issue 2 - Serial Number 7
February 2022
Pages 155-162

  • Receive Date 27 June 2021
  • Revise Date 30 September 2021
  • Accept Date 06 October 2021