Introducción a la interpretación de Ciclos Catalíticos: una metodología sencilla para estudiantes universitarios de segundo año

Contenido principal del artículo

Itzel Guerrero-Ríos
Iván Darío Rojas-Montoya
Antonio Reina Tapia

Resumen

El conteo de electrones y la regla de los 18 electrones son herramientas importantes para la comunidad académica porque ofrecen información valiosa sobre un compuesto de coordinación, en particular para predecir su estabilidad y reactividad catalítica. En este trabajo, presentamos una metodología algebraica de fácil aplicación basada en el método de conteo covalente que permite al estudiante contar electrones mediante ecuaciones matemáticas. Además, proporciona información adicional sobre el compuesto de coordinación, incluyendo el número de electrones de valencia, el número de coordinación, el estado de oxidación y el número de electrones no enlazantes. A lo largo del manuscrito, mostramos cómo estos cuatro parámetros son útiles para reconocer los pasos elementales en catálisis, y se proporciona un árbol de decisiones para hacerlo. Finalmente, presentamos una metodología para interpretar ciclos catalíticos. Esta actividad se probó con más de 150 estudiantes de la Facultad de Química de la UNAM, con resultados alentadores en cuanto al conocimiento adquirido en el conteo de electrones e interpretación de ciclos catalíticos. Por lo tanto, creemos firmemente que esta estrategia puede ser muy útil para estudiantes universitarios, docentes e investigadores.

Detalles del artículo

Biografía del autor/a

Antonio Reina Tapia, Universidad Nacional Autónoma de México, UNAM

Departamento de Química Inorgánica y Nuclear, Facultad de Química

Citas

Ahmad, W.-Y.; Omar, S. Drawing Lewis structures: A step-by-step approach. J. Chem. Educ., 1992, 69(10), 791-792. https://doi.org/10.1021/ed069p791

Ahmad, W.-Y.; Zakaria, M. B. Drawing Lewis Structures from Lewis Symbols: A Direct Electron-Pairing Approach. J. Chem. Educ., 2000, 77(3), 329-331. https://doi.org/10.1021/ed077p329

Astruc, D. Organometallic Chemistry and Catalysis, Springer, Berlin, 2007, 37-41.

Bhadari, S.; Mukesh, D. Homogeneous Catalysis: Mechanisms and Industrial Applications. Wiley, 2014.

Bochmann M. Organometallics and Catalysis an Introduction, Oxford University Press, New York, 2015.

Brady, J. A.; Milbury-Steen, J. N.; Bureister, J. L. Lewis structure skills: Taxonomy and difficulty levels. J. Chem. Educ., 1990, 67(6), 491-493. https://doi.org/10.1021/ed067p491

Catlow, C. R.; Davidson, M.; Hardacre, C.; Hutchings, G. J. Catalysis making the world a better place. Phil. Trans. R. Soc. A, 2015, 374, 20150089. https://doi.org/10.1098/rsta.2015.0089

Chalk, A. J.; Harrod, J. F. Homogeneous Catalysis. II. The Mechanism of the Hydrosilation of olefins Catalyzed by Group VIII Metal Complexes. J. Am. Chem. Soc., 1965, 87(1), 16-21. https://doi.org/10.1021/ja01079a004

Crabtree, R. H.; Mingos, D. M. P. Comprehensive Organometallic Chemistry III, Volume 1, Chapter 1; Elsevier, Oxford, 2007.

Delolo, F. G.; Yang, J.; Neumann, H.; dos Santos, E. N.; Gusevskaya, E. V.; Beller, M. Cobalt-Catalyzed Hydroformylation under Mild Conditions in the Presence of Phosphine Oxides. ACS Sustainable Chem. Eng., 2021, 9, 5148-5154. https://doi.org/10.1021/acssuschemeng.1c00205

Duncan, A. P.; Johnson, A. R. A “Classic Papers” Approach to Teaching Undergraduate Organometallic Chemistry. J. Chem. Educ., 2007, 84(3), 443-446. https://doi.org/10.1021/ed084p443

Elschenbroich C.; Salzer A. Organometallic: a Concise Introduction, VCH, Weinheim, 1992.

Green, M. L.-H. A new approach to the formal classification of covalent compounds of the elements. J. Organomet. Chem., 1995, 500, 127-148. https://doi.org/10.1016/0022-328X(95)00508-N

Green, M. L.-H.; Parkin, G. Application of the Covalent Bond Classification Method for the Teaching of Inorganic Chemistry. J. Chem. Educ., 2014, 91(6), 807-816. https://doi.org/10.1021/ed400504f

Hartwig, J. F. Organotransition Metal Chemistry: From Bonding to Catalysis, University Science Books, Sausalito, 2010.

Housecroft, C. E.; Sharpe, A. J. Inorganic Chemistry (Chapter 4), Pearson, Harlow, 2012.

Jackson, B. A.; Harshman, J.; Miliordos, E. Addressing the Hypervalent Model: A Straightforward Explanation of Traditionally Hypervalent Molecules. J. Chem. Educ., 2020, 97(10), 3638-3646. https://doi.org/10.1021/acs.jchemed.0c00368

Jensen, W. B. Abegg, Lewis, Langmuir, and the octet rule. J. Chem. Educ., 1984, 61(3), 191-200. https://doi.org/10.1021/ed061p191

Jensen, W. B. The Origin of the 18-electron rule. J. Chem. Educ., 2005, 82(1), 28. https://doi.org/10.1021/ed082p28

Joki, J.; Aksela, M. The challenges of learning and teaching chemical bonding at different school levels using electrostatic interactions instead of the octet rule as a teaching model. Chem. Res. Educ. Pract., 2018, 19, 932-953. https://doi.org/10.1039/C8RP00110C

Langmuir, I. Types of Valence, Science, 1921, 54, 59-67. Reprinted in Suits, C. G., Ed., The Collected Works of Irving Langmuir, Vol. 6, Pergamon, New York, 1961, pp. 128-139.

Lever, A. B. P. Lewis structures and the octet rule. An automatic procedure for writing canonical forms. J. Chem. Educ., 1972, 49(12), 819-821. https://doi.org/10.1021/ed049p819

McArdle, P. Systematic Procedure for Drawing Lewis Structures Based on Electron Pairing Priority and the Explicit Use of Donor Bonds: An Alternative to the Normal Procedure Which Can Be Pen and Paper Based or Automated on a PC in User Interactive 3D. J. Chem. Educ., 2019, 96(7), 1412-1417. https://doi.org/10.1021/acs.jchemed.8b00868

Mingos, D. M. P. Complementary spherical electron density model and its implications for the 18 electron rule. J. Organomet. Chem., 2004, 689, 4420-4436. https://doi.org/10.1016/j.jorganchem.2004.07.020

Miessler, G. L.; Spessard, G. O. Organometallic Chemistry: A Course Designed for Sophomore Chemistry Students, J. Chem. Educ., 1991, 68(11), 16-19. https://doi.org/10.1021/ed068p16

Mitchell, P. R.; Parish, R. V. The Eigtheen-Electron Rule, J. Chem. Educ., 1969, 46(12), 811-814. https://doi.org/10.1021/ed046p811

Nassif, P.; Czerwinski, W. A. Teaching Beginning Chemistry Students Simple Lewis Dot Structures. J. Chem. Educ., 2015, 92(8), 1409-1411. https://doi.org/10.1021/ed5007162

Powell, P. Principles in Organometallic Chemistry, Springer, Berlin, 1998.

Rasmussen, S. C. The 18-electron rule and electron counting in transition metal compounds: theory and application, ChemTexts, 2015, 1, 10. https://doi.org/10.1007/s40828-015-0010-4

Reina, A.; García-Ortega, H.; Gracia-Mora, J.; Marín-Becerra, A.; Reina, M. CADMIO: Creating and Curating an Educational YouTube Channel with Chemistry Videos, J. Chem. Educ., 2021, 98(11), 3593-3599. https://doi.org/10.1021/acs.jchemed.1c00794

Reina, M.; Guerrero-Ríos, I.; Reina, A. The Study of Metal–Carbonyl Complexes by Means of Computational IR Spectra Analysis: A Remote Didactic Approach Based on Chemical Thinking. J. Chem. Educ., 2022, 99(9), 3211-3217. https://doi.org/10.1021/acs.jchemed.2c00577

Reisner, B. A.; Stewart, J. L.; Williams, B. S.; Goj, L. A.; Holland, P. L.; Eppley, H. J.; Johnson, A. R. Virtual Inorganic Pedagogical Electronic Resource Learning Objects in Organometallic Chemistry. J. Chem. Educ., 2012, 89, 185-187. https://doi.org/10.1021/ed200200w

Schaller, C. P.; Graham, K. J.; Johnson, B. J. Modules for Introducing Organometallic Reactions: A Bridge between Organic and Inorganic Chemistry. J. Chem. Educ., 2015, 92, 986-992. https://doi.org/10.1021/ed500817m

See, R. F. Which Method of Assigning Bond Orders in Lewis Structures Best Reflects Experimental Data? An Analysis of the Octet Rule and Formal Charge Systems for Period 2 and 3 Nonmetallic Compounds. J. Chem. Educ., 2009, 86(10), 1241-1247. https://doi.org/10.1021/ed086p1241

Semba, K.; Nakao Y. Arylboration of Alkenes by Cooperative Palladium/Copper Catalysis. J. Am. Chem. Soc., 2014, 136(21), 7567-7570. https://doi.org/10.1021/ja5029556

Shao, Z.; Zhang, H. Combining Transition Metal Catalysis and Organocatalysis: a Broad New Concept for Catalysis. Chem. Soc. Rev., 2009, 38(9), 2745−2755. https://doi.org/10.1039/B901258N

Spessard G. O.; Miessler G. L. Organometallic Chemistry, Oxford University Press, New York, 2010.

Straub, D. K. Lewis Structures of Oxygen Compounds of 3p-5p Nonmetals. J. Chem. Educ., 1995, 72(10), 889-891. https://doi.org/10.1021/ed072p889

Tolman, C. A. The 16- and 18-electron rule in organometallic chemistry and homogeneous catalysis, Chem. Soc. Rev., 1972, 1, 337-353. https://doi.org/10.1039/CS9720100337

Van Leuwen, P. W. N. M. Homogeneous Catalysis, Kluwer Academic Publishers, Dordrecht, 2004.

Zandler, M. E.; Talaty, E. R. The "6N+2 Rule" for writing Lewis octet structures. J. Chem. Educ., 1984, 61(2), 124-127. https://doi.org/10.1021/ed061p124

Zoeller, J. R.; Agreda, V. H.; Cook, S. L.; Lafferty, N. L.; Polichnowski, S. W.; Pond, D. M. Eastman Chemical Company Acetic Anhydride Process. Catal. Today, 1992, 13, 73-91. https://doi.org/10.1016/0920-5861(92)80188-S