Skip to main content
Springer Nature Link
Log in

Performance of DFT and MP2 Approaches for Geometry of Rhenium Allenylidenes Complexes and the Thermodynamics of Phosphines Addition

  • Conference paper
Computational Science and Its Applications – ICCSA 2012 (ICCSA 2012)

Part of the book series: Lecture Notes in Computer Science ((LNTCS,volume 7333))

Included in the following conference series:

  • 2070 Accesses

Abstract

The performance of density functional theory (DFT) and Møller-Plesset perturbation second order theory (MP2) for prediction of the geometry of an important class of rhenium complexes and the thermodynamics of their reaction with nucleophiles has been assessed. In particular, we addressed the rhenium(I) allenylidene [(triphos)(CO)2Re(=C=C=CPh2)] +  species [triphos = MeC(CH2PPh2)3] and its reaction toward tertiary phosphines. Several exchange-correlation functionals were tested and the results indicate that the usually employed GGA and hybrid functionals, such a BP86, BLYP, B3LYP and PBE while correctly predicting the geometry of these species, qualitatively and quantitatively fail to reproduce the thermodynamics for the addition of the phosphine nucleophiles, especially the first three ones, with errors up to 30 kcal mol− 1. Reasonable results, qualitatively in agreement with experimental evidence, can be obtained only through the use of a correlated wavefunction approach such as MP2 or of the more recently developed functionals M06 and M06-L.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Similar content being viewed by others

References

  1. Steinborn, D.: Fundamentals of organometallic catalysis. Wiley-VCH, Weinheim (2012)

    Google Scholar 

  2. Hartwig, J.: Organotransition metal chemistry: from bonding to Catalysis. University Science Books, Sausalito (2010); Sautet, P., Delbecq, F.: Chem. Rev. 110, 178 (2010)

    Google Scholar 

  3. Jiang, W., De Yonker, N.J., Determan, J.J., Wilson, A.K.: J. Phys. Chem. A 116, 870 (2012)

    Article  Google Scholar 

  4. Quintal, M.M., Karton, A., Iron, M.A., Daniel Boese, A., Martin, J.M.L.: J. Phys. Chem. A 110, 709 (2006); Harvey, J.N.: Annu. Rep. Prog. Chem., Sec. C: Phys. Chem. 102, 203 (2006)

    Google Scholar 

  5. Wodrich, M.D., Corminboeuf, C., von Ragué Schleyer, P.Y., Truhlar, D.: Org. Lett. 8, 3631 (2006); Zhao, Y., Truhlar, D.G.: J. Phys. Chem. A 110, 10478–10486 (2006); Grimme, S., Steinmetz, M., Korth, M.: J. Chem. Theory Comput. 3, 4245 (2007)

    Google Scholar 

  6. Fomine, S., Tlenkoplatchev, M.A.: Organometallics 26, 4491 (2007); Sieffert, N., Büehl, M.: Inorg. Chem. 48, 4622 (2009)

    Google Scholar 

  7. Sliwa, P., Handzlik, J.: Chem. Phys. Lett. 493, 273 (2010); Zhao, Y., Dutta, B.F.E., Curchod, B., Campomanes, P., Solari, E., Scopelliti, R., Rothlisberger, U., Severin, K.: Chem. Eur. J. 16, 8400 (2010); Kulkarni, A.D., Truhlar, D.G.: J. Chem. Theory Comput. 7, 2325 (2011)

    Google Scholar 

  8. Coletti, C., Gonsalvi, L., Guerriero, A., Marvelli, L., Peruzzini, M., Reginato, G., Re, N.: Organometallics 29, 5982 (2010)

    Article  Google Scholar 

  9. Coletti, C., Gonsalvi, L., Guerriero, A., Marvelli, L., Peruzzini, M., Reginato, G., Re, N.: Organometallics 31, 57 (2012)

    Article  Google Scholar 

  10. Bruce, M.I.: Chem. Rev. 98, 2797 (1998); Rigaut, S., Touchard, D., Dixneuf, P.H.: Coord. Chem. Rev. 248, 1585–1601 (2004); Cadierno, V., Gimeno, J.: Chem. Rev. 109, 3512 (2009)

    Google Scholar 

  11. Touchard, D., Dixneuf, P.H.: Coord. Chem. Rev. 409, 178–180 (1998); Bruneau, C., Dixneuf, P.H.: Acc. Chem. Res. 32, 311 (1999); Buil, M.I., Esteruelas, M.A., López, A.M., Oñate, E.: Organometallics 22, 162 (2003); Bruneau, C., Dixneuf, P.H. (eds.) Metal Vinylidenes and Allenylidenes in Catalysis: From Reactivity to Applications in Synthesis. Wiley-VCH, Weinheim (2008)

    Google Scholar 

  12. Abdallaoui, I.A., Sémeril, D., Dixneuf, P.H.: J. Mol. Catal. A: Chem., 182–183, 577 (2002); Akiyama, R., Kobayashi, S.: Angew. Chem., Int. Ed. 41, 2602 (2002); Bruneau, C., Dixneuf, P.H.: Angew. Chem., Int. Ed. 45, 2176–2203 (2006)

    Google Scholar 

  13. Bunz, U.H.F.: Angew. Chem., Int. Ed. Engl. 35, 969 (1996); Roth, G., Fischer, H., Meyer-Friedrichsen, T., Heck, J., Houbrechts, S., Persoons, A.: Organometallics 17, 1511–1516 (1998); Dembiski, R., Bartik, T., Bartik, B., Jaeger, M., Gladysz, J.A.: J. Am. Chem. Soc. 122, 810 (2000)

    Google Scholar 

  14. Marrone, A., Re, N.: Organometallics 21, 3562 (2002); Marrone, A., Coletti, C., Re, N.: Organometallics 23, 4952 (2004); Auger, N., Touchard, D., Rigaut, S., Halet, J.-F., Saillard, J.-Y.: Organometallics 22, 1638 (2003); Coletti, C., Marrone, A., Re, N.: Acc. Chem. Res. 45, 139 (2012)

    Google Scholar 

  15. Mantovani, N., Marvelli, L., Rossi, R., Bianchini, C., de los Rios, I., Romerosa, A., Peruzzini, M.: J. Chem. Soc., Dalton Trans., 2353 (2001)

    Google Scholar 

  16. Peruzzini, M., Barbaro, P., Bertolasi, V., Bianchini, C., de los Rios, I., Mantovani, N., Marvelli, L., Rossi, R.: J. Chem. Soc., Dalton Trans., 4121 (2003); Mantovani, N., Bergamini, P., Marchi, A., Marvelli, L., Rossi, R., Bertolasi, V., Ferretti, V., de los Rios, I., Peruzzini, M.: Organometallics 25, 416 (2006)

    Google Scholar 

  17. Zhao, Y., Truhlar, D.: Theor. Chem. Acc. 120, 215 (2008); Truhlar, D.G.: Acc. Chem. Res. 41, 157 (2008)

    Google Scholar 

  18. Jaguar 7.5. Schrödinger, LLC, New York, NY (2007)

    Google Scholar 

  19. Becke, A.D.: Phys. Rev. A 38, 3098 (1988); Perdew, J.P.: Phys. Rev. B 33, 8822 (1986)

    Google Scholar 

  20. Lee, C., Yang, W., Parr, R.G.: Phys. Rev. B 37, 785 (1988)

    Article  Google Scholar 

  21. Perdew, J.P., Burke, K., Enzerhof, M.: Phys. Rev. Lett. 67, 3865 (1996)

    Article  Google Scholar 

  22. Becke, A.D.: J. Chem. Phys. 98, 5648 (1993); Lee, C.T., Yang, W.T., Parr, R.G.: Phys. Rev. B 37, 785 (1988)

    Google Scholar 

  23. Zhao, Y., Truhlar, D.G.: J. Chem. Phys. 125, 194101 (2006)

    Article  Google Scholar 

  24. Hehre, W.J., Ditchfield, R., Pople, J.A.: J. Chem. Phys. 56, 22567–2261 (1972)

    Google Scholar 

  25. Hay, P.J., Wadt, W.R.: J. Chem. Phys. 82, 270, 284, 299 (1985)

    Google Scholar 

  26. Krishnan, R., Binkley, J.S., Seeger, R., Pople, J.A.: J. Chem. Phys. 72, 650 (1980)

    Article  Google Scholar 

  27. Møller, C., Plesset, M.S.: Phys. Rev. 40, 618 (1934)

    Article  Google Scholar 

  28. Saebo, S., Tong, W., Pulay, P.: J. Chem. Phys. 98, 2170 (1993)

    Article  Google Scholar 

  29. Kaminski, G.A., Maple, J.R., Murphy, R.B., Braden, D.A., Friesner, R.A.: J. Chem. Theory Comput. 1, 248 (2005)

    Article  Google Scholar 

  30. Boys, S.F., Bernardi, R.: Mol. Phys. 19, 553 (1970)

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Dipartimento di Scienze del Farmaco, Università degli Studi G. d’Annunzio, Via Dei Vestini, 31, I-66100, Chieti, Italy

    Cecilia Coletti & Nazzareno Re

Authors
  1. Cecilia Coletti
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nazzareno Re
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Laboratory of Urban and Territorial Systems, University of Basilicata, 10, Viale dell’Ateneo Lucano, 85100, Potenza, Italy

    Beniamino Murgante

  2. Department of Mathematics and Computer Science, University of Perugia, Via Vanvitelli 1, 06123, Perugia, Italy

    Osvaldo Gervasi

  3. Department of Cyber Security Science, Federal University of Technology, Gidan Kwano Campus, Minna, Nigeria

    Sanjay Misra

  4. Faculty of Engineering, Department of Electronics Engineering and Telecommunications, State University of Rio de Janeiro, Rua Sao Francisco Xavier, 524, 50. andar, sala 5145-F, Maracana, 20, 550-013, Rio de Janeiro, RJ, Brazil

    Nadia Nedjah

  5. Department of Production and Systems, University of Minho, Campus de Gualtar, 4710-057, Braga, Portugal

    Ana Maria A. C. Rocha

  6. School of Business Systems, Monash University, 3800, Clayton, VIC, Australia

    David Taniar

  7. Department of Intelligent Informatics, Kyushu Sangyo University, 2-3-1 Matsukadai, Higashi-ku, 813-8503, Fukuoka, Japan

    Bernady O. Apduhan

Rights and permissions

Reprints and permissions

Copyright information

© 2012 Springer-Verlag Berlin Heidelberg

About this paper

Cite this paper

Coletti, C., Re, N. (2012). Performance of DFT and MP2 Approaches for Geometry of Rhenium Allenylidenes Complexes and the Thermodynamics of Phosphines Addition. In: Murgante, B., et al. Computational Science and Its Applications – ICCSA 2012. ICCSA 2012. Lecture Notes in Computer Science, vol 7333. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-31125-3_55

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-31125-3_55

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-31124-6

  • Online ISBN: 978-3-642-31125-3

  • eBook Packages: Computer ScienceComputer Science (R0)

Publish with us

Policies and ethics