Skip to main content
SpringerLink
Log in

Four-membered ring cyclic ketene –O,O–, –O,S–, –O,N–, –S,S–, –S,N–, and –N,N–acetals and their corresponding cations: a computational study

  • Original Research
  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

A systematic computational study of four-membered cyclic ketene –O,O–, –O,S–, –O,N–, –S,N– and –N,N-acetals as well as their protonated analogs have been performed at the second order Möller Plesset level with a polarized triple zeta basis set. The main purpose of this study was to make predictions about the nucleophilicity of these systems and the variations in nucleophilicity with the hetero atoms. Our calculations suggest that all six target molecules are good nucleophiles, and that the N,N analog is the strongest and the S,S analog the weakest nucleophile. Our results include molecular geometries, bond lengths, proton affinities, vibrational frequencies, and calculated charges.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Ye G, Chen C, Chatterjee S, Collier WE, Zhou A, Song Y, Beard DJ, Pittman CU Jr (2010) Synthesis 1:141

    Article  Google Scholar 

  2. Song Y, Henry WP, De Silva HI, Ye G, Pittman CU Jr (2011) Tetrahedron Lett 52:853

    Article  CAS  Google Scholar 

  3. Ye G, Zhou A, Henry WP, Song Y, Chatterjee S, Beard DJ, Pittman CU Jr (2008) J Org Chem 73:5170

    Article  CAS  Google Scholar 

  4. Chatterjee S, Ye G, Song Y, Barker BL, Pittman CU Jr (2010) Synthesis 19:3384

    Google Scholar 

  5. Chatterjee S, Zhou A, Barker BL, Chen C-L, Song Y, Pittman CU Jr (2010) Synthesis 7:1209

    Google Scholar 

  6. Ye G, Chatterjee S, Li M, Zhou A, Song Y, Barker BL, Chen C-L, Beard DJ, Henry WP, Pittman CU Jr (2010) Tetrahedron 66:2219

    Article  Google Scholar 

  7. Ye G, Henry WP, Chen C-L, Zhou A, Pittman CU Jr (2009) Tetrahedron Lett 50:2135

    Article  CAS  Google Scholar 

  8. Zhou A, Pittman CU Jr (2006) Synthesis 1:37

    Article  Google Scholar 

  9. Chatterjee S, Ye G, Pittman CU Jr (2010) Tetrahedron Lett 51:1139

    Article  CAS  Google Scholar 

  10. Zhou A, Pittman CU Jr (2006) Comb Chem 8(2):262

    Article  CAS  Google Scholar 

  11. Cao L, Wu Z, Pittman CU Jr (1999) J Polym Sci Part A 37:2841

    Article  CAS  Google Scholar 

  12. Cao L, Pittman CU Jr (1999) J Polym Sci Part A 37:2823

    Article  CAS  Google Scholar 

  13. Wu Z, Cao L, Pittman CU Jr (1998) Recent Res Dev Polym Sci 2:467

    CAS  Google Scholar 

  14. Wu Z, Cao L, Pittman CU Jr (1998) J Polym Sci Part A 36:861 (873–881)

    Google Scholar 

  15. Zhu PC, Pittman CU Jr (1996) J Polym Sci Part A 34:169

    Article  CAS  Google Scholar 

  16. Pittman CU Jr, Wu Z, Zhu PC (1997) J Polym Sci Part A 35:485

    Article  Google Scholar 

  17. Zhu PC, Pittman CU Jr (1996) J Polym Sci Part A 34:73

    Article  CAS  Google Scholar 

  18. Liu Y, Pittman CU Jr (1997) J Polym Sci Part A 35:3655

    Article  CAS  Google Scholar 

  19. Liu Y, Keller C, Pittman CU Jr (1997) J Polym Sci Part A 35:3707

    Article  CAS  Google Scholar 

  20. Zhu PC, Liu Y, Lin J, Pittman CU Jr (1996) J Polym Sci Polym Chem Ed 34:2195

    Article  CAS  Google Scholar 

  21. Zhou A, Cao L, Li H, Lu Z, Cho HS, Henry WP, Pittman CU Jr (2006) Tetrahedron 62:4093

    Article  CAS  Google Scholar 

  22. Zhou A, Pittman CU Jr (2005) Tetrahedron Lett 46(22):3801

    Article  CAS  Google Scholar 

  23. McElvain SM (1949) Chem Rev 45:453

    Article  CAS  Google Scholar 

  24. Yokozawa T, Hayashi R, Endo T (1996) Macromolecules 29:3043

    Article  Google Scholar 

  25. Huang Z, Wang M (1993) J Chem Soc Perkin Trans 1:1085

    Article  Google Scholar 

  26. Huang Z, Wang M (1992) J Org Chem 57:184

    Article  CAS  Google Scholar 

  27. Wang Y, Fang D-C, Fu X-Y (1999) Huaxue Wuli Xuebao 12(4):433

    CAS  Google Scholar 

  28. Wang Y, Fang D-C, Fu X-Y (1999) Huaxue Wuli Xuebao 57(8):887

    CAS  Google Scholar 

  29. Bock H, Hirabayashi T, Mohmand S (1982) Chemische Berichte 115(2):492

    Article  CAS  Google Scholar 

  30. Wu P, He S (2000) Huaxue Wuli Xuebao 16(3):243

    Google Scholar 

  31. Thomas HG, Gabriel J, Fleischhauer J, Raabe G (1983) Chemische Berichte 116(1):375

    Article  CAS  Google Scholar 

  32. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785

    Article  CAS  Google Scholar 

  33. Becke AD (1993) J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  34. Frisch MJ, Pople JA (1984) J Chem Phys 80:3265

    Article  CAS  Google Scholar 

  35. Kendall RA, Dunning TH Jr, Harrison RJ (1992) J Chem Phys 96:6769

    Article  Google Scholar 

  36. Beard DJ, Pace CR, Pittman CU Jr, Saebo S (2009) Struct Chem 20:961

    Article  CAS  Google Scholar 

  37. Baker J, Wolinski K, Malagoli M, Kinghorn D, Wolinski P, Magyarfalvi G, Saebo S, Janowski T, Pulay P (2009) J Comput Chem 30:317

    Article  CAS  Google Scholar 

  38. PQS version 3.3, Parallel Quantum Solutions, 2013 Green Acres Road, Fayetteville, AR 72703, USA

  39. Ye G (2008) Ph. D. Dissertation, Mississippi State University

Download references

Acknowledgments

This work has been supported by a grant from the US Department of Education, Title: Creative Research-Based Science Teachers for a Competitive Tomorrow (Grant # P381A080011 09010025).

Author information

Authors and Affiliations

  1. Department of Chemistry, Mississippi State University, P.O. Box 9573, Mississippi State, MS, 39762, USA

    Debbie J. Beard, Sumer A. Barakat, Nathanael B. Lockhart, Chandler R. Pace, Charles U. Pittman Jr. & Svein Saebo

  2. Department of Curriculum and Instruction, Mississippi State University, P.O. Box 9703, Mississippi State, MS, 39762, USA

    Burnette W. Hamil

Authors
  1. Debbie J. Beard
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sumer A. Barakat
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nathanael B. Lockhart
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Chandler R. Pace
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Charles U. Pittman Jr.
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Burnette W. Hamil
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Svein Saebo
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Svein Saebo.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 143 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Beard, D.J., Barakat, S.A., Lockhart, N.B. et al. Four-membered ring cyclic ketene –O,O–, –O,S–, –O,N–, –S,S–, –S,N–, and –N,N–acetals and their corresponding cations: a computational study. Struct Chem 23, 351–357 (2012). https://doi.org/10.1007/s11224-011-9869-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-011-9869-x

Keywords

Search

Navigation