Skip to main content
SpringerLink
Log in

Comparative study of NH···O and NH···S intramolecular hydrogen bonds in β-aminoacrolein, β-thioaminoacrolein and their halogenated derivatives by some usual methods

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

Abstract

We first use the second-order Møller–Plesset theory to optimize β-aminoacrolein, β-thioaminoacrolein and a set of their halogenated derivatives, which involve N–H···O and N–H···S hydrogen bonds. Then, four different methods, namely rotation barrier method (RBM), isodesmic reaction method (IRM), geometry corrected method (GCM) and related rotamers method, (RRM) are utilized to estimate the intramolecular hydrogen bond (IMHB) energies. The linear correlations between the estimated IMHB energies and some hydrogen bond strength descriptors such as geometrical, electron density topological and spectroscopic parameters are obtained. According to our data, RRM and RBM have the best linear correlations with all of the hydrogen bond descriptors, while GCM and IRM do not reveal suitable results. It is assumed that the performance or reliability of the estimating methods is determined based on the value of squared regression coefficients (R 2). By adding the results of the previous studies including OH···O, OH···S and NH···O hydrogen bond units to the present obtained data, the methods can be sorted according to their relative reliability as follows: RRM > RBM ≫ GCM > IRM.

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

Scheme 1
Scheme 2
Scheme 3
Scheme 4

Similar content being viewed by others

References

  1. Jeffrey GA (1997) An introduction to hydrogen bonding. Oxford University Press, New York

    Google Scholar 

  2. Grabowski SJ (2006) Hydrogen bonding-newinsights. Springer, Berlin

    Book  Google Scholar 

  3. Scheiner S (1997) Hydrogen bonding; a theoretical perspective. University Press, New York

    Google Scholar 

  4. Gilli G, Gilli P (2009) The nature of hydrogen bond. Oxford University Press, New York

    Book  Google Scholar 

  5. Sanz P, Mό O, Yáñez M, Elguero J (2007) Chem Phys Chem 8:1950

    Article  CAS  Google Scholar 

  6. Sanz P, Mό O, Yáñez M, Elguero J (2008) Chem-Eur J 14:4225

    Article  CAS  Google Scholar 

  7. Alkorta I, Elguero J, Mό O, Yáñez M, Bene JD (2004) Mol Phys 102:2563

    Article  CAS  Google Scholar 

  8. Alkorta I, Elguero J, Mό O, Yáñez M, Bene JD (2005) Chem Phys Lett 411:411

    Article  CAS  Google Scholar 

  9. Emsley J (1984) Structure and bonding, vol 2. Springer, Berlin

    Google Scholar 

  10. Woodford JN (2007) J Phys Chem 111A:8519

    Article  Google Scholar 

  11. Nowroozi A, Raissi H (2006) J Mol Struct (THEOCHEM) 759:93

    Article  CAS  Google Scholar 

  12. Raissi H, Nowroozi A, Roozbeh M, Farzad F (2006) J Mol Struct 787:148

    Article  CAS  Google Scholar 

  13. Nowroozi A, Roohi H, Sadeghi MS, Sheibaninia M (2011) Int J Quantum Chem 111:578

    Article  CAS  Google Scholar 

  14. Kuldova K, Corval A, Trommsdorff HP, Lehn JM (1997) J Phys Chem 101A:6850

    Article  Google Scholar 

  15. Douhal A, Sastre R (1994) Chem Phys Lett 219:91

    Article  CAS  Google Scholar 

  16. Sytnic A, Del Valle JC (1995) J Phys Chem 99:13028

    Article  Google Scholar 

  17. Schuster P, Zundel G (1976) The hydrogen bond. Recent Developmentin Theory and Experiment, Nourth-Holland

    Google Scholar 

  18. Buemi G, Zuccarello F (2004) Chem Phys 306:115

    Article  CAS  Google Scholar 

  19. Jablonski M, Kaczmarek A, Sadlej AJ (2006) J Phys Chem A 110:10890

    Article  CAS  Google Scholar 

  20. Nowroozi A, Raissi H, Farzad F (2005) J Mol Struct (THEOCHEM) 730:161

    Article  CAS  Google Scholar 

  21. Rozas I, Alkorta I, Elguero J (2001) J Phys Chem A 105:10462

    Article  CAS  Google Scholar 

  22. Nowroozi A, Raissi H, Hajiabadi H, Mohammadzadeh P (2011) Int J Quantum Chem 111:3040

    Article  CAS  Google Scholar 

  23. Nowroozi A, Hajiabadi H, Akbari F (2014) Struct Chem 25:251

    Article  CAS  Google Scholar 

  24. Nowroozi A, Roohi H, Hajiabadi H, Raissi H, Khalilinia E, Najafi B (2011) Comput Theo Chem 963:517

    Article  CAS  Google Scholar 

  25. Hajiabadi H, Nowroozi A, Hasani H, Mohammadzadeh P, Raissi H (2012) Int J Quantum Chem 112:1384

    Article  CAS  Google Scholar 

  26. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zarzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (2003) Gaussian 03 (Revision B.01). Gaussian, Inc., Pittsburgh, PA

  27. Biegler-König F, Schönbohm J, Bayles D (2001) AIM 2000: a program to analyze and visualize atoms in molecules. J Comp Chem 22:545

    Article  Google Scholar 

  28. Glendening DE, Reed AE, Carpenter JE, Weinhold F NBO Version3.1

  29. Jablonski M (2010) Chem Phys 376:76

    Article  CAS  Google Scholar 

  30. Grabowski SJ (2004) J Phys Org Chem 17:18

    Article  CAS  Google Scholar 

  31. Jablonski M (2012) J Phys Chem A 116:3753

    Article  CAS  Google Scholar 

  32. Buemi G, Zuccarello F (2002) J Mol Struct (THEOCHEM) 581:71

    Article  CAS  Google Scholar 

  33. Musin RN, Mariam YH (2006) J Phys Org Chem 19:425

    Article  CAS  Google Scholar 

  34. Koch W, Frenking G, Gauss J, Cremer D, Collins JR (1987) J Am Chem Soc 109:5917

    Article  CAS  Google Scholar 

  35. Rozas I, Alkorta I, Elguero J (2000) J Am Chem Soc 122:11154

    Article  CAS  Google Scholar 

  36. Espinosa E, Molins M, Lecomte C (1998) Chem Phys Lett 285:170

    Article  CAS  Google Scholar 

  37. Bader RFW (1990) Atoms in molecules. A Quantum Theory; Clarendon, Oxford

    Google Scholar 

  38. Grabowski SJ (2001) J Mol Struct 562:137

    Article  CAS  Google Scholar 

  39. Grabowski SJ (1999) Chem Phys Lett 312:542

    Article  CAS  Google Scholar 

  40. Espinosa E, Molins M (2000) Chem Phys 113:5686

    CAS  Google Scholar 

  41. Grabowski SJ (2001) Chem Phys Lett 338:361

    Article  CAS  Google Scholar 

  42. Reed AE, Curtis LA, Weinhold FA (1988) Chem Rev 88:899–926

    Article  CAS  Google Scholar 

  43. Raissi H, Farzad F, Nowroozi A (2005) J Mol Struct 752:130

    Article  CAS  Google Scholar 

  44. Raissi H, Nowroozi A, Farzad F (2006) Spectrochim. Acta. A 63:729

    Article  Google Scholar 

  45. Raissi H, Nowroozi A, Hakimi M (2006) Spectrochim Acta A 65:605

    Article  Google Scholar 

  46. Pratt DA, Heer MI, Mulder P, Ingold KU (2001) J Am Chem Soc 123:5518

    Article  CAS  Google Scholar 

  47. Song KS, Liu L, Guo QX (2003) J Org Chem 68:262

    Article  CAS  Google Scholar 

  48. Borges DS, Martinho SJA (1998) J Phys Chem Ref Data 1998(27):707

    Article  Google Scholar 

  49. Deshmukh MM, Suresh CH, Gadre SR (2007) J Phys Chem A 111:6472

    Article  CAS  Google Scholar 

  50. Jabłonski M, Monaco G (2013) J Chem Inf Model 53:1661

    Article  Google Scholar 

  51. Nowroozi A, Mohammadzadeh Jahani P, Asli N, Hajiabadi H, Dahmardeh S, Raissi H (2012) Int J Quant Chem 112:489

    Article  CAS  Google Scholar 

  52. Mohammadzadeh Jahani P, Nowroozi A, Hajiabadi H, Hassani H (2012) Struct Chem 23:1941

    Article  CAS  Google Scholar 

  53. Mohammadzadeh Jahani P, Nowroozi A (2013) Int J Quantum Chem 113:102

    Article  Google Scholar 

Download references

Acknowledgments

The authors thank the University of Sistan and Baluchestan (USB) for the financial supports.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan (USB), P.O. Box 98135-674, Zahedan, Iran

    Alireza Nowroozi & Ehsan Masumian

Authors
  1. Alireza Nowroozi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ehsan Masumian
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Alireza Nowroozi.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nowroozi, A., Masumian, E. Comparative study of NH···O and NH···S intramolecular hydrogen bonds in β-aminoacrolein, β-thioaminoacrolein and their halogenated derivatives by some usual methods. Struct Chem 28, 587–596 (2017). https://doi.org/10.1007/s11224-016-0823-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-016-0823-9

Keywords

Search

Navigation