Skip to main content
Log in

A new method for quick predicting the strength of intermolecular hydrogen bonds

Science in China Series B: Chemistry Aims and scope Submit manuscript

Abstract

A new method is proposed to quick predict the strength of intermolecular hydrogen bonds. The method is employed to produce the hydrogen-bonding potential energy curves of twenty-nine hydrogen-bonded dimers. The calculation results show that the hydrogen-bonding potential energy curves obtained from this method are in good agreement with those obtained from MP2/6-31+G** calculations by including the BSSE correction, which demonstrate that the method proposed in this work can be used to calculate the hydrogen-bonding interactions in peptides.

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

Access this article

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Desiraju G R, Steiner T. The Weak Hydrogen Bond. Oxford: Oxford University Press, 1999

    Google Scholar 

  2. Dong H, Hua W, Li S. Estimation on the individual hydrogen bond strength in molecules with multiple hydrogen bonds. J Phys Chem, 2007, 111(15): 2941–2945

    Article  CAS  Google Scholar 

  3. Tian S X, Yang J. Effects of intramolecular hydrogen bonding on the ionization energies of proline. Angew Chem Int Ed, 2006, 45: 2069–2072

    Article  CAS  Google Scholar 

  4. Chen Y F, Dannenberg J J. Cooperative 4-pyridone H-bonds with extraordinary stability. A DFT molecular orbital study. J Am Chem Soc, 2006, 128: 8100–8101

    Article  CAS  Google Scholar 

  5. Feyereisen M W, Feller D, Dixon D A. Hydrogen bond energy of the water dimer. J Phys Chem, 1996, 100: 2993–2997

    Article  CAS  Google Scholar 

  6. Feller D. Application of systematic sequences of wave function to the water dimer. J Chem Phys, 1992, 96: 6104–6114

    Article  CAS  Google Scholar 

  7. Vargas R, Garza J, Friesner R A, Stern H, Hay B P, Dixon D A. Strength of the N—H⋯O=C and C—H⋯=C bonds in formamide and N-methylacetamide dimers. J Phys Chem A, 2001, 105:4963–4968

    Article  CAS  Google Scholar 

  8. Kim K, Jordan K D. Comparison of density function and MP2 calculations on the water monomer and dimer. J Phys Chem, 1994, 98: 10089–10094

    Article  CAS  Google Scholar 

  9. Wang C S, Wang J, Yang, Z Z. A new method for quick determining conformation stability of Alanine-α-polypeptide (in Chinese). Chem J Chin Uni, 2005, 26(3): 485–488

    CAS  Google Scholar 

  10. Wang C S, Wang X W, Wang J, Yang, Z Z. Special hydrogen method for predicting conformation stability of Alanine-α-tetrapeptide (in Chinese). Acta Chim Sin, 2006, 64(2): 104–110

    CAS  Google Scholar 

  11. Wang C S, Zhang Y, Gao K, Yang, Z Z. A new scheme for determining the intramolecular seven-membered ring N—H⋯O=C hydrogenbonding energies of glycine and alanine peptides. J Chem Phys, 2005, 123: 024307-1-024307-8

  12. Scheiner S. Contributions of NH⋯O and CH⋯O hydrogen bonds to stability of β-sheets in proteins. J Phys Chem B, 2006, 110: 18670–18679

    Article  CAS  Google Scholar 

  13. Chin W, Piuzzi F, Dimicoli I, Mons M. Probing the competition between secondary structures and local preferences in gas phase isolated peptide backbones. Phys Chem Chem Phys, 2006, 8: 1033–1048

    Article  CAS  Google Scholar 

  14. Kim K, Jordan K D. Comparison of density function and MP2 calculations on the water monomer and dimer. J Phys Chem, 1994, 98: 10089–10094

    Article  CAS  Google Scholar 

  15. Ireta J, Neugebauer J, Scheffler M. On the accuracy of DFT for describing hydrogen bonds: dependence on the bond directionality. J Phys Chem A, 2004, 108: 5692–5698

    Article  CAS  Google Scholar 

  16. Leach A R. Molecular modeling principles and applications. London: Addison Wesley Longman, 2001

    Google Scholar 

  17. Boys S F, Bernardi F. Calculations of small molecular interactions by differences of separate total energies. Some procedures with reduced errors. Mol Phys, 1970, 19: 553–556

    Article  CAS  Google Scholar 

  18. Simon S, Duran M, Dannenberg J J. How does basis set superposition error change the potential surfaces for hydrogen-bonded dimers? J Chem Phys, 1996, 105: 11024–11031

    Article  CAS  Google Scholar 

  19. Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Zakrzewski V G, Montgomery J AJr., Stratmann R E, Burant J C, Dapprich S, Millam J M, Daniels A D, Kudin K N, Strain M C, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson G A, Ayala P Y, Cui Q, Morokuma K, Malick D K, Rabuck A D, Raghavachari K, Foresman J B, Cioslowski J, Ortiz J V, Baboul A D, Stefanov B B, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin R L, Fox D J, Keith T, Al-Laham M A, Peng C Y, Nanayakkara A, Gonzalez C, Challacombe M, Gill P M W, Johnson B, Chem W, Wong M W, Andres J L, Gonzalez C, Head-Gordon M, Replogle E S, Pople J A. Gaussian 03; Pittsburgh: Gaussian Inc., 2003

  20. Cornell W D, Spellmeyer C, Fox T, Caldwell J W, Kollman P A. A second generation force field for the simulation of proteins, nucleic acids, and organic molecular. J Am Chem Soc, 1995, 117: 5179–5197

    Article  CAS  Google Scholar 

  21. Lehninger A L, Nelson D L, Cox M M. Principles of Biochemistry, 2nd ed. New York: Worth, 1993

    Google Scholar 

  22. Parisien M, Major F. A new catalog of protein β-sheets. Proteins, 2005, 61: 545–558

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to ChangSheng Wang.

Additional information

Supported by the National Natural Science Foundation of China (Grants Nos. 20573049 and 20633050) and the research fund of the Educational Department of Liaoning Province (2004C019, 20060469)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sun, C., Zhang, Y., Jiang, X. et al. A new method for quick predicting the strength of intermolecular hydrogen bonds. Sci. China Ser. B-Chem. 52, 153–160 (2009). https://doi.org/10.1007/s11426-009-0017-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-009-0017-z

Keywords

Navigation