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.
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Desiraju G R, Steiner T. The Weak Hydrogen Bond. Oxford: Oxford University Press, 1999
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
Tian S X, Yang J. Effects of intramolecular hydrogen bonding on the ionization energies of proline. Angew Chem Int Ed, 2006, 45: 2069–2072
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
Feyereisen M W, Feller D, Dixon D A. Hydrogen bond energy of the water dimer. J Phys Chem, 1996, 100: 2993–2997
Feller D. Application of systematic sequences of wave function to the water dimer. J Chem Phys, 1992, 96: 6104–6114
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
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
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
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
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
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
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
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
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
Leach A R. Molecular modeling principles and applications. London: Addison Wesley Longman, 2001
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
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
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
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
Lehninger A L, Nelson D L, Cox M M. Principles of Biochemistry, 2nd ed. New York: Worth, 1993
Parisien M, Major F. A new catalog of protein β-sheets. Proteins, 2005, 61: 545–558
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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)
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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
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DOI: https://doi.org/10.1007/s11426-009-0017-z