Skip to content
Publicly Available Published by De Gruyter July 8, 2011

Defining the hydrogen bond: An account (IUPAC Technical Report)

Elangannan Arunan, Gautam R. Desiraju, Roger A. Klein, Joanna Sadlej, Steve Scheiner, Ibon Alkorta, David C. Clary, Robert H. Crabtree, Joseph J. Dannenberg, Pavel Hobza, Henrik G. Kjaergaard, Anthony C. Legon, Benedetta Mennucci and David J. Nesbitt

The term “hydrogen bond” has been used in the literature for nearly a century now. While its importance has been realized by physicists, chemists, biologists, and material scientists, there has been a continual debate about what this term means. This debate has intensified following some important experimental results, especially in the last decade, which questioned the basis of the traditional view on hydrogen bonding. Most important among them are the direct experimental evidence for a partial covalent nature and the observation of a blue-shift in stretching frequency following XH···Y hydrogen bond formation (XH being the hydrogen bond donor and Y being the hydrogen bond acceptor). Considering the recent experimental and theoretical advances, we have proposed a new definition of the hydrogen bond, which emphasizes the need for evidence. A list of criteria has been provided, and these can be used as evidence for the hydrogen bond formation. This list is followed by some characteristics that are observed in typical hydrogen-bonding environments.

Project Year: 2004, Project Code: 2004-026-2-100


1 The Penguin Dictionary of Science, Penguin, London (1971).Search in Google Scholar

2 L. Pauling. The Nature of the Chemical Bond, Cornell University Press, Ithaca, NY (1960). The first edition was published in 1939.Search in Google Scholar

3 G. C. Pimentel, A. L. McClellan. The Hydrogen Bond, W. H. Freeman, San Francisco (1960).Search in Google Scholar

4 D. Hadzi (Ed.). Hydrogen Bonding, Pergamon, London (1959).Search in Google Scholar

5 W. C. Hamilton, J. A. Ibers. Hydrogen Bonding in Solids, W. A. Benjamin, New York (1968).Search in Google Scholar

6 S. N. Vinogradov, R. H. Linnell. Hydrogen Bonding, Van Nostrand-Reinhold, New York (1971).Search in Google Scholar

7 M. D. Joeston, L. J. Schaad. Hydrogen Bonding, Marcel Dekker, New York (1974).Search in Google Scholar

8 P. Schuster, G. Zundel, C. Sanfordy. The Hydrogen Bond: Recent Developments in Theory and Experiments, Vols. I–III, North Holland, Amsterdam (1976).Search in Google Scholar

9 P. Schuster. Hydrogen Bonds, Springer Verlag, Berlin (1984).10.1007/3-540-12785-2Search in Google Scholar

10 G. A. Jeffrey, W. Saenger. Hydrogen Bonding in Biological Structures, Springer Verlag, Berlin (1991).10.1007/978-3-642-85135-3Search in Google Scholar

11 S. Scheiner. Hydrogen Bonding: A Theoretical Perspective, Oxford University Press, Oxford (1997).Search in Google Scholar

12 G. A. Jeffrey. An Introduction to Hydrogen Bonding, Oxford University Press, Oxford (1997).Search in Google Scholar

13 G. R. Desiraju, T. Steiner. The Weak Hydrogen Bond, Oxford University Press, Oxford (1999).Search in Google Scholar

14 S. J. Grabowski (Ed.). Hydrogen Bonding: New Insights, Springer, Dordrecht (2006).Search in Google Scholar

15 P. Gilli, G. Gilli. The Nature of the Hydrogen Bond, Oxford University Press, Oxford (2009).10.1093/acprof:oso/9780199558964.001.0001Search in Google Scholar

16 10.1021/ja01452a015, W. M. Latimer, W. H. Rodebush. J. Am. Chem. Soc.42, 1419 (1920).Search in Google Scholar

17 10.1002/jlac.19023220302, A. Werner. Leibigs Ann. Chem.322, 261 (1902).Search in Google Scholar

18 P. Pfeiffer. Ann. Chem.398, 137 (1913).10.1002/jlac.19133980203Search in Google Scholar

19 T. S. Moore, T. F. Winmill. J. Chem. Soc.101, 1635 (1912).Search in Google Scholar

20a M. L. Huggins. Phys. Rev.18, 333 (1921);Search in Google Scholar

20b See refs. [2–15] for more historic details and also M. L. Huggins. Angew. Chem., Int. Ed.10, 147 (1971) for a personal account from Huggins.10.1002/anie.197101471Search in Google Scholar

21 10.1080/05704926808050887, A. S. N. Murthy, C. N. R. Rao. Appl. Spectrosc. Rev.2, 69 (1968).Search in Google Scholar

22 10.1021/cr60277a004, P. A. Kollman, L. C. Allen. Chem. Rev.72, 283 (1972).Search in Google Scholar

23 10.1039/cs9800900091, J. Emsley. Chem. Soc. Rev.9, 91 (1980).Search in Google Scholar

24 10.1021/ja00383a012, R. Taylor, O. Kennard. J. Am. Chem. Soc.104, 5063 (1982).Search in Google Scholar

25 10.1021/ar00172a005, M. C. Etter. Acc. Chem. Res.23, 120 (1990).Search in Google Scholar

26 10.1039/cs9952400045, M. A. Suhm, D. J. Nesbitt. Chem. Soc. Rev.24, 45 (1995).Search in Google Scholar

27 10.1039/a827163z, I. Alkorta, I. Roza, J. Ekguero. Chem. Soc. Rev.27, 163 (1998).Search in Google Scholar

28 10.1021/ic9809660, Y. A. Abramov, L. Brammer, W. T. Klooster, R. M. Bullock. Inorg. Chem.37, 6317 (1998).Search in Google Scholar

29 10.1021/jp001507z, T. H. Dunning Jr. J. Phys. Chem. A104, 9062 (2000).Search in Google Scholar

30 10.1021/cr990050q, P. Hobza, Z. Havlas. Chem. Rev.100, 4253 (2000).Search in Google Scholar

31 10.1016/S0166-1280(00)00388-2, C. E. Dykstra, J. M. Lisy. J. Mol. Struct. (Theochem)500, 375 (2000).Search in Google Scholar

32 10.1016/S0022-2860(00)00454-3, G. Gilli, P. Gilli. J. Mol. Struct.552, 1 (2000).Search in Google Scholar

33 10.1021/jp011819h, S. J. Grabowski. J. Phys. Chem. A105, 10739 (2001).Search in Google Scholar

34 10.1021/ja0118542, B. Mennucci. J. Am. Chem. Soc.124, 1506 (2001).Search in Google Scholar

35 10.1016/S0022-2860(02)00220-X, J. J. Dannenberg. J. Mol. Struct.615, 219 (2002).Search in Google Scholar

36 10.1021/ma035322c, J. Yang, S. J. Ding, M. Radosz, Y. Q. Shen. Macromolecules37, 1728 (2004).Search in Google Scholar

37 10.1146/annurev.physchem.48.1.511, C. L. Perrin, J. B. Nielson. Annu. Rev. Phys. Chem.48, 511 (1997).Search in Google Scholar

38 A. V. Iogansen. Spectrochim. Acta, Part A55, 1585 (1999).10.1016/S1386-1425(98)00348-5Search in Google Scholar

39 10.1021/jo070525a, Y. Yang, Z. Y. Yang, Y. P. Yi, J. F. Xiang, C. F. Chen, L. J. Wan, Z. G. Shuai. J. Org. Chem.72, 4936 (2007).Search in Google Scholar PubMed

40 10.1021/jm0498349, E. Carosati, S. Sciabola, G. Cruciani. J. Med. Chem.47, 5114 (2004).Search in Google Scholar PubMed

41 R. McWeeny. Coulson’s Valence, 3rd ed., Oxford University Press, Oxford (1979).Search in Google Scholar

42 J. Israelachvili. Intermolecular and Surface Forces, 2nd ed., Academic Press, New York (1991).Search in Google Scholar

43 A. D. Buckingham. In Intermolecular Interactions from Diatomics to Biopolymers, B. Pullman (Ed.), John Wiley, New York (1978).Search in Google Scholar

44 10.1063/1.1673723, J. Del Bene, J. A. Pople. J. Chem. Phys.52, 4858 (1970).Search in Google Scholar

45 10.1021/ja00082a011, P. Gilli, V. Bertolasi, V. Ferrati, G. Gilli. J. Am. Chem. Soc.116, 909 (1994).Search in Google Scholar

46 F. Weinhold, C. R. Landis. Valency and Bonding, Cambridge University Press, Cambridge (2005).Search in Google Scholar

47 10.1016/j.cplett.2006.11.041, R. A. Klein. Chem. Phys. Lett.433, 165 (2006).Search in Google Scholar

48 10.1021/ja981513x, A. J. Dingley, S. Grzesiek. J. Am. Chem. Soc.120, 8293 (1998).Search in Google Scholar

49 10.1103/PhysRevLett.82.600, E. D. Isaacs, A. Shukla, P. M. Platzman, D. R. Harman, B. Barbiellini, C. A. Tulk. Phys. Rev. Lett.82, 600 (1999).Search in Google Scholar

50 H. Ratajczak, W. J. Orville-Thomas (Eds). Molecular Interactions, p. 15, John Wiley, New York (1980).Search in Google Scholar

51 10.1002/anie.200462704, W. Aquilanti, E. Cornicchi, M. M. Teixidor, N. Saendig, F. Pirani, D. Cappelletti. Angew. Chem., Int. Ed.44, 2356 (2005).Search in Google Scholar PubMed

52 10.1021/jp905584p, L. F. Roncaratti, L. Belpassi, D. Cappelletti, F. Pirani, F. Tarantelli. J. Phys. Chem. A113, 15223 (2009).Search in Google Scholar PubMed

53 10.1021/ja00447a007, H. Umeyama, K. Morokuma. J. Am. Chem. Soc.99, 1316 (1977).Search in Google Scholar

54 10.1021/ja00544a007, J. P. Foster, F. Weinhold. J. Am. Chem. Soc.102, 7211 (1980).Search in Google Scholar

55 10.1063/1.466432, E. D. Glendening, A. Streitwieser. J. Chem. Phys.100, 2900 (1994).Search in Google Scholar

56 10.1021/cr00031a008, B. Jeziorski, R. Moszy?ki, K. Szalewicz. Chem. Rev.94, 1887 (1994).Search in Google Scholar

57 10.1139/v85-334, A. D. Buckingham, P. W. Fowler. Can. J. Chem.63, 2018 (1985).Search in Google Scholar

58 10.1063/1.451441, M. A. Spackman. J. Chem. Phys.85, 6587 (1986).Search in Google Scholar

59 10.1021/ja00198a029, C. E. Dykstra. J. Am. Chem. Soc.111, 6168 (1989).Search in Google Scholar

60 10.1016/S0166-1280(00)00388-2, C. E. Dykstra, J. M. Lisy. THEOCHEM500, 375 (2000).Search in Google Scholar

61 C. M. Hansen. Hansen Solubility Parameters: A User Handbook, CRC Press, Boca Raton (2007).10.1201/9781420006834Search in Google Scholar

62 10.1016/j.eurpolymj.2008.07.005, C. M. Hansen. Eur. Polym. J.44, 2741 (2008).Search in Google Scholar

63 10.1351/goldbook, IUPAC. Compendium of Chemical Terminology, 2nd ed. (the “Gold Book”). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: (2006–) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins.Search in Google Scholar

64 10.1021/ja01307a002, W. D. Kumler. J. Am. Chem. Soc.57, 600 (1935).Search in Google Scholar

65 10.1021/ja01302a059, O. R. Wulf, U. Liddel, S. B. Henricks. J. Am. Chem. Soc.58, 2287 (1936).Search in Google Scholar

66 N. S. Rao, S. K. K. Jakkar. Quart. J. Indian. Inst. Sci.6, 1 (1943).Search in Google Scholar

67 10.1021/jp052460q, E. S. Kryachko, A. Karpfen, F. Remacle. J. Phys. Chem. A109, 7309 (2005).Search in Google Scholar PubMed

68 R. H. Crabtree, P. E. M. Siegbahn, O. Eisenstein, A. L. Reingold, T. Koetzle. Acc. Chem. Res.29, 348 (1996).Search in Google Scholar

69 G. N. Patwari, T. Ibata, N. Mikami. Chem. Phys. Lett.283, 193 (2002).Search in Google Scholar

70 10.1063/1.1597633, H. Cybulski, M. Pecul, J. Sadlej. J. Chem. Phys.119, 5094 (2003).Search in Google Scholar

71 10.1063/1.441747, A. C. Legon, P. D. Soper, W. H. Flygare. J. Chem. Phys.74, 4944 (1981).Search in Google Scholar

72 10.1063/1.2168450, J. M. Merrit, S. Rudic, R. E. Miller. J. Chem. Phys.124, 084301 (2006).Search in Google Scholar PubMed

73 I. Alkorta, J. Rozas, J. Elguero. Ber. Bunsen-Ges. Phys. Chem.102, 429 (1998).Search in Google Scholar

74 10.1016/j.cplett.2006.10.069, S. J. Grabowski, W. A. Sokalski, J. Leszczynski. Chem. Phys. Lett.432, 33 (2006).Search in Google Scholar

75 10.1016/j.cplett.2008.11.009, B. Raghavendra, E. Arunan. Chem. Phys. Lett.467, 37 (2008).Search in Google Scholar

76 10.1351/pac200779061023, F. Fillaux, A. Coussan, M. J. Gutmann. Pure Appl. Chem.79, 1023 (2007).Search in Google Scholar

77 10.1039/cs9932200153, A. C. Legon. Chem. Soc. Rev.22, 153 (1993).Search in Google Scholar

78 M. J. Calhorda. In Hydrogen Bonding: New Insights, S. J. Grabowski (Ed.), pp. 263–292, Springer, Dordrecht (2006).Search in Google Scholar

79 10.1107/S0108768195003673, L. Brammer, D. Zhao, F. T. Ladipo, J. Braddock-Wilking. Acta Crystallogr., Sect. B51, 632 (1995).Search in Google Scholar

80 10.1021/ar800001k, P. Gilli, L. Pretto, V. Bertolasi, G. Gilli. Acc. Chem. Res.42, 33 (2009).Search in Google Scholar PubMed

81 J. Emsley. The Elements, 3rd ed., Oxford University Press, Oxford (1998).Search in Google Scholar

82 10.1063/1.459663, C. M. Lovejoy, D. J. Nesbitt. J. Chem. Phys.93, 5387 (1990).Search in Google Scholar

83 10.1063/1.457178, D. J. Nesbitt, C. M. Lovejoy, T. G. Lindeman, S. V. O’Neil, D. C. Clary. J. Chem. Phys.91, 722 (1989).Search in Google Scholar

84 10.1063/1.1681508, S. J. Harris, S. E. Novick, W. Klemperer. J. Chem. Phys.60, 3208 (1974).Search in Google Scholar

85 10.1016/0009-2614(80)85364-4, E. J. Campbell, M. R. Keenan, L. W. Buxton, T. J. Balle, P. D. Soper, A. C. Legon, W. H. Flygare. Chem. Phys. Lett.70, 420 (1980).Search in Google Scholar

86 10.1063/1.442322, F. A. Baiocchi, T. A. Dixon, C. H. Joyner, W. Klemperer. J. Chem. Phys.75, 2041 (1981).Search in Google Scholar

87 10.1063/1.460379, C. M. Lovejoy, D. J. Nesbitt. J. Chem. Phys.94, 208 (1991).Search in Google Scholar

88 10.1063/1.1540628, S. A. C. McDowell. J. Chem. Phys.118, 4066 (2003).Search in Google Scholar

89 10.1016/j.cplett.2003.11.076, S. Y. Yen, C. H. Mou, H. P. Wu. Chem. Phys. Lett.383, 606 (2004).Search in Google Scholar

90 10.1016/j.cplett.2008.05.019, J. Cukras, J. Sadlej. Chem. Phys. Lett.459, 44 (2008).Search in Google Scholar

91 10.1063/1.433051, S. E. Novick, K. C. Janda, W. Klemperer. J. Chem. Phys.65, 5115 (1976).Search in Google Scholar

92 10.1002/(SICI)1521-3773(19990917)38:18<2686::AID-ANIE2686>3.0.CO;2-6, A. C. Legon. Angew. Chem., Int. Ed.38, 2686 (1999).Search in Google Scholar

93 10.1002/anie.200800128, P. Metrangolo, F. Meyer, T. Pilati, G. Resnati, G. Terraneo. Angew. Chem., Int. Ed.47, 6114 (2008).Search in Google Scholar

94 10.1021/jp062289y, P. Lipkowski, S. J. Grabowski, J. Leszczynski. J. Phys. Chem. A110, 10296 (2006).Search in Google Scholar

95 10.1016/j.theochem.2003.08.004, L. D. Garner-O’Neale, A. F. Bonamy, T. L. Meek, B. G. Patrick. J. Mol. Struct. (Theochem)639, 151 (2003).Search in Google Scholar

96 10.1021/ja020213j, X. Li, L. Liu, H. B. Schlegel. J. Am. Chem. Soc.124, 9639 (2002).Search in Google Scholar PubMed

97 10.1107/S0108768102003890, F. H. Allen. Acta Crystallogr., Sect. B58, 380 (2002); also look at <>.Search in Google Scholar

98 J. Gu, P. E. Bourne (Eds.). The Worldwide Protein Data Bank in Structural Bioinformatics, 2nd ed. pp. 293–303, John Wiley, Hoboken (2009).Search in Google Scholar

99 10.1107/S0365110X6200198X, S. C. Wallwork. Acta Crystallogr.15, 758 (1962) and private communication (2006).Search in Google Scholar

100 10.1039/b411815d, B. Lakshmi, A. G. Samuelson, K. V. Jovan Jose, S. R. Gadre, E. Arunan. New J. Chem.29, 371 (2005).Search in Google Scholar

101 10.1039/b611033a, B. Raghavendra, P. K. Mandal, E. Arunan. Phys. Chem. Chem. Phys.8, 5276 (2006).Search in Google Scholar PubMed

102 10.1021/ja0206947, R. A. Klein. J. Am. Chem. Soc.124, 13931 (2002).Search in Google Scholar PubMed

103 10.1016/j.cplett.2006.04.109, R. A. Klein. Chem. Phys. Lett.425, 128 (2006).Search in Google Scholar

104 10.1021/j100785a001, A. Bondi. J. Phys. Chem.68, 441 (1964).Search in Google Scholar

105 D. R. Lide (Ed.). Handbook of Physics and Chemistry, 90th ed. (Internet version), Sect. 9, CRC Press/Taylor and Francis, Boca Raton (2010).Search in Google Scholar

106 10.1063/1.2191042, N. Elghobashi, L. Gonzalez. J. Chem. Phys.124, 174308 (2006).Search in Google Scholar PubMed

107 10.1016/0009-2614(87)85161-8, A. C. Legon, D. J. Millen, H. M. North. Chem. Phys. Lett.135, 303 (1987).Search in Google Scholar

108 10.1063/1.476470, W. Klopper, M. Quack, M. A. Suhm. J. Chem. Phys.108, 10096 (1998).Search in Google Scholar

109 G. R. Desiraju, S. Steiner. Chem. Commun. 891 (1998).Search in Google Scholar

110 10.1021/j100573a014, B. S. Ault, E. Steinback, G. C. Pimentel. J. Phys. Chem.79, 615 (1975).Search in Google Scholar

111a G. Scoles (Ed.). Atomic and Molecular Beam Methods, Vol. 1, Oxford University Press, New York (1988).Search in Google Scholar

111a G. Scoles (Ed.). Atomic and Molecular Beam Methods, Vol. 2, Oxford University Press, New York (1992).Search in Google Scholar

112 10.1063/1.442316, P. D. Aldrich, A. C. Legon, W. H. Flygare. J. Chem. Phys.75, 2126 (1981).Search in Google Scholar

113 10.1021/ja00415a054, W. G. Read, E. J. Campbell, G. Hendersen, W. H. Flygare. J. Am. Chem. Soc.103, 7670 (1981).Search in Google Scholar

114 10.1063/1.1518999, E. Arunan, T. Emilsson, H. S. Gutowsky, G. T. Fraser, G. de Oliveira, C. E. Dykstra. J. Chem. Phys.117, 9766 (2002).Search in Google Scholar

115 10.1016/j.cplett.2004.06.015, M. Goswami, P. K. Mandal, D. J. Ramdass, E. Arunan. Chem. Phys. Lett.393, 22 (2004).Search in Google Scholar

116 10.1103/PhysRevLett.85.1024, J. S. Loveday, R. J. Nelmes, S. Klotz, J. M. Benson, G. Hamel. Phys. Rev. Lett.85, 1024 (2000).Search in Google Scholar PubMed

117 10.1039/b907708a, M. Goswami, E. Arunan. Phys. Chem. Chem. Phys.11, 8974 (2009).Search in Google Scholar PubMed

118 10.1021/jp060571z, R. Parthasarathi, V. Subramanian, N. Sathyamurthy. J. Phys. Chem. A110, 3349 (2006).Search in Google Scholar PubMed

119 10.1021/ja01295a002, G. E. Hilbert, O. R. Wulf, S. B. Hendricks, U. Liddel. J. Am. Chem. Soc.58, 548 (1936).Search in Google Scholar

120a 10.1063/1.1750085, R. M. Badger, S. H. Bauer. J. Chem. Phys.5, 605 (1937).Search in Google Scholar

120b 10.1063/1.1749952, R. M. Badger, S. H. Bauer. J. Chem. Phys.5, 839 (1937).Search in Google Scholar

121a 10.1021/ja01130a013, L. P. Kuhn. J. Am. Chem. Soc.74, 2492 (1952).Search in Google Scholar

121b 10.1021/ja01646a023, L. P. Kuhn. J. Am. Chem. Soc.76, 4323 (1954).Search in Google Scholar

121c 10.1021/ja01555a016, L. P. Kuhn. J. Am. Chem. Soc.80, 5950 (1958).Search in Google Scholar

122 10.1021/ja055827d, D. L. Howard, P. Jorgensen, H. G. Kjaergaard. J. Am. Chem. Soc.127, 17096 (2005).Search in Google Scholar PubMed

123 10.1021/jp061547o, D. L. Howard, H. G. Kjaergaard. J. Phys. Chem. A110, 9597 (2006).Search in Google Scholar PubMed

124 C. Sandorfy. Top. Curr. Chem.120, 41 (1984).10.1007/3-540-12785-2_2Search in Google Scholar

125 10.1016/j.chemphys.2008.01.028, T. Scharge, D. Luckhaus, M. A. Suhm. Chem. Phys.346, 167 (2008).Search in Google Scholar

126 10.1016/S0009-2614(98)01264-0, P. Hobza, V. Špirko, Z. Havlas, K. Buchhold, B. Reimann, H.-D. Barth, B. Brutschy. Chem. Phys. Lett.299, 180 (1999).Search in Google Scholar

127 10.1021/ja010915t, B. J. van der Veken, W. A. Herrebout, R. Szostak, D. N. Shchepkin, Z. Havlas, P. Hobza. J. Am. Chem. Soc.123, 12290 (2001).Search in Google Scholar PubMed

128 10.1021/ja034656e, I. V. Alabugin, M. Manoharan, S. Peabody, F. Weinhold. J. Am. Chem. Soc.125, 5973 (2003).Search in Google Scholar PubMed

129 10.1021/jp013702z, S. Scheiner, T. Kar. J. Phys. Chem. A106, 1784 (2002).Search in Google Scholar

130 10.1021/ja067545z, J. Joseph, E. D. Jemmis. J. Am. Chem. Soc.129, 4620 (2007).Search in Google Scholar PubMed

131 A. Karpfen, E. S. Kryachko. J. Phys. Chem. A111 (2007).10.1021/jp072717fSearch in Google Scholar PubMed

132 10.1080/08957950701463194, S. K. Sikka. High Pressure Res.27, 313 (2007).Search in Google Scholar

133 10.1063/1.481394, M. Pecul, J. Leszczynski, J. Sadlej. J. Chem. Phys.112, 7930 (2000).Search in Google Scholar

134 10.1039/cs9901900197, A. C. Legon. Chem. Soc. Rev.19, 197 (1990).Search in Google Scholar

135 10.1081/ASR-120030906, E. Arunan, S. Dev, P. K. Mandal. Appl. Spectrosc. Rev.39, 131 (2004).Search in Google Scholar

136 10.1039/c0cp00665c, J. C. López, J. L. Alonso, I. Pe?a, V. Vaquero. Phys. Chem. Chem. Phys.12, 14128 (2010).Search in Google Scholar

137 10.1126/science.271.5251.929, K. Liu, J. D. Cruzan, R. J. Saykally. Science271, 929 (1996).Search in Google Scholar

138 10.1016/S0301-0104(02)00499-8, A. Maris, S. Melandri, W. Caminati, P. G. Favero. Chem. Phys.282, 111 (2002).Search in Google Scholar

139 10.1021/jp9707807, K. Liu, M. G. Brown, R. J. Saykally. J. Phys. Chem. A101, 8995 (1997).Search in Google Scholar

140 10.1063/1.1337051, F. N. Keutsch, M. G. Brown, P. B. Petersen, R. J. Saykally, M. Geleijns, A. van der Avoird. J. Chem. Phys.114, 3994 (2001).Search in Google Scholar

141 10.1021/ar900088g, S. T. Roberts, K. Ramasesha, A. Tokmakoff. Acc. Chem. Res.42, 1239 (2009).Search in Google Scholar PubMed

142 10.1021/jp9009355, H. Biswal, P. R. Shirhatti, S. J. Wategaonkar. J. Phys. Chem. A113, 5633 (2009).Search in Google Scholar PubMed

143 10.1021/jp809121n, S. Maity, G. N. Patwari. J. Phys. Chem. A113, 1760 (2009).Search in Google Scholar PubMed

144 10.1021/jp904233y, V. A. Shubert, C. W. Muller, T. S. Zwier. J. Phys. Chem. A113, 8067 (2009).Search in Google Scholar PubMed

145 10.1039/b915178h, J. Sadlej, J. Cz. Dabrowski, J. E. Rode. Chem. Soc. Rev.39, 1478 (2010).Search in Google Scholar PubMed

146 10.1002/anie.200300611, J. P. Toennies, A. F. Vilesov. Angew. Chem., Int. Ed.43, 2622 (2004).Search in Google Scholar PubMed

147 10.1063/1.3191728, Z. Xue, M. A. Suhm. J. Chem. Phys.131, 054301 (2009).Search in Google Scholar PubMed

148 10.1126/science.1087251, C. J. Fecko, J. D. Eaves, J. J. Loparo, A. Tokmakoff, P. L. Geissler. Science301, 1698 (2003).Search in Google Scholar PubMed

149 10.1063/1.2742385, R. Kumar, J. R. Schmidt, J. L. Skinner. J. Chem. Phys.126, 204107 (2007).Search in Google Scholar PubMed

150 10.1021/cr020694p, E. T. J. Nibbering, T. Elsaesser. Chem. Rev.104, 1887 (2004).Search in Google Scholar PubMed

151 10.1002/anie.200802630, R. Musat, J. P. Renault, M. Candelaresi, D. J. Palmer, S. Le Caer, R. Righini, S. Pommeret. Angew. Chem., Int. Ed.47, 8033 (2008).Search in Google Scholar PubMed

152 10.1007/s10947-009-0010-6, V. P. Voloshin, Y. I. Naberukhin. J. Struct. Chem.50, 78 (2009).Search in Google Scholar

153 10.1021/ja00457a002, P. Kolman. J. Am. Chem. Soc.99, 4875 (1977).Search in Google Scholar

154 10.1007/BF00547998, S. Scheiner. Theor. Chim. Acta57, 71 (1980).Search in Google Scholar

155 10.1063/1.468725, K. A. Peterson, T. H. Dunning. J. Chem. Phys.102, 2032 (1995).Search in Google Scholar

156 10.1146/annurev.pc.45.100194.000323, S. Scheiner. Annu. Rev. Phys. Chem.45, 23 (1994).Search in Google Scholar PubMed

157 10.1021/jp064730q, J. A. Frey, S. Leutwyler. J. Phys. Chem. A110, 12512 (2006).Search in Google Scholar PubMed

158 10.1021/jp046778e, T. P. Tauer, M. E. Derrick, C. D. Sherrill. J. Phys. Chem. A109, 191 (2005).Search in Google Scholar PubMed

159 J. Labanowski, J. Andzelm (Eds). Density Functional Methods in Chemistry, Springer, New York (1991).10.1007/978-1-4612-3136-3Search in Google Scholar

160 10.1021/ar700111a, Y. Zhao, D. G. Truhlar. Acc. Chem. Res.41, 157 (2008).Search in Google Scholar PubMed

161 10.1021/j100179a003, G. Fitzgerald, J. Andzelm. J. Phys. Chem.95, 10531 (1991).Search in Google Scholar

162 10.1063/1.467944, Z. Latajka, Y. Bouteiller. J. Chem. Phys.101, 9793 (1994).Search in Google Scholar

163 10.1063/1.1344891, S. Tsuzuki, H. P. Luthi. J. Chem. Phys.114, 3949 (2001).Search in Google Scholar

164 10.1021/jp0534434, Y. Zhao, O. Tishchenko, D. G. Truhlar. J. Phys. Chem. B109, 19046 (2005).Search in Google Scholar PubMed

165 10.1063/1.1485722, E. M. Cabaleiro-Lago, J. R Otero. J. Chem. Phys.117, 1621 (2002).Search in Google Scholar

166 10.1021/jp810323m, J. S. Arey, P. C. Aeberhard, I.-C. Lin, U. Rothlisberger. J. Phys. Chem. B113, 4726 (2009).Search in Google Scholar

167 10.1021/ct800237n, L. Rao, H. Ke, G. Fu, X. Xu, Y. Yan. J. Chem. Theory Comput.5, 86 (2009).Search in Google Scholar

168 10.1016/0009-2614(94)01027-7, S. Kristyán, P. Pulay. Chem. Phys. Lett.229, 175 (1994).Search in Google Scholar

169 10.1039/b612585a, J. Antony, S. Grimme. Phys. Chem. Chem. Phys.8, 5287 (2006).Search in Google Scholar PubMed

170 10.1002/jcc.20570, P. Jurečka, J. Černý, P. Hobza, D. R. Salahub. J. Comput. Chem.28, 555 (2007).Search in Google Scholar PubMed

171 10.1080/00268977000101561, S. F. Boys, F. Bernardi. Mol. Phys.19, 553 (1970).Search in Google Scholar

172 10.1021/jp9031207, M. M. Deshmukh, S. R. Gadre. J. Phys. Chem. A113, 7927 (2009).Search in Google Scholar PubMed

173 10.1021/jp103470e, K. Wendler, J. Thar, S. Zahn, B. Kirchner. J. Phys. Chem. A114, 9529 (2010).Search in Google Scholar PubMed

174 10.1002/qua.560100211, K. Kitaura, K. Morokuma. Int. J. Quantum Chem.10, 325 (1976).Search in Google Scholar

175 10.1063/1.470171, R. Moszynski, P. E. S. Wormer, B. Jeziorski, A. van der Avoird. J. Chem. Phys.103, 8058 (1995).Search in Google Scholar

176 K. Szalewicz, B. Jeziorski. In: Molecular Interactions. From Van der Waals to Strongly Bound Complexes, S. Scheiner (Ed.), p. 3, John Wiley: New York (1997).Search in Google Scholar

177 10.1063/1.449928, A. E. Reed, F. Weinhold, L. A. Curtiss, D. J. Pochatko. J. Chem. Phys.84, 5687 (1986).Search in Google Scholar

178 10.1021/ja00179a005, K. Wolinski, J. F. Hilton, P. Pulay. J. Am. Chem. Soc.112, 8251 (1990).Search in Google Scholar

179 J. E. D. Bene, S. A. Perera, R. J. Bartlett, M. Yañez, O. Mó, J. Elguero, I. Alkorta. J. Phys. Chem. A107, 107 (2003).Search in Google Scholar

180 10.1063/1.449486, A. E. Reed, L. A. Curtiss, F. Weinhold. J. Chem. Phys.83, 735 (1985).Search in Google Scholar

181 R. F. W. Bader. Atoms in Molecules: A Quantum Theory, Oxford University Press, Oxford (1990).Search in Google Scholar

182 P. Coppens. X-ray Charge Densities and Chemical Bonding, Oxford University Press, Oxford (1997).10.1093/oso/9780195098235.001.0001Search in Google Scholar

183 10.1021/j100024a016, U. Koch, P. L. A. Popelier. J. Phys. Chem.99, 9747 (1995).Search in Google Scholar

184 10.1016/j.molstruc.2004.01.030, P. Kolandaivel, V. Nirmala. J. Mol. Struct.694, 33 (2004).Search in Google Scholar

185 10.1016/S0009-2614(00)00016-6, J. J. Novoa, F. Mota. Chem. Phys. Lett.318, 345 (2000).Search in Google Scholar

186 10.1021/jp046388s, P. Munshi, T. N. Guru Row. J. Phys. Chem. A109, 659 (2005).Search in Google Scholar PubMed

187 10.1021/jp061846d, L. J. Farrugia, C. Evans, M. Tegel. J. Phys. Chem. A110, 7952 (2006).Search in Google Scholar PubMed

188 A. Martin Pendás, E. Fransisco, M. A. Blanco, C. Gatti. Chem.—Eur. J.13, 9632 (2007).Search in Google Scholar

189 10.1021/jp906341r, R. F. W. Bader. J. Phys. Chem. A113, 10391 (2009).Search in Google Scholar PubMed

190 10.1016/j.cplett.2006.08.094, R. A. Klein. Chem. Phys. Lett.429, 633 (2006). For example, this has been observed for the planar and quasi-planar conformational transition states of ethane-1,2-diol, and ethanolamine; unpublished observations, R. A. Klein (2009).Search in Google Scholar

191 10.1021/ja100936w, E. R. Johnson, S. Keinan, P. Mori-Sanchez, J. Contreras-Garcia, A. J. Cohen, W. Yang. J. Am. Chem. Soc.132, 6498 (2010).Search in Google Scholar PubMed PubMed Central

192 E. Arunan, G. R. Desiraju, R. A. Klein, J. Sadlej, S. Scheiner, I. Alkorta, D. C. Clary, R. H. Crabtree, J. J. Dannenberg, P. Hobza, H. G. Kjaergaard, A. C. Legon, B. Mennucci, D. J. Nesbitt. Pure Appl. Chem.83, 1637 (2011).Search in Google Scholar

Online erschienen: 2011-7-8
Erschienen im Druck: 2011-7-8

© 2013 Walter de Gruyter GmbH, Berlin/Boston

Scroll Up Arrow