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 X–H···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
References
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).10.1007/978-1-4020-4853-1Search 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).10.1039/CT9120101635Search 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).10.1021/ar950150sSearch in Google Scholar
69 G. N. Patwari, T. Ibata, N. Mikami. Chem. Phys. Lett.283, 193 (2002).10.1016/S0301-0104(02)00529-3Search 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).10.1002/bbpc.19981020323Search 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 <http://www.ccdc.cam.ac.uk/>.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).10.1002/chem.200700408Search 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).10.1351/PAC-REC-10-01-02Search in Google Scholar
© 2013 Walter de Gruyter GmbH, Berlin/Boston