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RESEARCH FRONT
Contents Vol 63(12)

Directional Weak Intermolecular Interactions: σ-Hole Bonding

Jane S. Murray A , Kevin E. Riley B , Peter Politzer A and Timothy Clark C D
+ Author Affiliations
- Author Affiliations

A CleveTheoComp LLC, 1951 W. 26th Street, Suite 409, Cleveland, OH 44126, USA.

B Department of Chemistry, PO Box 23346, University of Puerto Rico, Rio Piedras, PR 00931, Puerto Rico.

C Computer-Chemie-Centrum and Interdisciplinary Center for Molecular Materials, Friedrich-Alexander-Universität, Erlangen-Nürnberg, Nägelsbachstrasse 25, 91052 Erlangen, Germany.

D Centre for Molecular Design, University of Portsmouth, Mercantile House, Portsmouth, PO1 2EG, UK.

E Corresponding author. Email: tim.clark@chemie.uni-erlangen.de

Australian Journal of Chemistry 63(12) 1598-1607 https://doi.org/10.1071/CH10259
Submitted: 7 July 2010  Accepted: 3 October 2010   Published: 6 December 2010

Abstract

The prototypical directional weak interactions, hydrogen bonding and σ-hole bonding (including the special case of halogen bonding) are reviewed in a united picture that depends on the anisotropic nature of the molecular electrostatic potential around the donor atom. Qualitative descriptions of the effects that lead to these anisotropic distributions are given and examples of the importance of σ-hole bonding in crystal engineering and biological systems are discussed.


References

[1]  R. E. Rosenfield, Jr, R. Parthasarathy, J. D. Dunitz, J. Am. Chem. Soc. 1977, 99, 4860.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  T. N. Guru Row, R. Parthasarathy, J. Am. Chem. Soc. 1981, 103, 477.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  P. Murray-Rust, W. D. S. Motherwell, J. Am. Chem. Soc. 1979, 101, 4374.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  P. Murray-Rust, W. C. Stallings, C. T. Monti, R. K. Preston, J. P. Glusker, J. Am. Chem. Soc. 1983, 105, 3206.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  N. Ramasubbu, R. Parthasarathy, P. Murray-Rust, J. Am. Chem. Soc. 1986, 108, 4308.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  R. F. Stewart, Chem. Phys. Lett. 1979, 65, 335.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  Chemical Applications of Atomic and Molecular Electrostatic Potentials 1981 (Eds P. Politzer, D. G. Truhlar) (Plenum Press: New York, NY).

[8]  J. Meister, W. H. E. Schwarz, J. Phys. Chem. 1994, 98, 8245.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  K. B. Wiberg, P. R. Rablen, J. Comput. Chem. 1993, 14, 1504.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  J. S. Murray, P. Politzer, J. Mol. Struct. Theochem. 1998, 425, 107.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  P. Politzer, J. S. Murray, M. C. Concha, Int. J. Quantum Chem. 2002, 88, 19.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  R. F. W. Bader, M. T. Carroll, J. R. Cheeseman, C. Chang, J. Am. Chem. Soc. 1987, 109, 7968.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  J. S. Murray, P. Politzer, Croat. Chem. Acta 2009, 82, 267.

[14]  F. A. Bulat, A. Toro-Labbé, T. Brinck, J. S. Murray, P. Politzer, J. Mol. Model. 2010, 16, 1679.
         | Crossref | GoogleScholarGoogle Scholar | 20361346PubMed |

[15]  T. Clark, M. Hennemann, J. S. Murray, P. Politzer, J. Mol. Model. 2007, 13, 291.
         | Crossref | GoogleScholarGoogle Scholar | 16927107PubMed |

[16]  P. Politzer, J. S. Murray, T. Clark, Phys. Chem. Chem. Phys. 2010, 12, 7748.
         | Crossref | GoogleScholarGoogle Scholar | 20571692PubMed |

[17]  J. S. Murray, P. Lane, P. Politzer, J. Mol. Model. 2009, 15, 723.
         | Crossref | GoogleScholarGoogle Scholar | 19082643PubMed |

[18]  J. S. Murray, P. Lane, P. Politzer, Int. J. Quantum Chem. 2007, 107, 2286.
         | Crossref | GoogleScholarGoogle Scholar |

[19]  P. Politzer, J. S. Murray, M. C. Concha, J. Mol. Model. 2007, 13, 643.
         | Crossref | GoogleScholarGoogle Scholar | 17361403PubMed |

[20]  J. S. Murray, P. Lane, T. Clark, P. Politzer, J. Mol. Model. 2007, 13, 1033.
         | Crossref | GoogleScholarGoogle Scholar | 17647029PubMed |

[21]  T. Di Paolo, C. Sandorfy, Chem. Phys. Lett. 1974, 26, 466.
         | Crossref | GoogleScholarGoogle Scholar |

[22]  T. Di Paolo, C. Sandorfy, Can. J. Chem. 1974, 52, 3612.
         | Crossref | GoogleScholarGoogle Scholar |

[23]  E. Corradi, S. V. Meille, M. T. Messina, P. Metrangolo, G. Resnati, Angew. Chem. Int. Ed. 2000, 39, 1782.
         | Crossref | GoogleScholarGoogle Scholar |

[24]  P. Politzer, J. S. Murray, P. Lane, Int. J. Quantum Chem. 2007, 107, 3046.
         | Crossref | GoogleScholarGoogle Scholar |

[25]  I. Alkorta, F. Blanco, M. Solimannejad, J. Elguero, J. Phys. Chem. A 2008, 112, 10856.
         | Crossref | GoogleScholarGoogle Scholar | 18837495PubMed |

[26]  K. E. Riley, J. S. Murray, M. C. Concha, P. Hobza, P. Politzer, J. Chem. Theory Comput. 2009, 5, 155.
         | Crossref | GoogleScholarGoogle Scholar |

[27]  P. Politzer, P. Lane, M. C. Concha, Y. Ma, J. S. Murray, J. Mol. Model. 2007, 13, 305.
         | Crossref | GoogleScholarGoogle Scholar | 17013631PubMed |

[28]  P. Politzer, J. S. Murray, M. C. Concha, J. Mol. Model. 2008, 14, 659.
         | Crossref | GoogleScholarGoogle Scholar | 18317819PubMed |

[29]  F.-F. Wang, J.-H. Hou, Z.-R. Li, D. Wu, Y. Li, Z.-Y. Lu, W.-L. Cao, J. Chem. Phys. 2007, 126, 144301.
         | Crossref | GoogleScholarGoogle Scholar | 17444706PubMed |

[30]  P. Auffinger, F. A. Hays, E. Westhof, P. Shing Ho, Proc. Natl. Acad. Sci. USA 2004, 101, 16789.
         | Crossref | GoogleScholarGoogle Scholar |

[31]  H. Hagelin, J. S. Murray, T. Brinck, M. Berthelot, P. Politzer, Can. J. Chem. 1995, 73, 483.
         | Crossref | GoogleScholarGoogle Scholar |

[32]  Z. Shields, J. S. Murray, P. Politzer, Int. J. Quantum Chem. 2010, 110, 2823.
         | Crossref | GoogleScholarGoogle Scholar |

[33]  K. E. Riley, P. Hobza, J. Chem. Theory Comput. 2008, 4, 232.
         | Crossref | GoogleScholarGoogle Scholar |

[34]  M. Palusiak, J. Mol. Struct. Theochem. 2010, 945, 89.
         | Crossref | GoogleScholarGoogle Scholar |

[35]  W. Wang, N.-B. Wong, W. Zheng, A. Tian, J. Phys. Chem. A 2004, 108, 1799.
         | Crossref | GoogleScholarGoogle Scholar |

[36]  J. S. Murray, M. C. Concha, P. Lane, P. Hobza, P. Politzer, J. Mol. Model. 2008, 14, 699.
         | Crossref | GoogleScholarGoogle Scholar | 18438691PubMed |

[37]  K. Hermansson, J. Phys. Chem. A 2002, 106, 4695.
         | Crossref | GoogleScholarGoogle Scholar |

[38]  W. A. Sokalski, S. M. Roszak, J. Mol. Struct. Theochem. 1991, 234, 387.
         | Crossref | GoogleScholarGoogle Scholar |

[39]  R. Z. Khaliullin, A. T. Bell, M. Head-Gordon, Chemistry 2009, 15, 851.
         | Crossref | GoogleScholarGoogle Scholar | 19086050PubMed |

[40]  K. D. Sen, P. Politzer, J. Chem. Phys. 1989, 90, 4370.
         | Crossref | GoogleScholarGoogle Scholar |

[41]  W. Kutzelnigg, Angew. Chem. Int. Ed. Engl. 1984, 23, 272.
         | Crossref | GoogleScholarGoogle Scholar |

[42]  E. D. Stevens, Mol. Phys. 1979, 37, 27.
         | Crossref | GoogleScholarGoogle Scholar |

[43]  S. C. Nyburg, W. Wong-Ng, Proc. R. Soc. Lond. A Math. Phys. Sci. 1979, 367, 29.
         | Crossref | GoogleScholarGoogle Scholar |

[44]  S. Ikuta, J. Mol. Struct. Theochem. 1990, 205, 191.
         | Crossref | GoogleScholarGoogle Scholar |

[45]  S. L. Price, A. J. Stone, J. Lucas, R. S. Rowland, A. E. Thornley, J. Am. Chem. Soc. 1994, 116, 4910.
         | Crossref | GoogleScholarGoogle Scholar |

[46]  V. G. Tsirelson, P. F. Zou, T.-H. Tang, R. F. W. Bader, Acta Crystallogr. 1995, A51, 143.

[47]  J. P. M. Lommerse, A. J. Stone, R. Taylor, F. H. Allen, J. Am. Chem. Soc. 1996, 118, 3108.
         | Crossref | GoogleScholarGoogle Scholar |

[48]  E. Bilewicz, A. J. Rybarczyk-Pirek, A. T. Dubis, S. J. Grabowski, J.Mol. Struct. 2007, 829, 208.
         | Crossref | GoogleScholarGoogle Scholar |

[49]  S. C. Nyburg, Acta Cryst. 1979, A35, 641.
         | Crossref | GoogleScholarGoogle Scholar |

[50]  J. P. Perdew, Electronic Structure of Solids ’91 1991, p. 11 (Eds P. Ziesche, H. Eschrig) (Akademie Verlag: Berlin).
      J. P. Perdew, J. A. Chevary, S. H. Vosko, K. A. Jackson, M. R. Pederson, D. J. Singh, C. Fiolhais, Phys. Rev. B 1992, 46, 6671. (Erratum: Phys. Rev. B 1993, 48, 4978. 10.1103/PHYSREVB.46.6671
      (c) J. P. Perdew, K. Burke, Y. Wang, Phys. Rev. B 1996, 54, 16533.
         | Crossref | GoogleScholarGoogle Scholar |
      K. Burke, J. P. Perdew, Y. Wang, in Electronic Density Functional Theory: Recent Progress and New Directions 1998 (Eds J. F. Dobson, G. Vignale, M. P. Das) (Springer: Heidelberg).

[51]  B. Delley, Modern Density Functional Theory: a Tool for Chemistry. Theoretical and Computational Chemistry, Vol. 2 1995 (Eds J. M. Seminario, P. Politzer) (Elsevier Science: Amsterdam).

[52]  O. Ermer, S. Lifson, J. Am. Chem. Soc. 1973, 95, 4121.
         | Crossref | GoogleScholarGoogle Scholar |

[53]  U. Burkert, N. L. Allinger, Molecular Mechanics. ACS Monograph 177 1982 (American Chemical Society: Washington, DC).

[54]  A. C. Legon, Angew. Chem. Int. Ed. 1999, 38, 2686.
         | Crossref | GoogleScholarGoogle Scholar |

[55]  A. C. Legon, Phys. Chem. Chem. Phys. 2010, 12, 7736.
         | Crossref | GoogleScholarGoogle Scholar | 20495729PubMed |

[56]  C. Guardigli, R. Liantonio, M. L. Mele, P. Metrangolo, G. Resnati, T. Pilati, Supramol. Chem. 2003, 15, 177.
         | Crossref | GoogleScholarGoogle Scholar |

[57]  T. Caronna, R. Liantonio, T. A. Logothetis, P. Metrangolo, T. Pilati, G. Resnati, J. Am. Chem. Soc. 2004, 126, 4500.
         | Crossref | GoogleScholarGoogle Scholar | 15070351PubMed |

[58]  P. Metrangolo, H. Neukirch, T. Pilati, G. Resnati, Acc. Chem. Res. 2005, 38, 386.
         | Crossref | GoogleScholarGoogle Scholar | 15895976PubMed |

[59]  P. Metrangolo, G. Resnati, T. Pilati, R. Liantonio, F. Meyer, J. Polym. Sci. A 2007, 45, 1.
         | Crossref | GoogleScholarGoogle Scholar |

[60]  P. Metrangolo, G. Resnati, T. Pilati, S. Biella, Halogen Bonding: Fundamentals and Applications 2008, pp. 105–136 (Eds P. Metrangolo, G. Resnati) (Springer: Berlin).

[61]  Q. Chu, Z. Wang, Q. Huang, C. Yan, S. Zhu, J. Am. Chem. Soc. 2001, 123, 11069.
         | Crossref | GoogleScholarGoogle Scholar | 11686715PubMed |

[62]  R. Boese, M. T. Kirchner, W. E. Billups, L. R. Norman, Angew. Chem. Int. Ed. 2003, 42, 1961.
         | Crossref | GoogleScholarGoogle Scholar |

[63]  A. F. Cozzolino, I. Vargas-Baca, S. Mansour, A. H. Mahmoudkhani, J. Am. Chem. Soc. 2005, 127, 3184.
         | Crossref | GoogleScholarGoogle Scholar | 15740158PubMed |

[64]  D. Cinčić, T. Friščić, W. Jones, J. Am. Chem. Soc. 2008, 130, 7524.
         | Crossref | GoogleScholarGoogle Scholar | 18491900PubMed |

[65]  K. Rissanen, CrystEngComm 2008, 10, 1107.
         | Crossref | GoogleScholarGoogle Scholar |

[66]  C. V. Ramana, S. Chatterjee, K. A. Durngkar, R. G. Gonnade, CrystEngComm 2009, 11, 143.
         | Crossref | GoogleScholarGoogle Scholar |

[67]  A. Forni, J. Phys. Chem. A 2009, 113, 3403.
         | Crossref | GoogleScholarGoogle Scholar | 19281207PubMed |

[68]  G. M. Espallargas, F. Zordan, L. A. Marín, H. Adams, K. Shankland, J. van de Streek, L. Brammer, Chemistry 2009, 15, 7554.
         | Crossref | GoogleScholarGoogle Scholar | 19593826PubMed |

[69]  Y. Lu, Y. Wang, W. Zhu, Phys. Chem. Chem. Phys. 2010, 12, 4543.
         | Crossref | GoogleScholarGoogle Scholar | 20428531PubMed |

[70]  H. Matter, M. Nazaré, S. Güssregen, D. W. Will, H. Schreuder, A. Bauer, M. Urmann, K. Ritter, M. Wagner, V. Wehner, Angew. Chem. Int. Ed. 2009, 48, 2911.
         | Crossref | GoogleScholarGoogle Scholar |

[71]  L. Liu, W. A. Basse, B. W. Matthews, J. Mol. Biol. 2009, 385, 595.
         | Crossref | GoogleScholarGoogle Scholar | 19014950PubMed |

[72]  R. Battistutta, Cell. Mol. Life Sci. 2009, 66, 1868.
         | Crossref | GoogleScholarGoogle Scholar | 19387547PubMed |

[73]  N. F. Valadares, L. B. Salum, I. Polikarpov, A. D. Andricopulo, R. C. Garratt, J. Chem. Inf. Model. 2009, 49, 2606.
         | Crossref | GoogleScholarGoogle Scholar | 19863110PubMed |

[74]  Y. Lu, T. Shi, Y. Wang, H. Yang, X. Yan, X. Luo, H. Jiang, W. Zhu, J. Med. Chem. 2009, 52, 2854.
         | Crossref | GoogleScholarGoogle Scholar | 19358610PubMed |

[75]  P. Auffinger, F. A. Hays, E. Westhof, P. S. Ho, Proc. Natl. Acad. Sci. USA 2004, 101, 16789.
         | Crossref | GoogleScholarGoogle Scholar |

[76]  D. A. Kraut, M. J. Churchill, P. E. Dawson, D. Herschlag, ACS Chem. Biol. 2009, 4, 269.
         | Crossref | GoogleScholarGoogle Scholar | 19260691PubMed |

[77]  S. Álvarez, H. Khanwalkar, R. Alvarez, C. Erb, F. Rodriguez-Barrios, P. Germain, H. Gronemeyer, A. R. De Lera, ChemMedChem 2009, 4, 1630.
         | Crossref | GoogleScholarGoogle Scholar | 19670208PubMed |

[78]  D. Lévesque, J.-D. Beuudoin, S. Roy, J.-P. Perreault, Biochem. J. 2007, 403, 129.
         | Crossref | GoogleScholarGoogle Scholar | 17163839PubMed |

[79]  A. R. Voth, P. Khuu, K. Oishi, P. S. Ho, Nat. Chem. 2009, 1, 74.
         | Crossref | GoogleScholarGoogle Scholar |

[80]  S. D. Gilbert, F. E. Reyes, A. L. Edwards, R. T. Batey, Structure 2009, 17, 857.
         | Crossref | GoogleScholarGoogle Scholar | 19523903PubMed |

[81]  V. Fritsch, E. Westhof, Structure 2009, 17, 784.
         | Crossref | GoogleScholarGoogle Scholar | 19523895PubMed |

[82]  Y.-X. Lu, J.-W. Zou, J.-C. Fan, W.-N. Zhao, Y.-J. Jiang, Q.-S. Yu, J. Comput. Chem. 2009, 30, 725.
         | Crossref | GoogleScholarGoogle Scholar | 18727160PubMed |

[83]  R. Battistutta, M. Mazzorana, S. Sarno, Z. Kazimierczuk, G. Zanotti, L. A. Pinna, Chem. Biol. 2005, 12, 1211.
         | Crossref | GoogleScholarGoogle Scholar | 16298300PubMed |

[84]  Y. Lu, Y. Wang, Z. Xu, X. Yan, X. Luo, H. Jiang, W. Zhu, J. Phys. Chem. B 2009, 113, 12615.
         | Crossref | GoogleScholarGoogle Scholar | 19708644PubMed |

[85]  A. R. Voth, F. A. Hays, P. S. Ho, Proc. Natl. Acad. Sci. USA 2007, 104, 6188.
         | Crossref | GoogleScholarGoogle Scholar |