Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH FRONT

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 |

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

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

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

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

[6]  R. F. Stewart, Chem. Phys. Lett. 1979, 65, 335.
         | CrossRef |

[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 |

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

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

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

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

[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 | 20361346PubMed |

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

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

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

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

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

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

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

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

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

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

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

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

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

[28]  P. Politzer, J. S. Murray, M. C. Concha, J. Mol. Model. 2008, 14, 659.
         | CrossRef | 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 | 17444706PubMed |

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

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

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

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

[34]  M. Palusiak, J. Mol. Struct. Theochem. 2010, 945, 89.
         | CrossRef |

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

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

[37]  K. Hermansson, J. Phys. Chem. A 2002, 106, 4695.
         | CrossRef |

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

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

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

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

[42]  E. D. Stevens, Mol. Phys. 1979, 37, 27.
         | CrossRef |

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

[44]  S. Ikuta, J. Mol. Struct. Theochem. 1990, 205, 191.
         | CrossRef |

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

[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 |

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

[49]  S. C. Nyburg, Acta Cryst. 1979, A35, 641.
         | CrossRef |

[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 |
      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 |

[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 |

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

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

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

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

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

[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 | 11686715PubMed |

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

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

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

[65]  K. Rissanen, CrystEngComm 2008, 10, 1107.
         | CrossRef |

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

[67]  A. Forni, J. Phys. Chem. A 2009, 113, 3403.
         | CrossRef | 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 | 19593826PubMed |

[69]  Y. Lu, Y. Wang, W. Zhu, Phys. Chem. Chem. Phys. 2010, 12, 4543.
         | CrossRef | 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 |

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

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

[73]  N. F. Valadares, L. B. Salum, I. Polikarpov, A. D. Andricopulo, R. C. Garratt, J. Chem. Inf. Model. 2009, 49, 2606.
         | CrossRef | 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 | 19358610PubMed |

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

[76]  D. A. Kraut, M. J. Churchill, P. E. Dawson, D. Herschlag, ACS Chem. Biol. 2009, 4, 269.
         | CrossRef | 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 | 19670208PubMed |

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

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

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

[81]  V. Fritsch, E. Westhof, Structure 2009, 17, 784.
         | CrossRef | 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 | 18727160PubMed |

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

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

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



Rent Article (via Deepdyve) Export Citation Cited By (161)