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Volumn 3, Issue 5, 2008, Pages 868-880

Van der Waals and polar intermolecular contact distances: Quantifying supramolecular synthons

Author keywords

Atomic radii; Benzene; Crystal engineering; Supramolecular chemistry; Van der Waals radii

Indexed keywords


EID: 54849427511     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700343     Document Type: Article
Times cited : (43)

References (86)
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    • an important paper: b) E. G. Cox, Rev. Mod. Phys. 1958, 30, 159-162;
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    • the standard reference for the experimental crystal structure of benzene is almost surely the low-temperature neutron determination: c G. E. Bacon, N. A. Curry, S. A. Wilson, Proc. R. Soc. London Ser. A 1964, 279, 98-110
    • the standard reference for the experimental crystal structure of benzene is almost surely the low-temperature neutron determination: c) G. E. Bacon, N. A. Curry, S. A. Wilson, Proc. R. Soc. London Ser. A 1964, 279, 98-110.
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    • Here direction means any local anisotropy in the crystal packing
    • Here "direction" means any local anisotropy in the crystal packing.
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    • It is impossible to survey the almost-oceanic amount of crystal-engineering literature, which deals with these molecular-to-crystal- structure correlations. However, the following recent reviews could be a good entry into this literature: a Frontiers in Crystal Engineering (Eds.: E. R. Tiekink, J. J. Vittal), Wiley, Chichester, 2005;
    • It is impossible to survey the almost-oceanic amount of crystal-engineering literature, which deals with these molecular-to-crystal- structure correlations. However, the following recent reviews could be a good entry into this literature: a) Frontiers in Crystal Engineering (Eds.: E. R. Tiekink, J. J. Vittal), Wiley, Chichester, 2005;
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    • A general description of CSP in the context of a crystal structure as an emergent property of a molecule: a) G. R. Desiraju, Curr. Sci. 2005, 88, 374 -380;
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    • Once again, the literature on the importance of weak interactions in biological systems is vast, and no attempt can be made to survey this comprehensively; see, however: a M. Brandl, M. S. Weiss, A. Jabs, J. Sühnel, R. Hilgenfeld, J. Mol. Biol. 2001, 307, 357-377;
    • Once again, the literature on the importance of weak interactions in biological systems is vast, and no attempt can be made to survey this comprehensively; see, however: a) M. Brandl, M. S. Weiss, A. Jabs, J. Sühnel, R. Hilgenfeld, J. Mol. Biol. 2001, 307, 357-377;
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    • The structure of a solid may be specified either with standard crystallographic information (primary coordinates) or with interatomic distances (secondary coordinates). The use of the latter type of information is not common in crystal engineering and structural chemistry. However, for an interesting early paper in this regard that emphasizes the equivalence of interaction complementarity with space (i.e., distance) complementarity, see: a) J. M. A. Robinson, B. M. Kariuki, K. D. M. Harris, D. Philp, J. Chem. Soc. Perkin Trans. 2 1998, 2, 2459-2469;
    • The structure of a solid may be specified either with standard crystallographic information (primary coordinates) or with interatomic distances (secondary coordinates). The use of the latter type of information is not common in crystal engineering and structural chemistry. However, for an interesting early paper in this regard that emphasizes the equivalence of interaction complementarity with space (i.e., distance) complementarity, see: a) J. M. A. Robinson, B. M. Kariuki, K. D. M. Harris, D. Philp, J. Chem. Soc. Perkin Trans. 2 1998, 2, 2459-2469;
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    • another approach that also relates intermolecular distances with interaction type uses the Hirshfeld surfaces: b) J. J. McKinnon, M. A. Spackman, A. S. Mitchell, Acta Crystallogr. Sect. A 2004, 60, 627-668;
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    • The Gordian knot is an intricate knot that Gordius of Phrygia in ancient Greece used to tie his oxcart. Cutting the Gordian knot is to solve a seemingly intractable problem by a bold stroke. The legend goes that an oracle foretold that whoever unraveled the knot would become the king of Asia. Alexander the Great, who had this ambition, unraveled it by simply cutting it with his sword. This is not cheating as one might surmise, but followed from Alexander's conviction that if the knot could not be unraveled, it could not have had any free ends; see: K. Devlin, Untying the Gordian Knot, to be found under, 2001
    • The Gordian knot is an intricate knot that Gordius of Phrygia in ancient Greece used to tie his oxcart. Cutting the Gordian knot is to solve a seemingly intractable problem by a bold stroke. The legend goes that an oracle foretold that whoever unraveled the knot would become the king of Asia. Alexander the Great, who had this ambition, unraveled it by simply cutting it with his sword. This is not "cheating" as one might surmise, but followed from Alexander's conviction that if the knot could not be unraveled, it could not have had any free ends; see: K. Devlin, "Untying the Gordian Knot", to be found under http://www.maa.org/devlin/devlin_9_01.html, 2001.
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    • P. Ganguly, unpublished results; a summary of these results is given in Appendix1.
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    • 4/3/2 in the equation may be treated as empirical.
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    • We use inverted commas to indicate that we are using these descriptors for the first time in this paper and that the meanings of the terms may be slightly different from conventional usage. We do not wish to add new terminology unnecessarily to this discussion
    • We use inverted commas to indicate that we are using these descriptors for the first time in this paper and that the meanings of the terms may be slightly different from conventional usage. We do not wish to add new terminology unnecessarily to this discussion.
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    • there is much literature on this topic subsequent to this original paper; for a recent review, see: b B. K. Saha, A. Nangia, Heteroat. Chem. 2007, 18, 185 -194;
    • there is much literature on this topic subsequent to this original paper; for a recent review, see: b) B. K. Saha, A. Nangia, Heteroat. Chem. 2007, 18, 185 -194;
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    • the idea that a halogen atom has an anisotropic radius is not new; see, for example: c) S. C. Nyburg, C. H. Faerman, Acta Crystallogr. Sect. A 1987, 43, 106 -110;
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    • V. M. Goldschmidt invoked the idea of a building block in defining these structural domains and stated that if a member of an isomorphous series is constructed of building blocks whose size and polarization properties lie near the limit which the structure of this series can accommodate, changes in the thermodynamic environment may cause this limit to be exceeded and a new structure to be developed. This idea is mentioned and credited to Goldschmidt (but not cited) by: M. J. Buerger, M. C. Bloom, Z. Kristallogr., 1937, 96, 182-200; we suggest that, similarly, changes in the chemical environment may also cause the structural limit to be exceeded.
    • V. M. Goldschmidt invoked the idea of a building block in defining these structural domains and stated that "if a member of an isomorphous series is constructed of building blocks whose size and polarization properties lie near the limit which the structure of this series can accommodate, changes in the thermodynamic environment may cause this limit to be exceeded and a new structure to be developed". This idea is mentioned and credited to Goldschmidt (but not cited) by: M. J. Buerger, M. C. Bloom, Z. Kristallogr., 1937, 96, 182-200; we suggest that, similarly, changes in the chemical environment may also cause the structural limit to be exceeded.
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    • This is essentially the most primitive aspect of vacuum-polarization techniques in quantum electrodynamics; for a description, see: B. Hayes, Am. Sci. 2004, 92, 212, 216
    • This is essentially the most primitive aspect of vacuum-polarization techniques in quantum electrodynamics; for a description, see: B. Hayes, Am. Sci. 2004, 92, 212 - 216.


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