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RE: Discussion #2
- To: Chemical information in core CIF <corecifchem@iucr.org>
- Subject: RE: Discussion #2
- From: "Herbert J. Bernstein" <yaya@bernstein-plus-sons.com>
- Date: Mon, 1 Dec 2003 20:58:24 -0500
- In-Reply-To: <E88024C0BA8052478C717D472F978C18014E02AB@iu-mssg-mbx05.exchange.iu.edu>
- References: <E88024C0BA8052478C717D472F978C18014E02AB@iu-mssg-mbx05.exchange.iu.edu>
How about this approach -- instead of trying to agree on a definition of a molecule, should we not be trying to clearly state a reasonable set of chemical views of matter and, where possible the relationships snd/or transormations among those views, as has already been started for macromolecules. The graph-based approaches, chemical formulae, 3-D structures, charge density maps, residue-based polymeric descriptions, all have something to say about have various chemical entities can interact with other chemical entities, which is, after all, what Chemistry is all about. -- Herbert At 5:47 PM -0500 12/1/03, Bollinger, John Clayton wrote: >David Brown wrote: > >[...] > >> HDF, coming at this problem from a different direction, >> expressed shock at the thought that the chemists have no >> unique way of defining a molecule. >> >> From what I learned at the workshop, chemists not only >> have no unique way of defining a molecule, they don't even >> care! Most of the ontologies >> (dictionaries) being developed in chemistry are, like CIF, closely >> related to >> an experimental technique where the question of defining a >> molecule is not important. Peter Murray-Rust's CML defines a >> molecule as a composed of >> atoms, >> but leaves it to the author to state which atoms. Miloslav >> Nic in Prague is developing GTML (Graph Theory Mark-up >> Language) which can be used for molecular descriptions, but >> this also assumes that the molecular graph is already known. > >[...] > >> properties. The use of graph theory separates out the >> intrinsically chemical concepts from the graph theoretical >> description that can be manipulated mathematically. >> >> The bond graph represents a chemical interpretation of >> the 3D geometry, i.e., the geometry tells us which atoms are >> neighbours but not where the >> bonds >> are to be found. The bonds are assigned by applying various rules >> relating to >> the chemical properties of the atoms. However, not all bonds >> are of equal value; some are clearly stronger than others, >> i.e., they survive many of the physical and chemical >> treatments we can subject them to such as melting or >> dissolution in a solvent. Weaker bonds do not survive this >> treatment. > > We can > > thus imagine that each of the possible edges in the graph is > > associated > > with a > > number representing its 'strength'. (The 'strength' would be > > zero for the edges that could not possibly represent a >> chemical bond). I will >> deliberately >> avoid defining in detail what I mean by 'strength', but >> qualitatively it represents the number of electron pairs >> associated with the bond and it >> obeys >> (by definition in some treatments) the rule that the sum of >> the bond 'strengths' received by any atom is equal to the >> number of valence electrons the atom uses for bonding. >> (Implicit in this description is the notion >> that a >> bond 'strength' is not restricted to integer values). For >> over a century chemists have struggled to find a tight >> quantitative definition for bond 'strength' under such names >> as bond order, bond number, bond valence, electrostatic bond >> strength, etc., each definition trying to capture the concept >> in numeric form. All of these definitions are incomplete in >> one way or another, but in principle they allow us to order >> the bonds from strongest to weakest. Assuming that we can at >> least determine this order even if we cannot assign actual >> numbers to the bond 'strength', our problem then >> reduces >> to the question of where to place the cut-off between the >> bonds that are >> shown >> on the graph and those that are omitted. > >[...] > >> Before we try to define CIF items for particular chemical >> concepts, we need to have a consensus about the definition of >> a molecule. I have >> made some >> suggestions above, and I would be interested in people's >> comments. Is graph theory a fruitful way to go or should we >> take a different approach? > > What are >> the problems we might encounter using the approach described above? > >I find the idea of relating chemical properties to a bond graph to be >rather attractive, although I confess to the influence of a bit of >background in formal mathematics. > >One aspect that David left unexplored is the possibility of applying >multiple properties to bond graph edges. One need not choose a single >measure of bond strength, nor make measures of bond strength the only >properties a bond graph edge may have. For instance, one could apply an >explicit bond categorization (e.g. "covalent", "dative", "hydrogen >bond", "non-bond"). One could also express purely chemical information, >such as the fact that "this is the bond that is broken in the course of >the von Foo reaction". CIF is conveniently flexible in this regard, as >authors may include exactly the properties they wish to describe while >ignoring all others. > >One oddity I see with that approach is that the interatomic distances >currently described by _geom_bond_distance fit nicely into the >collection of properties that could be associated with bond graph edges, >but many other _geom_* items do not. Graph theorists do have concepts >that could be applied there, but we must take care to avoid making CIF >(more) incomprehensible to mere mortals. Perhaps, though, it does make >sense to consider whether all the various geom_* categories should be >subsumed into a scheme such as this -- they are all examples of data >that have both crystallographic significance and chemical significance. > >As chemists in general have no single consistent definition of a >molecule, it would be fruitless for us to attempt to impose a universal >one of our own in hopes of satisfying everyone. The alternatives I see >are > >(1) to choose our own definition for CIF purposes and use it >consistently; >(2) to support diverse CIF items with which to describe multiple >different molecule concepts; >(3) to provide sufficient data for a chemist to apply his or her own >definition of "molecule"; or >(4) to attempt to ignore molecules altogether. > >Although (4) is perhaps most true to pure crystallography, I think it is >least suitable for our purpose. Option (2) strikes me as inelegant and >short-sighted. Option (1) might be feasible if we could actually come >up with a suitable definition, but I question whether that is possible. >That leaves option (3), to which category I would assign most >applications of the bond graph approach that I have imagined so far. > > >John Bollinger > >-- > >John C. Bollinger, Ph.D. >Indiana University >Molecular Structure Center > >jobollin@indiana.edu >_______________________________________________ >coreCIFchem mailing list >coreCIFchem@iucr.org >http://scripts.iucr.org/mailman/listinfo/corecifchem -- ===================================================== Herbert J. Bernstein, Professor of Computer Science Dowling College, Kramer Science Center, KSC 121 Idle Hour Blvd, Oakdale, NY, 11769 +1-631-244-3035 yaya@dowling.edu ===================================================== _______________________________________________ coreCIFchem mailing list coreCIFchem@iucr.org http://scripts.iucr.org/mailman/listinfo/corecifchem
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