Abstract
Prior to van’t Hoff and Le Bel, chemistry was two-dimensional. Since 1874, however, we have had to deal with the third dimension in molecular models, projection formulae, configurational descriptors and, most recently, computer algorithms used to describe and specify configuration. The problem is complicated because chirality, an important aspect of three-dimensional structure, is an attribute of the molecule as a whole whereas the commonly used Cahn-Ingold-Prelog configurational descriptors require factorisation of chirality into individual chiral elements. This paper deals with the history of chirality and the present status of describing it.
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After the present conference ended, the author learned (Ricketts, D.M. personal communication, June 7, 1990) that program COBRA, marketed by Oxford Molecular, can generate multiple low-energy conformations from two-dimensional constitutional formula. The problem remains that if all low-energy conformations are stored, the database may become excessively large; if, on the other hand, the multiple conformation search is carried out ‘on the fly’ (the conformations are generated as the search proceeds) the demand for CPU capacity may be excessive.
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Eliel, E.L. (1993). Chemistry in Three Dimensions. In: Warr, W.A. (eds) Chemical Structures 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-78027-1_1
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DOI: https://doi.org/10.1007/978-3-642-78027-1_1
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