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Chirality Codes and Molecular Structure

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REQUIMTE, CQFB, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Quinta da Torre, 2829-516 Caparica, Portugal, Computer-Chemie-Centrum, Institute of Organic Chemistry, University of Erlangen-Nürnberg, Nägelsbachstrasse 25, D-91052 Erlangen, Germany, and Faculty of Science, University of Kragujevac, P.O. Box 60, 34000 Kragujevac, Serbia and Montenegro
Cite this: J. Chem. Inf. Comput. Sci. 2004, 44, 3, 831–836
Publication Date (Web):February 21, 2004
https://doi.org/10.1021/ci030410h
Copyright © 2004 American Chemical Society

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    Abstract

    Some time ago a structure-descriptor, named “chirality code”, was put forward [J. Chem. Inf. Comput. Sci.2001, 41, 369−375], aimed at distinguishing between enantiomers. The chirality code is a sequence of (typically 100) numbers, being equal to the value of a certain “chirality function” at equidistant points within a chosen interval. For molecules of moderate size the chirality function has thousands of peaks (maxima and minima), one for each quartet of atoms. Therefore it looks as if the chirality code cannot provide a faithful representation of the chirality function and thus a faithful representation of the molecular structure. We now show that functional groups present in the molecule result in clusters of near-lying and partially overlapping peaks, whose position in the chirality code is characteristic for the particular functional group. This enables a sound structural interpretation of the chirality code.

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     Universidade Nova de Lisboa.

     University of Erlangen-Nürnberg.

    *

     Corresponding author phone:  ++381-34-331-876; fax:  ++381-34-335-040; e-mail:  [email protected].

    §

     University of Kragujevac.

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