Exhaustive Generation of Organic Isomers, 4. Acyclic Stereoisomers with One or More Chiral Carbon Atoms

A stereochemical computer assisted molecular generation and counting system, S-CAMGEC, based on graph theory has been created for the exhaustive and nonredundant generation of ( R ) and (5') carbon stereoisomers of acyclic compounds, which may contain heteroatoms of different valences and multiple bonds. The program takes constitutional N-tuples, searches and labels chiral centers, searches for symmetry, assigns priorities according to Cahn, Ingold, and Prelog rules, and generates stereoisomers in excellent agreement with results coming from reported enumeration procedures. For that a new molecular code was created which defines each stereoisomer in a single and unique way shown through several examples.

[2]  Nenad Trinajstić,et al.  Computer enumeration and generation of trees and rooted trees , 1981, J. Chem. Inf. Comput. Sci..

[3]  H. Henze,et al.  THE NUMBER OF ISOMERIC HYDROCARBONS OF THE METHANE SERIES , 1931 .

[4]  Alexandru T. Balaban,et al.  Chemical graphs—XII: Configurations of annulenes , 1971 .

[5]  L. Klasinc,et al.  Computer enumeration of substituted polyhexes , 1984, Comput. Chem..

[6]  M. Leonor Contreras,et al.  Exhaustive generation of organic isomers. 2. Cyclic structures: new compact molecular code , 1992, J. Chem. Inf. Comput. Sci..

[7]  Jianji Wang,et al.  Enumeration of isomers of polyethers , 1991, J. Chem. Inf. Comput. Sci..

[8]  Hidetsugu Abe,et al.  A computer program for generation of constitutionally isomeric structural formulas , 1984, Journal of chemical information and computer sciences.

[9]  Robert W. Robinson,et al.  The numbers of chiral and achiral alkanes and monosubstituted alkanes , 1976 .

[10]  M. Leonor Contreras,et al.  Exhaustive Generation of Organic Isomers. 3. Acyclic, Cyclic, and Mixed Compounds , 1994, J. Chem. Inf. Comput. Sci..

[11]  Tatsuya Akutsu.  A new method of computer representation of stereochemistry. Transforming a stereochemical structure into a graph , 1991, J. Chem. Inf. Comput. Sci..

[12]  J. H. Redfield,et al.  The Theory of Group-Reduced Distributions , 1927 .

[13]  M. Leonor Contreras,et al.  Exhaustive generation of organic isomers. 1. Acyclic structures , 1992, J. Chem. Inf. Comput. Sci..

[14]  Kimito Funatsu,et al.  Further development of structure generation in the automated structure elucidation system CHEMICS , 1988, J. Chem. Inf. Comput. Sci..

[15]  G. Pólya.  Kombinatorische Anzahlbestimmungen für Gruppen, Graphen und chemische Verbindungen , 1937 .