Application of molecular topology for the prediction of the reaction times and yields under solvent-free conditions

Ball milling and conventional magnetic stirring can be used to support different laboratory techniques with a highly efficient mixing of reagents under solvent-free conditions. By using multilinear regression and linear discriminant analysis, topological-mathematical models have been built to predict the yield and the reaction time for organocatalytic reactions, Suzuki reactions and reactions of synthesis of heterocyclic compounds. The results from the in silico predictions confirm the usefulness of the approach followed.

[1]  Fumio Toda,et al.  SOLID STATE ORGANIC CHEMISTRY : EFFICIENT REACTIONS, REMARKABLE YIELDS, AND STEREOSELECTIVITY , 1995 .

[2]  Subhash C. Basak,et al.  Prediction of Mutagenicity of Aromatic and Heteroaromatic Amines from Structure: A Hierarchical QSAR Approach , 2001, J. Chem. Inf. Comput. Sci..

[3]  G. M. Furnival.  All Possible Regressions with Less Computation , 1971 .

[4]  Sara Mashkouri,et al.  Mechanochemical Solvent-Free and Catalyst-Free One-Pot Synthesis of Pyrano[2,3-d]Pyrimidine-2,4(1H,3H)-Diones with Quantitative Yields , 2009, Molecules.

[5]  Jorge Gálvez,et al.  Charge Indexes. New Topological Descriptors , 1994, J. Chem. Inf. Comput. Sci..

[6]  R. R. Hocking.  Criteria for Selection of a Subset Regression: Which One Should Be Used? , 1972 .

[7]  R. García-Domenech,et al.  Some new trends in chemical graph theory. , 2008, Chemical reviews.

[8]  Alexandru T. Balaban,et al.  Topological indices based on topological distances in molecular graphs , 1983 .

[9]  R. García-Domenech,et al.  Virtual combinatorial syntheses and computational screening of new potential anti-herpes compounds. , 1999, Journal of medicinal chemistry.

[10]  Alexander Golbraikh,et al.  Novel ZE-Isomerism Descriptors Derived from Molecular Topology and Their Application to QSAR Analysis , 2002, J. Chem. Inf. Comput. Sci..

[11]  L B Kier,et al.  General definition of valence delta-values for molecular connectivity. , 1983, Journal of pharmaceutical sciences.

[12]  Oskar Axelsson,et al.  The Suzuki Reaction Under Solvent-Free Conditions , 2000 .

[13]  P. Moran.  Notes on continuous stochastic phenomena. , 1950, Biometrika.

[14]  Carsten Bolm,et al.  A highly efficient asymmetric organocatalytic aldol reaction in a ball mill. , 2007, Chemistry.

[15]  Francisco Torrens,et al.  Bond‐based 3D‐chiral linear indices: Theory and QSAR applications to central chirality codification , 2008, J. Comput. Chem..

[16]  Ivan Gutman,et al.  Modeling Boiling Points of Cycloalkanes by Means of Iterated Line Graph Sequences , 2001, J. Chem. Inf. Comput. Sci..

[17]  J. Gálvez,et al.  Prediction of properties of chiral compounds by molecular topology. , 1998, Journal of molecular graphics & modelling.

[18]  C. Bolm,et al.  Organocatalytic reactions: effects of ball milling, microwave and ultrasound irradiation , 2008 .

[19]  A. Balaban.  Highly discriminating distance-based topological index , 1982 .

[20]  Emili Besalú,et al.  Fast Computation of Cross-Validated Properties in Full Linear Leave-Many-Out Procedures , 2001 .