Steric effects vs. electron delocalization: a new look into stability of diastereomers, conformers and constitutional Isomers

Abstract

<div>A quantum chemical investigation of the stability of compounds with identical formulas was carried out on 23 classes of halogenated compounds made of H, F, Cl, Br, I, C, N, P, O and S atoms. The prevalence of formula in which its Z configuration, gauche conformation and meta isomer are the most stable forms is calculated and discussed. The prevalence data shows that in compounds made of carbon backbones, the electronic effect is weaker than the steric effect. The electronic factor is more important as the backbone atoms are replaced with atoms on the right and upper part of the periodic table.</div>

Z-Matrix template-based substitution approach for enumeration of 3D molecular structures

“…The approach has been used to study many classes of compounds from a simple and small class of molecules such as ethane and ethene to larger and more complex structures such as dioxin-like compounds [11][12][13][14][15]. The substitution scheme in the template can lead to different compounds of the same class, constitutional isomers, configurational isomers and conformational isomers.…”

“…Chemists, by their manual intuition and labour, have been able to identify template structures and substitution points for the combinatorial investigation of compounds. Inspired by the use of this approach in DDT analogues [5], we successfully applied it to 26 classes of compounds to exhaustively generate over ten thousand 3D structures for further investigation by quantum chemical methods [11][12][13][14][15]. Based on these previous reports, this is our first paper devoted to the methodology of generic structure generation using Z-matrix template-based substitution.…”

Z-Matrix template-based substitution approach for enumeration of 3D molecular structures

“…The approach has been used to study many classes of compounds from a simple and small class of molecules such as ethane and ethene to larger and more complex structures such as dioxin-like compounds [11][12][13][14][15]. The substitution scheme in the template can lead to different compounds of the same class, constitutional isomers, configurational isomers and conformational isomers.…”

“…Chemists, by their manual intuition and labour, have been able to identify template structures and substitution points for the combinatorial investigation of compounds. Inspired by the use of this approach in DDT analogues [5], we successfully applied it to 26 classes of compounds to exhaustively generate over ten thousand 3D structures for further investigation by quantum chemical methods [11][12][13][14][15]. Based on these previous reports, this is our first paper devoted to the methodology of generic structure generation using Z-matrix template-based substitution.…”