Finding the direct energy-structure correlations in intramolecular aromaticity assisted hydrogen bonding (AAHB)
| Autor: | Marek Lozynski, Danuta Rusinska-Roszak |
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| Rok vydání: | 2021 |
| Předmět: |
Complete data
Materials science 010405 organic chemistry Hydrogen bond Hydrogen Bonding Aromaticity 010402 general chemistry 01 natural sciences Computer Graphics and Computer-Aided Design Bond order 0104 chemical sciences chemistry.chemical_compound chemistry Computational chemistry Molecular descriptor Intramolecular force Materials Chemistry Quantum Theory Pyrene Physical and Theoretical Chemistry Energy structure Spectroscopy |
| Zdroj: | Journal of Molecular Graphics and Modelling. 105:107884 |
| ISSN: | 1093-3263 |
| DOI: | 10.1016/j.jmgm.2021.107884 |
| Popis: | A predictive model for intramolecular hydrogen bond energy (EHB) calculation of polyaromatic ortho-hydroxyaldehydes based on a set of small, functionalized hydrocarbons is developed. The complete data set of 18 compounds was used for this study. The model is based on one of four optional categories of molecular descriptors: geometric, spectroscopic, bond order and topological indices. The model of Wiberg bond indices (WBIs) as descriptors of the C C involved bond based on stepwise regression has acceptable prediction abilities for 14 structures of ortho-hydroxyformylobenzo[a]pyrene derivatives already at the semiempirical level. The presented correlation enables a significantly more rapid and quantitative description of the hydrogen bonding strength than the much more time-consuming MTA method. Thus, WBIs are shown to provide a reliable means for fast prescreening of the energy of chelate hydrogen bonds potentially for any polyaromatic derivatives. |
| Databáze: | OpenAIRE |
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