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Flexible heuristic algorithm for automatic molecule fragmentation: application to the UNIFAC group contribution model

A priori calculation of thermophysical properties and predictive thermodynamic models can be very helpful for developing new industrial processes. Group contribution methods link the target property to contributions based on chemical groups or other molecular subunits of a given molecule. However, t...

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Autor principal: Müller, Simon
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer International Publishing 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6701077/
https://www.ncbi.nlm.nih.gov/pubmed/33430960
http://dx.doi.org/10.1186/s13321-019-0382-3
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author Müller, Simon
author_facet Müller, Simon
author_sort Müller, Simon
collection PubMed
description A priori calculation of thermophysical properties and predictive thermodynamic models can be very helpful for developing new industrial processes. Group contribution methods link the target property to contributions based on chemical groups or other molecular subunits of a given molecule. However, the fragmentation of the molecule into its subunits is usually done manually impeding the fast testing and development of new group contribution methods based on large databases of molecules. The aim of this work is to develop strategies to overcome the challenges that arise when attempting to fragment molecules automatically while keeping the definition of the groups as simple as possible. Furthermore, these strategies are implemented in two fragmentation algorithms. The first algorithm finds only one solution while the second algorithm finds all possible fragmentations. Both algorithms are tested to fragment a database of 20,000+ molecules for use with the group contribution model Universal Quasichemical Functional Group Activity Coefficients (UNIFAC). Comparison of the results with a reference database shows that both algorithms are capable of successfully fragmenting all the molecules automatically. Furthermore, when applying them on a larger database it is shown, that the newly developed algorithms are capable of fragmenting structures previously thought not possible to fragment. [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1186/s13321-019-0382-3) contains supplementary material, which is available to authorized users.
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spelling pubmed-67010772019-08-26 Flexible heuristic algorithm for automatic molecule fragmentation: application to the UNIFAC group contribution model Müller, Simon J Cheminform Research Article A priori calculation of thermophysical properties and predictive thermodynamic models can be very helpful for developing new industrial processes. Group contribution methods link the target property to contributions based on chemical groups or other molecular subunits of a given molecule. However, the fragmentation of the molecule into its subunits is usually done manually impeding the fast testing and development of new group contribution methods based on large databases of molecules. The aim of this work is to develop strategies to overcome the challenges that arise when attempting to fragment molecules automatically while keeping the definition of the groups as simple as possible. Furthermore, these strategies are implemented in two fragmentation algorithms. The first algorithm finds only one solution while the second algorithm finds all possible fragmentations. Both algorithms are tested to fragment a database of 20,000+ molecules for use with the group contribution model Universal Quasichemical Functional Group Activity Coefficients (UNIFAC). Comparison of the results with a reference database shows that both algorithms are capable of successfully fragmenting all the molecules automatically. Furthermore, when applying them on a larger database it is shown, that the newly developed algorithms are capable of fragmenting structures previously thought not possible to fragment. [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1186/s13321-019-0382-3) contains supplementary material, which is available to authorized users. Springer International Publishing 2019-08-20 /pmc/articles/PMC6701077/ /pubmed/33430960 http://dx.doi.org/10.1186/s13321-019-0382-3 Text en © The Author(s) 2019 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.
spellingShingle Research Article
Müller, Simon
Flexible heuristic algorithm for automatic molecule fragmentation: application to the UNIFAC group contribution model
title Flexible heuristic algorithm for automatic molecule fragmentation: application to the UNIFAC group contribution model
title_full Flexible heuristic algorithm for automatic molecule fragmentation: application to the UNIFAC group contribution model
title_fullStr Flexible heuristic algorithm for automatic molecule fragmentation: application to the UNIFAC group contribution model
title_full_unstemmed Flexible heuristic algorithm for automatic molecule fragmentation: application to the UNIFAC group contribution model
title_short Flexible heuristic algorithm for automatic molecule fragmentation: application to the UNIFAC group contribution model
title_sort flexible heuristic algorithm for automatic molecule fragmentation: application to the unifac group contribution model
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6701077/
https://www.ncbi.nlm.nih.gov/pubmed/33430960
http://dx.doi.org/10.1186/s13321-019-0382-3
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