Molecular size and molecular structure: Discriminating their changes upon chemical reactions in terms of information entropy

Kerber, 2004, Molecules in silico: the generation of structural formulae and its applications, J. Comput. Chem. Jpn., 3, 95, 10.2477/jccj.3.85 Barigye, 2014, Trends in information theory-based chemical structure codification, Mol. Divers., 18, 673, 10.1007/s11030-014-9517-7 Shen, 2021, Automation and computer-assisted planning for chemical synthesis, Nature Reviews Methods Primers, 1, 23, 10.1038/s43586-021-00022-5 Matsubara, 2021, Digitization of organic synthesis — how Synthetic organic chemists use AI technology, Chem. Lett., 50, 475, 10.1246/cl.200802 Bonchev, 1995, Kolmogorov's information, shannon's entropy, and topological complexity of molecules, Bulg. Chem. Commun., 28, 567 Varnek, 2011, Chemoinformatics as a theoretical chemistry discipline, Mol. Inf., 30, 20, 10.1002/minf.201000100 Trinajstić, 2002, Mathematical chemistry, Croat. Chem. Acta, 75, 329 Basak, 1997, Use of topostructural, topochemical, and geometric parameters in the prediction of vapor pressure:A Hierarchical QSAR approach, J. Chem. Inf. Comput. Sci., 37, 651, 10.1021/ci960176d Sabirov, 2015, Information entropy of fullerenes, J. Chem. Inf. Model., 55, 1576, 10.1021/acs.jcim.5b00334 Fischer, 2021, Interfacial informatics, J. Phys. Materials., 4, 10.1088/2515-7639/ac10a9 Sabirov, 2016, Activation energies and information entropies of helium penetration through fullerene walls. Insights into the formation of endofullerenes nX@C60/70 (n = 1 and 2) from the information entropy approach, RSC Adv., 6, 72230, 10.1039/C6RA12228K Sabirov, 2016, Information entropy of interstellar and circumstellar carbon-containing molecules: molecular size against structural complexity, Comput. Theor. Chem., 1097, 83, 10.1016/j.comptc.2016.10.014 Bertz, 2003, Complexity of synthetic reactions. The use of complexity indices to evaluate reactions, transforms and disconnections, New J. Chem., 27, 860, 10.1039/b210843g Sabirov, 2018, Information entropy changes in chemical reactions, Comput. Theor. Chem., 1123, 169, 10.1016/j.comptc.2017.11.022 Sabirov, 2020, Information entropy of mixing molecules and its application to molecular ensembles and chemical reactions, Comput. Theor. Chem., 1187, 112933, 10.1016/j.comptc.2020.112933 Böttcher, 2016, An additive definition of molecular complexity, J. Chem. Inf. Model., 56, 462, 10.1021/acs.jcim.5b00723 Karreman, 1955, Topological information content and chemical reactions, Bull. Math. Biophys., 17, 279, 10.1007/BF02477754 Smolenskii, 2011, Digital chemistry. Molecular numbers and digital indices of chemical reactions, Dokl. Chem., 437, 651, 10.1134/S0012500811040100 Corey, 1995, 465 Bertz, 1981, The first general index of molecular complexity, J. Am. Chem. Soc., 103, 3599, 10.1021/ja00402a071 Böttcher, 2017, From molecules to life: quantifying the complexity of chemical and biological systems in the universe, J. Mol. Evol., 86, 1, 10.1007/s00239-017-9824-6 Sabirov, 2021, Information entropy of regular dendrimer aggregates and irregular intermediate structures, Liquids, 1, 25, 10.3390/liquids1010002 Shannon, 1948, A mathematical theory of communication, Bell Sys, Tech. J., 27, 379 Bonchev, 1976, Symmetry and information content of chemical structures, Bull. Math. Biol., 3, 119, 10.1007/BF02471752 Dehmer, 2011, A history of graph entropy measures, Inf. Sci., 181, 57, 10.1016/j.ins.2010.08.041 Sabirov, 2020, Classification of isentropic molecules in terms of Shannon entropy, EPJ Web Conf., 244, 10.1051/epjconf/202024401016 Ugi, 1971, Representation of chemical systems and interconversions by be matrices and their transformation properties, Angew. Chem., Int. Ed. Engl., 10, 914, 10.1002/anie.197109141 Nielsen, 2001, 822 Nandi, 2017, A tabu-search based strategy for modeling molecular aggregates and binary reactions, Comput. Theor. Chem., 1111, 69, 10.1016/j.comptc.2017.03.040 Sabirov, 2020, Fullerene–1,4-dioxane adducts: a DFT study of the structural features and molecular properties, Fullerenes, Nanotub. Carbon Nanostruct., 28, 154, 10.1080/1536383X.2019.1680984 Sabirov, 2021, Information entropy in chemistry: an overview, Entropy, 23, 1240, 10.3390/e23101240