Information entropy of mixing molecules and its application to molecular ensembles and chemical reactions

Shannon, 1948, A mathematical theory of communication, Bell. Syst. Tech. J., 27, 379, 10.1002/j.1538-7305.1948.tb01338.x Trucco, 1956, A note on the information content of graphs, Bull. Math. Biophys., 18, 129, 10.1007/BF02477836 Mowshowitz, 1968, Entropy and the complexity of graphs: I. An index of the relative complexity of a graph, Bull. Math. Biophys, 30, 175, 10.1007/BF02476948 Rashevsky, 1955, Life, information theory, and topology, Bull. Math. Biophys., 17, 229, 10.1007/BF02477860 Karreman, 1955, Topological information content and chemical reactions, Bull. Math. Biophys., 17, 279, 10.1007/BF02477754 Bonchev, 1976, Symmetry and information content of chemical structures, Bull. Math. Biol., 38, 119, 10.1016/S0092-8240(76)80029-8 Bertz, 1983, On the complexity of graphs and molecules, Bull. Math. Biol., 45, 849, 10.1016/S0092-8240(83)80030-5 Bonchev, 1995, Kolmogorov’s information, Shannon’s entropy, and topological complexity of molecules, Bulg. Chem. Commun., 28, 567 Bonchev, 1977, Information theory, distance matrix, and molecular branching, J. Chem. Phys., 67, 4517, 10.1063/1.434593 Bonchev, 1981, Isomer discrimination by topological information approach, J. Comput. Chem., 2, 127, 10.1002/jcc.540020202 Castellano, 2013, Classification of flavonoid compounds by using entropy of information theory, Phytochemistry, 93, 182, 10.1016/j.phytochem.2013.03.024 Castellano, 2014, Classification of stilbenoid compounds by entropy of artificial intelligence, Phytochemistry, 97, 62, 10.1016/j.phytochem.2013.10.010 Castellano, 2015, Information entropy-based classification of triterpenoids and steroids from Ganoderma, Phytochemistry, 116, 305, 10.1016/j.phytochem.2015.05.008 Zhdanov, 1979, Information Entropy in Organic Chemistry, Rostov University Dehmer, 2009, On entropy-based molecular descriptors: Statistical analysis of real and synthetic chemical structures, J. Chem. Inf. Model., 49, 1655, 10.1021/ci900060x Basak, 1984, Comparative study of lipophilicity versus topological molecular descriptors in biological correlations, J. Pharm. Sci., 73, 429, 10.1002/jps.2600730403 Basak, 1991, Predicting properties of molecules using graph invariants, J. Math. Chem., 7, 243, 10.1007/BF01200826 Barigye, 2014, Trends in information theory-based chemical structure codification, Mol. Divers., 18, 673, 10.1007/s11030-014-9517-7 Bonchev, 1997, Novel indices for the topological complexity of molecules, SAR QSAR Environ. Res., 7, 23, 10.1080/10629369708039123 Bertz, 1981, The first general index of molecular complexity, J. Am. Chem. Soc., 103, 3599, 10.1021/ja00402a071 S.H. Bertz, Complexity of synthetic reactions. The use of complexity indices to evaluate reactions, transforms and disconnections, New J. Chem. 27 (2003) 860. Böttcher, 2016, An additive definition of molecular complexity, J. Chem. Inf. Model., 56, 462, 10.1021/acs.jcim.5b00723 Böttcher, 2018, 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 Dehmer, 2011, A history of graph entropy measures, Inf. Sci., 181, 57, 10.1016/j.ins.2010.08.041 Kobozev, 1966, Physicochemical modelling of information and thinking processes. I. Thermodynamics of the information processes, Russ. J. Phys. Chem. A, 40, 281 Terentyeva, 1976, On possible relations between entropy of information theory and thermodynamic entropy, Russ. J. Phys. Chem. A, 50, 877 Aleskovskii, 2002, Information as a factor of self-organization and organization of matter, Russ. J. Gen. Chem., 72, 569, 10.1023/A:1016392432568 Talanov, 2013, Structure as the source of information on the chemical organization of substance, Russ. J. Gen. Chem., 83, 2225, 10.1134/S1070363213120013 Sabirov, 2015, Information entropy of fullerenes, J. Chem. Inf. Model., 55, 1576, 10.1021/acs.jcim.5b00334 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 Ōsawa, 2012, Formation mechanism of C60 under nonequilibrium and irreversible conditions — an annotation, Fullerene Nanotube Carbon Nanostruct., 20, 299, 10.1080/1536383X.2012.655104 Sabirov, 2015, Information entropy of oxygen allotropes. A still open discussion about the closed form of ozone, Comput. Theor. Chem., 1073, 61, 10.1016/j.comptc.2015.09.016 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 Sabirov, 2018, Information entropy changes in chemical reactions, Comput. Theor. Chem., 1123, 169, 10.1016/j.comptc.2017.11.022 Ugi, 1971, Representation of chemical systems and interconversions bybe matrices and their transformation properties, Angew. Chem. Int. Ed. Engl., 10, 914, 10.1002/anie.197109141 Stankevich, 1988, Topological indices in organic chemistry, Russ. Chem. Rev., 57, 191, 10.1070/RC1988v057n03ABEH003344 Sokolov, 1991 Chambadal, 1963