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A topological assessment of the electronic structure of mesoionic compounds
Author(s) -
Anjos Italo Curvelo,
Rocha Gerd Bruno
Publication year - 2015
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.24027
Subject(s) - mesoionic , electronic structure , topology (electrical circuits) , computational chemistry , computer science , chemistry , mathematics , combinatorics , organic chemistry
Mesoionic compounds belonging to the 1,3‐oxazol‐5‐one, 1,3‐diazole‐4‐thione and 1,3‐thiazole‐5‐thione rings have been evaluated by a combination of Density Functional Theory, Quantum Theory of Atoms in Molecules, Electron Localization Function, Natural Bond Orbitals and Geodesic Electrostatic Potential Charge calculations. Atomic, bond, and ring properties have been considered to describe the electronic structure of mesoionic compounds. The results show that not only the ring type, but also the substituent groups have great influence on these properties. In addition, there is a significant and heterogeneous π‐bonding contribution throughout the mesoionic rings. Finally, we conclude that some classical conceptions of charge localization and π‐bonding contribution in these compounds are misleading or incomplete. © 2015 Wiley Periodicals, Inc.