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Magnetic Shielding, Aromaticity, Antiaromaticity and Bonding in the Low-Lying Electronic States of Benzene and Cyclobutadiene

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JournalJournal of Organic Chemistry
DateAccepted/In press - 27 Oct 2016
DateE-pub ahead of print - 27 Oct 2016
DatePublished (current) - 18 Nov 2016
Issue number22
Number of pages7
Pages (from-to)11346-11352
Early online date27/10/16
Original languageEnglish


Aromaticity, antiaromaticity, and their effects on chemical bonding in the ground states (S 0), lowest triplet states (T 1), and the first and second singlet excited states (S 1 and S 2) of benzene (C 6H 6) and square cyclobutadiene (C 4H 4) are investigated by analyzing the variations in isotropic magnetic shielding around these molecules in each electronic state. All shieldings are calculated using state-optimized π-space complete-active-space self-consistent field (CASSCF) wave functions constructed from gauge-including atomic orbitals (GIAOs), in the 6-311++G(2d,2p) basis. It is shown that the profoundly different shielding distributions in the S 0 states of C 6H 6 and C 4H 4 represent aromaticity and antiaromaticity "fingerprints" which are reproduced in other electronic states of the two molecules and allow classification of these states as aromatic (S 0 and S 2 for C 6H 6, T 1 and S 1 for C 4H 4) or antiaromatic (S 0 and S 2 for C 4H 4, T 1 and S 1 for C 6H 6). S 2 C 6H 6 is predicted to be even more aromatic than S 0 C 6H 6. As isotropic shielding isosurfaces and contour plots show very clearly the effects of aromaticity and antiaromaticity on chemical bonding, these can be viewed, arguably, as the most succinct visual definitions of the two phenomena currently available.

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© 2016, American Chemical Society. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

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