Hydrogen bond-aromaticity cooperativity in self-assembling 4-pyridone chains
© 2015 Wiley Periodicals, Inc.
| Veröffentlicht in: | Journal of computational chemistry. - 1984. - 37(2016), 1 vom: 05. Jan., Seite 59-63 |
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| Weitere Verfasser: | , , |
| Format: | Online-Aufsatz |
| Sprache: | English |
| Veröffentlicht: |
2016
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| Zugriff auf das übergeordnete Werk: | Journal of computational chemistry |
| Schlagworte: | Journal Article aromaticity energy decomposition analysis hydrogen bonding nucleus independent chemical shifts self-assembly |
| Zusammenfassung: | © 2015 Wiley Periodicals, Inc. Self-assembling building blocks like the 4-pyridone can exhibit extraordinary H-bond-aromaticity coupling effects. Computed dissected nucleus independent chemical shifts (NICS(1)zz), natural bond orbital (NBO) charges, and energy decomposition analyses (EDA) for a series of hydrogen (H-) bonded 4-pyridone chains (4-py)n (n = 2 to 8) reveal that H-bonding interactions can polarize the 4-pyridone exocyclic C=O bonds and increase 4n+2 π-electron delocalization in the six-membered ring. The resulting H-bonded 4-pyridone units display enhanced π-aromatic character (both magnetically and energetically) and their corresponding N-H···O=C interactions are strengthened. These π-electron polarization effects do not depend on the relative orientations (co-planar or perpendicular) of the neighboring 4-pyridone units, but increase with the number of H-bonded units |
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| Beschreibung: | Date Completed 23.03.2016 Date Revised 07.12.2015 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
| ISSN: | 1096-987X |
| DOI: | 10.1002/jcc.23976 |