Name
Abstract | ||
|---|---|---|
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 pi-electron delocalization in the six-membered ring. The resulting H-bonded 4-pyridone units display enhanced pi-aromatic character (both magnetically and energetically) and their corresponding N-H center dot center dot center dot O=C interactions are strengthened. These p-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. (C) 2015 Wiley Periodicals, Inc. |
Year | DOI | Venue |
|---|---|---|
2016 | 10.1002/jcc.23976 | JOURNAL OF COMPUTATIONAL CHEMISTRY |
Keywords | DocType | Volume |
self-assembly, hydrogen bonding, aromaticity, nucleus independent chemical shifts, energy decomposition analysis | Journal | 37 |
Issue | ISSN | Citations |
1 | 0192-8651 | 0 |
PageRank | References | Authors |
0.34 | 0 | 4 |
Name | Order | Citations | PageRank |
|---|---|---|---|
| Megha Anand | 1 | 0 | 0.34 |
| Israel Fernández | 2 | 5 | 2.32 |
| Henry F Schaefer | 3 | 22 | 7.18 |
| Judy I.-Chia Wu | 4 | 0 | 0.34 |