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Nitropyridine-1-Oxides as Excellent π-Hole Donors: Interplay between σ-Hole (Halogen, Hydrogen, Triel, and Coordination Bonds) and π-Hole Interactions
| Content Provider | Semantic Scholar |
|---|---|
| Author | Galmés, Bartomeu Franconetti, Antonio Frontera, Antonio |
| Copyright Year | 2019 |
| Abstract | In this manuscript, we use the primary source of geometrical information, i.e., Cambridge Structural Database (CSD), combined with density functional theory (DFT) calculations (PBE0-D3/def2-TZVP level of theory) to demonstrate the relevance of π-hole interactions in para-nitro substituted pyridine-1-oxides. More importantly, we show that the molecular electrostatic potential (MEP) value above and below the π-hole of the nitro group is largely influenced by the participation of the N-oxide group in several interactions like hydrogen-bonding (HB) halogen-bonding (XB), triel bonding (TrB), and finally, coordination-bonding (CB) (N+-O- coordinated to a transition metal). The CSD search discloses that p-nitro-pyridine-1-oxide derivatives have a strong propensity to participate in π-hole interactions via the nitro group and, concurrently, N-oxide group participates in a series of interactions as electron donor. Remarkably, the DFT calculations show from strong to moderate cooperativity effects between π-hole and HB/XB/TrB/CB interactions (σ-bonding). The synergistic effects between π-hole and σ-hole bonding interactions are studied in terms of cooperativity energies, using MEP surface analysis and the Bader's quantum theory of atoms in molecules (QTAIM). |
| File Format | PDF HTM / HTML |
| DOI | 10.3390/ijms20143440 |
| PubMed reference number | 31336936 |
| Journal | Medline |
| Volume Number | 20 |
| Alternate Webpage(s) | https://res.mdpi.com/d_attachment/ijms/ijms-20-03440/article_deploy/ijms-20-03440-v2.pdf |
| Alternate Webpage(s) | https://doi.org/10.3390/ijms20143440 |
| Journal | International journal of molecular sciences |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
