Stacking interaction between homostacks of simple aromatics and the factors influencing these interactions

Choudhury, Rajul Ranjan; Читра, Р.

doi:10.1039/b919793a

Cited by 37 publications

(31 citation statements)

References 11 publications

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“…The preference for the head-to-tail orientation in crystal structures is in good accordance with previous highly accurate quantumchemical calculations (Mishra & Sathyamurthy, 2005;Mishra et al, 2010). Recent studies have shown that the hydrogen-bonding capacity of the N atom is related to the strength of the stacking interaction between the rings (Mignon et al, 2004(Mignon et al, , 2005Ebrahimi et al, 2009;Choudhury & Chitra, 2010). Our previous results also indicate the large influence of hydrogen bonding, as shown in Fig.…”

Section: Resultssupporting

confidence: 91%

Influence of supramolecular structures in crystals on parallel stacking interactions between pyridine molecules

Janjić

Ninković

Zarić

2013

Acta Crystallogr Sect B

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Parallel stacking interactions between pyridines in crystal structures and the influence of hydrogen bonding and supramolecular structures in crystals on the geometries of interactions were studied by analyzing data from the Cambridge Structural Database (CSD). In the CSD 66 contacts of pyridines have a parallel orientation of molecules and most of these pyridines simultaneously form hydrogen bonds (44 contacts). The geometries of stacked pyridines observed in crystal structures were compared with the geometries obtained by calculations and explained by supramolecular structures in crystals. The results show that the mean perpendicular distance (R) between pyridine rings with (3.48 Å) and without hydrogen bonds (3.62 Å) is larger than that calculated, because of the influence of supramolecular structures in crystals. The pyridines with hydrogen bonds show a pronounced preference for offsets of 1.25-1.75 Å, close to the position of the calculated minimum (1.80 Å). However, stacking interactions of pyridines without hydrogen bonds do not adopt values at or close to that of the calculated offset. This is because stacking interactions of pyridines without hydrogen bonds are less strong, and they are more susceptible to the influence of supramolecular structures in crystals. These results show that hydrogen bonding and supramolecular structures have an important influence on the geometries of stacked pyridines in crystals.

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Section: Resultssupporting

confidence: 91%

Influence of supramolecular structures in crystals on parallel stacking interactions between pyridine molecules

Janjić

Ninković

Zarić

2013

Acta Crystallogr Sect B

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“…Substitution of heteroatoms in Pyr and PY strengthens the π‐stacking interaction energy compared to Bz 2 and increases the likelihood that small aromatics will form stacks in bulk crystalline phases . The DFT(M06‐2X)/aug‐cc‐pVTZ interaction energies in various orientations of Pyr 2 (Figure A) agree with results reported by Hohenstein and Sherrill (Table ) .…”

Section: Resultssupporting

confidence: 85%

Interpreting geometric preferences in π‐stacking interactions through molecular orbital analysis

Lutz

Bayse

2017

Int J of Quantum Chemistry

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The preference of π‐stacking interactions for parallel‐displaced (PD) and twisted (TW) conformations over the fully eclipsed sandwich (S) in small π‐stacked dimers of benzene, pyridine, pyrimidine, 1,3,5‐trifluorobenzene, and hexafluorobenzene are examined in terms of enhancement of the inter‐ring density through mixing of the monomer orbitals (MOs). PD and/or TW conformations are consistent with a non‐zero “stack bond order” (SBO), defined in analogy to the bond order of conventional MO theory, as the difference in the occupation of bonding and antibonding π‐type dimer MOs. In the S conformation, the equal number of bonding and antibonding MOs cancel overall stack bonding character between the monomers for an SBO of zero and an overall repulsive interaction. PD from the S shifts the character of at least one antibonding combination of monomer π‐type MOs with nodes perpendicular to the coordinate for PD to bonding, leading to an attractive nonzero SBO. The inter‐ring density measured through the Wiberg bond index analysis shows an enhancement at the PD conformations consistent with greater interpenetration of the monomer densities. This intuitive bonding model for π‐stacking interactions is complementary to highly accurate calculations of π‐stacking energies and allows a predictive understanding of relative stability using cheaper quantum chemical methods.

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“…The interplanar separation of adjacent chelate rings is even somewhat shorter than the graphite spacing of 3.35 Å [67]. The centroid-centroid and Cu1ÁÁÁC8 distances found in 1 are among the shortest found in Cu(b-diketonato) 2 compounds and p-p interactions are consistent with well-defined p-p stacking interactions [68][69][70][71]. As classified by Janiak et al [72][73][74], interactions in nitrogen-containing heteroaromatic compounds are regarded as strong interactions, when rather short centroid-centroid contacts (CgÁÁÁCg \ 3.8 Å ), small slip angles (\25°) and small vertical displacements (\1.5 Å ) translate into a sizeable overlap of the aromatic planes.…”

Section: Crystal Aggregation Ofsupporting

confidence: 59%

Different coordination modes and supramolecular aggregations in copper(II) pentane-2,4-dionato compounds with 2-pyridone and 3-hydroxypyridine

Perdih

2012

Monatsh Chem

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Copper(II) bis(pentane-2,4-dionato-j 2 O,O 0 ) compounds with 2-pyridone (1) and 3-hydroxypyridine (2) were prepared by the reaction of bis(pentane-2,4-dionato-j 2 O,O 0 ) copper(II) with selected ligands. The coordination of Cu(II) in both compounds is square pyramidal with the fifth coordination site occupied by the carbonyl oxygen atom of the 2-pyridone ligand in 1 and by the nitrogen atom of 3-hydroxypyridine in 2. The X-ray crystallographic studies revealed different crystal aggregation influenced by the ability of the 2-pyridone ligand to act as a hydrogen bond donor and acceptor, and 3-hydroxypyridine acting only as a hydrogen bond donor. Intermolecular N-HÁÁÁO hydrogen bonding forms dimers in 1 and infinite chains in 2. Three-dimensional aggregation is achieved by p-p interactions and C-HÁÁÁp (arene) hydrogen bonding.

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Stacking interaction between homostacks of simple aromatics and the factors influencing these interactions

Cited by 37 publications

References 11 publications

Influence of supramolecular structures in crystals on parallel stacking interactions between pyridine molecules

Influence of supramolecular structures in crystals on parallel stacking interactions between pyridine molecules

Interpreting geometric preferences in π‐stacking interactions through molecular orbital analysis

Different coordination modes and supramolecular aggregations in copper(II) pentane-2,4-dionato compounds with 2-pyridone and 3-hydroxypyridine

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