What Are the Preferred Horizontal Displacements in Parallel Aromatic–Aromatic Interactions? Significant Interactions at Large Displacements

Ninković, Dragan B.; Janjić, Goran V.; Veljković, Dušan Ž.; Sredojević, Dušan N.; Zarić, Snežana D.

doi:10.1002/cphc.201100777

Cited by 80 publications

(124 citation statements)

References 32 publications

Supporting

Mentioning

110

Contrasting

Order By: Relevance

“…However, the bonding geometry boundaries are relatively broad, and the stacking interactions can be binding even for ring centroid distances larger than 6 Å , provided that the stacked rings are in an appropriate geometry. Recently, the same has been observed for sixmembered aromatic ring systems [81][82][83].…”

Section: Resultssupporting

confidence: 73%

The intricacies of the stacking interaction in a pyrrole–pyrrole system

Sierański

2016

Struct Chem

View full text Add to dashboard Cite

Extensive calculations of potential energy surfaces for parallel-displaced configurations of pyrrole-pyrrole systems have been carried out by the use of a dispersion-corrected density functional. System geometries associated with the energy minima have been found. The minimum interaction energy has been calculated as -5.38 kcal/mol. However, bonding boundaries appeared to be relatively broad, and stacking interactions can be binding even for ring centroid distances larger than 6 Å . Though the contribution of the correlation energy to intermolecular interaction in pyrrole dimers appeared to be relatively small (around 1.6 smaller than it is in a benzenebenzene system), this system's minimum interaction energy is lower than those calculated for benzene-benzene, benzene-pyridine and even pyridine-pyridine configurations. The calculation of the charges and energy decomposition analysis revealed that the specific charge distribution in a pyrrole molecule and its relatively high polarization are the significant source of the intermolecular interaction in pyrrole dimer systems.

show abstract

Section: Resultssupporting

confidence: 73%

The intricacies of the stacking interaction in a pyrrole–pyrrole system

Sierański

2016

Struct Chem

View full text Add to dashboard Cite

show abstract

“…14.25) are similar to interactions between two parallel benzene molecules [24]. At horizontal displacements of 3.5 and 4.5 Å, interaction energies for interplanar angles of 20° and 40° are substantial (from −2.01 to −2.13 kcal/mol, Table 14.7), which is more than 70% of the strongest interaction energy, as it was previously determined for parallel benzene-benzene contacts [22]. At horizontal displacements of 3.5 and 4.5 Å, interaction energies for interplanar angles of 20° and 40° are substantial (from −2.01 to −2.13 kcal/mol, Table 14.7), which is more than 70% of the strongest interaction energy, as it was previously determined for parallel benzene-benzene contacts [22].…”

Section: Dft Calculations Of Interaction Energies Of Aromatic-aromatisupporting

confidence: 73%

“…The CSD November 2010 release (version 5.32) was subjected to search for parallel benzene-benzene contacts [22]. It was considered that two benzene molecules form parallel interaction if the angle between their mean planes is less than 10°, the distance d between their centers is less than 6.0 Å, and normal distance between their planes is less than 4.0 Å (Fig.…”

Section: Cambridge Structural Database Search Of Parallel Benzene/benmentioning

confidence: 99%

“…It should be noted that, relative to benzene ring center, carbon atoms are at horizontal displacement of approximately 1.4 Å and hydrogen atoms at horizontal displacement of approximately 2.5 Å (Fig. During the last few years, several studies were published that showed that substantial parallel interactions are formed at large horizontal displacements [17][18][19][20][21][22][23][24]. Interacting molecules can be considered at large horizontal displacement relative to benzene if all of its atoms are out of the ring plane and beyond the C─H bond region, that is, with r > 2.5 Å.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Parallel Interactions of Aromatic Molecules at Large Horizontal Displacements

Malenov

Zarić

2016

Non‐covalent Interactions in the Synthesis and Design of New Compounds

Self Cite

View full text Add to dashboard Cite

“…Chelate rings with a delocalized π-system can form CH/π [38][39][40][41][42][43][44] and stacking interactions [45][46][47][48][49] in a similar way to organic aromatic rings [50][51][52][53][54][55][56][57][58]. In our previous studies, structural and computational evidence has been given for a particular type of CH/π interaction where the hydrogen atom interacts with various chelate rings [38][39][40][41].…”

Section: Introductionmentioning

confidence: 99%