Parallel Interactions at Large Horizontal Displacement in Pyridine–Pyridine and Benzene–Pyridine Dimers

Ninković, Dragan B.; Andrić, Jelena M.; Zarić, Snežana D.

doi:10.1002/cphc.201200607

Cited by 48 publications

(51 citation statements)

References 48 publications

Supporting

Mentioning

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

“…The data in Figure 3 show that most of the parallel contacts have the normal distances between 3.0 and 3.5 Å. These are distances typical for stacking of organic aromatic rings (3-4 Å) [17][18][19][20][21][22] and other planar rings that form stacking interactions [24][25][26][27][43][44][45][46]. The data in Figure 3 show that most of the parallel contacts have the normal distances between 3.0 and 3.5 Å.…”

Section: Search and Analysis Of Crystal Structures From The Csdmentioning

confidence: 95%

Very Strong Parallel Interactions Between Two Saturated Acyclic Groups Closed with Intramolecular Hydrogen Bonds Forming Hydrogen-Bridged Rings

2016

View full text Add to dashboard Cite

Saturated acyclic four-atom groups closed with a classic intramolecular hydrogen bond, generating planar five-membered rings (hydrogen-bridged quasi-rings), in which at least one of the ring atoms is bonded to other non-ring atoms that are not in the ring plane and, thus, capable to form intermolecular interactions, were studied in this work, in order to find the preferred mutual positions of these species in crystals and evaluate strength of intermolecular interactions. We studied parallel interactions of these rings by analysing crystal structures in the Cambridge Structural Database (CSD) and by quantum chemical calculations. The rings can have one hydrogen atom out of the ring plane that can form hydrogen bonds between two parallel rings. Hence, in these systems with parallel rings, two types of hydrogen bonds can be present, one in the ring, and the other one between two parallel rings. The CSD search showed that 27% of the rings in the crystal structures form parallel interactions. The calculations at very accurate CCSD(T)/CBS level revealed strong interactions, in model systems of thiosemicarbazide, semicarbazide and glycolamide dimers the energies are´9.68,´7.12 and 4.25 kcal/mol. The hydrogen bonds between rings, as well as dispersion interactions contribute to the strong interaction energies.

show abstract

“…Stacking interactions of two pyridines are, however, somewhat stronger than CH/π interactions (interaction energies are −3.80 and −3.56 kcal/mol, respectively) [58]. Recently, study on pyridine-pyridine interactions at large horizontal displacement was performed [23], and it will be discussed in this section.…”

Section: Heteroaromatic/heteroaromatic Interactions At Large Horizontmentioning

confidence: 99%

“…Parallel pyridine-pyridine interactions were studied by performing the CSD search on November 2011 release (version 5.33) [23]. Similar parameters to those for benzenebenzene parallel interactions were set ( Fig.…”

Section: Cambridge Structural Database Search For Pyridine-pyridine Imentioning

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