Anion-π interactions

Schottel, Brandi L.; Chifotides, Helen T.; Dunbar, Kim R.

doi:10.1039/b614208g

Cited by 1,056 publications

(727 citation statements)

References 58 publications

(136 reference statements)

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“…Hydrogen bonds (HBs) are by far the most frequently occurring and widely studied type of interaction [4,5]; other weak interactions that have traditionally received attention include π-π [6], cation-π [7], anion-π [8], and aurophilic [9] bonds. σ-Hole interactions [10][11][12] represent a relatively recent entry into the canon of weak bonds [13][14][15], but following the seminal papers of P. Politzer et al [16,17], these interactions rapidly became popular targets for studies in this field [15,[18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

et al. 2018

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Modeling indicates the presence of a region of low electronic density (a Bσ-hole^) on group 14 elements, and this offers an explanation for the ability of these elements to act as electrophilic sites and to form attractive interactions with nucleophiles. While many papers have described theoretical investigations of interactions involving carbon and silicon, such investigations of the heavier group 14 elements are relatively scarce. The purpose of this review is to rectify, to some extent, the current lack of experimental data on interactions formed by germanium and tin with nucleophiles. A survey of crystal structures in the Cambridge Structural Database is reported. This survey reveals that close contacts between Ge or Sn and lone-pair-possessing atoms are quite common, they can be either intra-or intermolecular contacts, and they are usually oriented along the extension of the covalent bond formed by the tetrel with the most electron-withdrawing substituent. Several examples are discussed in which germanium and tin atoms bear four carbon residues or in which halogen, oxygen, sulfur, or nitrogen substituents replace one, two, or three of those carbon residues. These close contacts are assumed to be the result of attractive interactions between the involved atoms and afford experimental evidence of the ability of germanium and tin to act as electrophilic sites, namely tetrel bond (TB) donors. This ability can govern the conformations and the packing of organic derivatives in the solid state. TBs can therefore be considered a promising and robust tool for crystal engineering.

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Section: Introductionmentioning

confidence: 99%

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

et al. 2018

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“…They play a key role in supramolecular chemistry which is defined as ''chemistry beyond the molecule'' and are without doubt the dominant type of interaction in maintaining the three-dimensional structure of large systems such as proteins, nucleic acids and other large molecules [1][2][3][4][5][6][7][8]. In these systems, NCI involving aromatic rings can be distinguished and those are for instance: p-stacking, cation/p, anion-p, C-H/p and N-H/p interactions [9][10][11][12][13][14]. The understanding of their nature together with their interplaying and dependencies between different types of NCI (for instance p-stacking vs N-H/p) is critical for harnessing their full potential in chemistry, especially when the precise control of the strength and geometry of intermolecular interactions is concerned, e.g.…”

Section: Introductionmentioning

confidence: 99%

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

Sierański

2016

Struct Chem

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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.

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“…−5°and 42°for methyl C20 and methyl C21 respectively. The packing is governed by strong anion⋯π interactions 13 between the fluorine atom of the PF 6 − ion and the imide ring (F3⋯centroid distance 2.875 Å) and π⋯π stacking interactions between the naphthalene rings on adjacent molecules (centroid⋯centroid distance 3.521 Å) resulting in head-to-tail organisations of the naphthalimide molecules. In addition there is a very weak anion⋯π interaction between the pyridinium ring and the PF 6 − (F2⋯centroid = 3.628 Å) giving an overall π⋯anion⋯π interaction (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…All NMR spectra were recorded using either a Bruker DPX-400 or AV-600 spectrometer, operating at 400/600 MHz for 1 H NMR and 100/150 MHz for 13 C NMR, respectively. Chemical shifts were referenced relative to the internal solvent signals.…”

Section: General Experimental Detailsmentioning

confidence: 99%

The effect of the 4-amino functionality on the photophysical and DNA binding properties of alkyl-pyridinium derived 1,8-naphthalimides

et al. 2013

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The synthesis and characterisation of two cationic pyridinium based 4-amino-1,8-naphthalimide derivatives (2 and 3) are described and compared to those of compound 1. The photophysical properties of 2 and 3 are shown to vary greatly with the solvent polarity and H-bonding ability. The dimethylamino substitution in 3 results in a weak quantum yield of fluorescence emission due to faster non-radiative deactivation of the excited singlet state than that seen for 2. As with 1, the fluorescence of 2 was found to be enhanced in its 1 : 1 complex with 5'-adenosine-monophosphate (5'-AMP) while it was partially quenched in its complex with 5'-guanosine-monophosphate (5'-GMP). In contrast, the fluorescence of 3 was enhanced ('switched on') in the presence of both adenine and guanine rich sequences. Linear and circular dichroism studies showed that each of 1, 2 and 3 binds to double-stranded DNA by intercalation. However, 2 and 3 do not show the preference for AT-rich DNA observed for 1. Comparative fluorescence studies with double stranded DNA show that the emission of 3 was 16 times enhanced in its DNA bound form, suggesting potential use of this structure as a spectroscopic probe for studying nucleic acid structure.

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Anion-π interactions

Cited by 1,056 publications

References 58 publications

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

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

The effect of the 4-amino functionality on the photophysical and DNA binding properties of alkyl-pyridinium derived 1,8-naphthalimides

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