Controlling the molecular arrangement of racemates through weak interactions: the synergy between π-interactions and halogen bonds

2021 ◽  
Author(s):  
Carlos Romero-Nieto ◽  
A. de Cózar ◽  
Elzbieta Regulska ◽  
John B. Mullenix ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Weak Interactions ◽  
Halogen Bonds ◽  
Π Interactions ◽  
Molecular Arrangement ◽  
Π Stacking

The combination of halogend bonds from PO and N-moieties with π-stacking leads to sort out R- and S-isomers into homoleptic, porous assemblies.

scholarly journals Weak interactions in the crystal structures of two indole derivatives

2016 ◽  
Vol 72 (7) ◽  
pp. 964-968
Author(s):  
Jamie R. Kerr ◽  
Laurent Trembleau ◽  
John M. D. Storey ◽  
James L. Wardell ◽  
William T. A. Harrison
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Weak Interactions ◽  
Indole Derivatives ◽  
Halogen Bonds ◽  
Π Interactions ◽  
Π Stacking

We describe the syntheses and crystal structures of two indole derivatives, namely a second monoclinic polymorph of ethyl 5-chloro-1H-indole-2-carboxylate C11H10ClNO2, (I), and ethyl 5-chloro-3-iodo-1H-indole-2-carboxylate, C11H9ClINO2, (II). In their crystal structures, both compounds form inversion dimers linked by pairs of N—H...O hydrogen bonds, which generateR22(10) loops. The dimers are linked into double chains in (I) and sheets in (II) by a variety of weak interactions, including π–π stacking, C—I...π, C—Cl—π interactions and I...Cl halogen bonds.

Assisted π-stacking: a strong synergy between weak interactions

2018 ◽  
Vol 54 (86) ◽  
pp. 12186-12189 ◽  
Author(s):  
Soumik Sao ◽  
Sumit Naskar ◽  
Narottam Mukhopadhyay ◽  
Mousumi Das ◽  
Debangshu Chaudhuri
Keyword(s):  
Weak Interactions ◽  
Π Stacking

An exceptionally strong synergy between aromatic π-stacking and n → π* interaction.

Intermolecular π/π and H/π interactions in dimers researched by different computational methods

2014 ◽  
Vol 13 (07) ◽  
pp. 1450057
Author(s):  
Cuihong Wang ◽  
Yue Jiang ◽  
Ruiqin Zhang ◽  
Zijing Lin
Keyword(s):  
High Efficiency ◽  
Dipole Moments ◽  
Binding Energies ◽  
Basis Set ◽  
Theoretical Research ◽  
Basis Sets ◽  
Π Interactions ◽  
Π Stacking ◽  
Structures And Properties ◽  
Satisfactory Precision

The analysis of π/π and H /π interactions in complexes are a challenging aspect of theoretical research. Due to the different approximations of different levels of theory, results tend to be inconsistent. We compared the reliabilities of HF, SVWN, M06L, PW91, BLYP, B3LYP, BHandHLYP, B97D, MP2, and DFTB-D approaches in researching π/π and H /π interactions by calculating the binding energies of five benzene-containing dimers. The effects of 6-31+G**, 6-311++G** and 6-311++G(2df,2p) basis sets on the results were analyzed too. We found that the DFTB-D and B97D methods combined with the 6-311++G** basis set perform well for dimers that contain π/π and H /π interactions. With high efficiency and satisfactory precision, DFTB-D is helpful for the calculation of complexes containing π/π and H /π stacking. We further calculated the structures and properties of phenylalanine-containing dimers using the DFTB-D and B97D methods. The properties of low energy conformers such as rotational constants, dipole moments and molecular orbitals were also analyzed. These data should be helpful for research into systems that contain π/π and H /π stacking.

scholarly journals 6,8-Diiodo-4-oxo-4H-chromene-3-carbaldehyde

2014 ◽  
Vol 70 (5) ◽  
pp. o536-o536
Author(s):  
Yoshinobu Ishikawa
Keyword(s):  
Least Squares ◽  
Title Compound ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Halogen Bonds ◽  
Compound C ◽  
Π Stacking ◽  
Dimensional Network ◽  
Centroid Distance

The title compound, C10H4I2O3, is an iodinated 3-formylchromone derivative, and the atoms are essentially coplanar [r.m.s. deviation = 0.049 Å, largest deviation from the least-squares plane = 0.111 (9) Å for the CH(=O) C atom]. In the crystal, molecules are linked into a three-dimensional network through halogen bonds [I...O = 3.352 (5) and 3.405 (7) Å, C—I...O = 144.2 (3) and 154.5 (3)°, and C=O...I = 134.9 (6) and 146.0 (6)°], and π–π stacking interactions [centroid–centroid distance = 3.527 (6) Å].

Self-assembly of a Novel Three-dimensional Silver(I) Supramolecular Framework from Cationic Chains and Anionic Sheets

2010 ◽  
Vol 65 (2) ◽  
pp. 152-156
Author(s):  
Di Sun ◽  
Cheng-Feng Yang ◽  
Zhan-Hua Wei ◽  
Geng-Geng Luo ◽  
Na Zhang ◽  
...  
Keyword(s):  
Thermal Properties ◽  
Hydrogen Bonds ◽  
Self Assembly ◽  
Room Temperature ◽  
Three Dimensional ◽  
Supramolecular Framework ◽  
Π Interactions ◽  
Π Stacking ◽  
Benzenedicarboxylic Acid

A new three-dimensional (3D) supramolecular framework, [Ag2(bipy)2(bdc)·4H2O]n 1, has been synthesized by the ultrasonic reaction of Ag2O, bipy and H2bdc (H2bdc = 1,4-benzenedicarboxylic acid; bipy = 4,4’-bipyridine) at room temperature. It exhibits a new 3D supramolecular framework which is built from cationic Ag-bipy chains and anionic bdc-H2O sheets through hydrogen bonds, π · · ·π stacking and C-H· · ·π interactions. Additionally, the photoluminescent and thermal properties of 1 were investigated.

scholarly journals Noncovalent Interactions between 1,3,5-Trifluoro-2,4,6-triiodobenzene and a Series of 1,10-Phenanthroline Derivatives: A Combined Theoretical and Experimental Study

Crystals ◽  
2019 ◽  
Vol 9 (3) ◽  
pp. 140 ◽  
Author(s):  
Yu Zhang ◽  
Jian-Ge Wang ◽  
Weizhou Wang
Keyword(s):  
Crystal Structure ◽  
Crystal Structures ◽  
Quantum Chemical ◽  
Halogen Bond ◽  
Noncovalent Interactions ◽  
Stacking Interactions ◽  
Halogen Bonds ◽  
Π Stacking ◽  
Π Stacking Interaction ◽  
Structural Competition

How many strong C−I⋯N halogen bonds can one 1,3,5-trifluoro-2,4,6-triiodobenzene molecule form in a crystal structure? To answer this question, we investigated in detail the noncovalent interactions between 1,3,5-trifluoro-2,4,6-triiodobenzene and a series of 1,10-phenanthroline derivatives by employing a combined theoretical and experimental method. The results of the quantum chemical calculations and crystallographic experiments clearly show that there is a structural competition between a C−I⋯N halogen bond and π⋯π stacking interaction. For example, when there are much stronger π⋯π stacking interactions between two 1,10-phenanthroline derivative molecules or between two 1,3,5-trifluoro-2,4,6-triiodobenzene molecules in the crystal structures, then one 1,3,5-trifluoro-2,4,6-triiodobenzene molecule forms only one C−I⋯N halogen bond with one 1,10-phenanthroline derivative molecule. Another example is when π⋯π stacking interactions in the crystal structures are not much stronger, one 1,3,5-trifluoro-2,4,6-triiodobenzene molecule can form two C−I⋯N halogen bonds with two 1,10-phenanthroline derivative molecules.

Synthetic Ion Transporters that Work with Anion−π Interactions, Halogen Bonds, and Anion–Macrodipole Interactions

2013 ◽  
Vol 46 (12) ◽  
pp. 2791-2800 ◽  
Author(s):  
Andreas Vargas Jentzsch ◽  
Andreas Hennig ◽  
Jiri Mareda ◽  
Stefan Matile
Keyword(s):  
Ion Transporters ◽  
Halogen Bonds ◽  
Π Interactions

[(Z)-2-(3-Methyl-1,2,4-oxadiazol-5-yl)-2-(1-naphthyl)ethenylamino]formaldehyde oxime 1,4-dioxane hemisolvate

2007 ◽  
Vol 63 (11) ◽  
pp. o4261-o4262
Author(s):  
Kensuke Okuda ◽  
Hiromi Watanabe ◽  
Takashi Hirota ◽  
Kazuma Gotoh ◽  
Hiroyuki Ishida
Keyword(s):  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Title Compound ◽  
Solvent Molecule ◽  
Asymmetric Unit ◽  
Π Interactions ◽  
Compound C ◽  
Π Stacking ◽  
Centroid Distance ◽  
Independent Molecules

In the asymmetric unit of the title compound, C16H14N4O2·0.5C4H8O2, there are two crystallographically independent oxime molecules and one solvent molecule. Each oxime molecule has intramolecular N—H...O and N—H...N hydrogen bonds, which make the non-H atoms approximately coplanar except for the naphthyl groups. The two independent molecules are connected to each other by O—H...N hydrogen bonds, forming a dimer. Dimers are linked into a layer through C—H...O, C—H...N and C—H...π interactions. There is π-stacking of approximately parallel oxadiazole rings, with a centroid–centroid distance of 3.6234 (9) Å and a dihedral angle of 8.90 (6)°. Dioxane C and H atoms are disordered over two sites each, with occupancy factors of ca 0.78:0.22.

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