scholarly journals Inclusion complexes of Cethyl-2-methylresorcinarene and pyridine N-oxides: breaking the C–I⋯−O–N+ halogen bond by host–guest complexation

CrystEngComm ◽  
2016 ◽  
Vol 18 (5) ◽  
pp. 793-799 ◽  
Author(s):  
Rakesh Puttreddy ◽  
Ngong Kodiah Beyeh ◽  
Kari Rissanen
Keyword(s):  
Inclusion Complexes ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Π Interactions ◽  
Guest Chemistry

Cethyl-2-Methylresorcinarene and aromatic N-oxides manifest host–guest chemistry by C–H⋯π interactions and halogen bonding; the C–I⋯−O–N+ halogen bond with 2-iodopyridine N-oxide is broken by the in-cavity C–I⋯π interactions.

scholarly journals The Effect of Pressure on Halogen Bonding in 4-Iodobenzonitrile

Molecules ◽  
2019 ◽  
Vol 24 (10) ◽  
pp. 2018 ◽  
Author(s):  
Nico Giordano ◽  
Sergejs Afanasjevs ◽  
Christine M. Beavers ◽  
Claire L. Hobday ◽  
Konstantin V. Kamenev ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Halogen Bond ◽  
Ambient Pressure ◽  
Halogen Bonding ◽  
Optical Transmittance ◽  
Monoclinic Space Group ◽  
Ambient Conditions ◽  
Π Interactions ◽  
Transparent Crystal ◽  
Triclinic Phase

The crystal structure of 4-iodobenzonitrile, which is monoclinic (space group I2/a) under ambient conditions, contains chains of molecules linked through C≡N···I halogen-bonds. The chains interact through CH···I, CH···N and π-stacking contacts. The crystal structure remains in the same phase up to 5.0 GPa, the b axis compressing by 3.3%, and the a and c axes by 12.3 and 10.9 %. Since the chains are exactly aligned with the crystallographic b axis these data characterise the compressibility of the I···N interaction relative to the inter-chain interactions, and indicate that the halogen bond is the most robust intermolecular interaction in the structure, shortening from 3.168(4) at ambient pressure to 2.840(1) Å at 5.0 GPa. The π∙∙∙π contacts are most sensitive to pressure, and in one case the perpendicular stacking distance shortens from 3.6420(8) to 3.139(4) Å. Packing energy calculations (PIXEL) indicate that the π∙∙∙π interactions have been distorted into a destabilising region of their potentials at 5.0 GPa. The structure undergoes a transition to a triclinic ( P 1 ¯ ) phase at 5.5 GPa. Over the course of the transition, the initially colourless and transparent crystal darkens on account of formation of microscopic cracks. The resistance drops by 10% and the optical transmittance drops by almost two orders of magnitude. The I···N bond increases in length to 2.928(10) Å and become less linear [<C−I∙∙∙N = 166.2(5)°]; the energy stabilises by 2.5 kJ mol−1 and the mixed C-I/I..N stretching frequency observed by Raman spectroscopy increases from 249 to 252 cm−1. The driving force of the transition is shown to be relief of strain built-up in the π∙∙∙π interactions rather than minimisation of the molar volume. The triclinic phase persists up to 8.1 GPa.

scholarly journals Halogen bonding and host–guest chemistry between N-alkylammonium resorcinarene halides, diiodoperfluorobutane and neutral guests

2019 ◽  
Vol 15 ◽  
pp. 947-954 ◽  
Author(s):  
Fangfang Pan ◽  
Mohadeseh Dashti ◽  
Michael R Reynolds ◽  
Kari Rissanen ◽  
John F Trant ◽  
...  
Keyword(s):  
Single Crystal ◽  
Crystal Lattice ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
X Ray ◽  
Bonded Complexes ◽  
Guest Chemistry

Single crystal X-ray structures of halogen-bonded assemblies formed between host N-hexylammonium resorcinarene bromide (1) or N-cyclohexylammonium resorcinarene chloride (2), and 1,4-diiodooctafluorobutane and accompanying small solvent guests (methanol, acetonitrile and water) are presented. The guests’ inclusion affects the geometry of the cavity of the receptors 1 and 2, while the divalent halogen bond donor 1,4-diiodooctafluorobutane determines the overall nature of the halogen bond assembly. The crystal lattice of 1 contains two structurally different dimeric assemblies A and B, formally resulting in the mixture of a capsular dimer and a dimeric pseudo-capsule. 1H and 19F NMR analyses supports the existence of these halogen-bonded complexes and enhanced guest inclusion in solution.

Modulating the assembly of N-benzylideneaniline by halogen bonding: crystal, cocrystal and liquid crystals

CrystEngComm ◽  
2017 ◽  
Vol 19 (27) ◽  
pp. 3801-3807 ◽  
Author(s):  
Yufei Wang ◽  
Hongxing Shang ◽  
Bao Li ◽  
Houyu Zhang ◽  
Shimei Jiang
Keyword(s):  
Liquid Crystals ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Π Interactions ◽  
Donor Acceptor

A halogen bond donor–acceptor N-benzylideneaniline self-assembles into an unusual head-to-head chain and a fishbone-like array by C–I⋯π and π⋯π interactions. Furthermore, it forms halogen-bonded cocrystal and liquid crystals with 4,4′-bipyridine or 4-alkoxystilbazole.

New deep cavitand with imidazoquinoxaline flaps: formation of static helical alkane inclusion complexes by enhanced CH/π interactions

2009 ◽  
pp. 4971 ◽  
Author(s):  
Heung-Jin Choi ◽  
Quoc-Thiet Nguyen ◽  
Yeon Sil Park ◽  
Cheol-Ho Choi ◽  
Kyungsoo Paek ◽  
...  
Keyword(s):  
Inclusion Complexes ◽  
Π Interactions

scholarly journals Adenine as a Halogen Bond Acceptor: A Combined Experimental and DFT Study

Crystals ◽  
2019 ◽  
Vol 9 (4) ◽  
pp. 224 ◽  
Author(s):  
Yannick Roselló ◽  
Mónica Benito ◽  
Elies Molins ◽  
Miquel Barceló-Oliver ◽  
Antonio Frontera
Keyword(s):  
Density Functional ◽  
Halogen Bond ◽  
Lone Pair ◽  
Halogen Bonding ◽  
Density Functional Theory Calculations ◽  
Functional Theory ◽  
Adenine Ring ◽  
Bonding Interaction ◽  
Donor Ability ◽  
Adenine Derivative

In this work, we report the cocrystallization of N9-ethyladenine with 1,2,4,5-tetrafluoro-3,6-diiodobenzene (TFDIB), a classical XB donor. As far as our knowledge extends, this is the first cocrystal reported to date where an adenine derivative acts as a halogen bond acceptor. In the solid state, each adenine ring forms two centrosymmetric H-bonded dimers: one using N1···HA6–N6 and the other N7···HB6–N6. Therefore, only N3 is available as a halogen bond acceptor that, indeed, establishes an N···I halogen bonding interaction with TFDIB. The H-bonded dimers and halogen bonds have been investigated via DFT (Density Functional Theory) calculations and the Bader’s Quantum Theory of Atoms In Molecules (QTAIM) method at the B3LYP/6-311+G* level of theory. The influence of H-bonding interactions on the lone pair donor ability of N3 has also been analyzed using the molecular electrostatic potential (MEP) surface calculations.

Cyclic networks of halogen-bonding interactions in molecular self-assemblies: a theoretical N—X...NversusC—X...N investigation

2017 ◽  
Vol 73 (2) ◽  
pp. 179-187
Author(s):  
Ruben D. Parra ◽  
Álvaro Castillo
Keyword(s):  
Electron Density ◽  
Self Assembly ◽  
Metal Ion ◽  
Halogen Atom ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Nbo Analysis ◽  
Binding Energies ◽  
Cyclic Network ◽  
Ability To Drive

The geometries and energetics of molecular self-assembly structures that contain a sequential network of cyclic halogen-bonding interactions are investigated theoretically. The strength of the halogen-bonding interactions is assessed by examining binding energies, electron charge transfer (NBO analysis) and electron density at halogen-bond critical points (AIM theory). Specifically, structural motifs having intramolecular N—X...N (X= Cl, Br, or I) interactions and the ability to drive molecular self-assemblyviathe same type of interactions are used to construct larger self-assemblies of up to three unit motifs. N—X...N halogen-bond cooperativity as a function of the self-assembly size, and the nature of the halogen atom is also examined. The cyclic network of the halogen-bonding interactions provides a suitable cavity rich in electron density (from the halogen atom lone pairs not involved in the halogen bonds) that can potentially bind an electron-deficient species such as a metal ion. This possibility is explored by examining the ability of the N—X...N network to bind Na+. Likewise, molecular self-assembly structures driven by the weaker C—X...N halogen-bonding interactions are investigated and the results compared with those of their N—X...N counterparts.

Cooperative halogen bonding and polarized π-stacking in the formation of coloured charge-transfer co-crystals

2018 ◽  
Vol 42 (13) ◽  
pp. 10615-10622 ◽  
Author(s):  
Chideraa I. Nwachukwu ◽  
Zachary R. Kehoe ◽  
Nathan P. Bowling ◽  
Erin D. Speetzen ◽  
Eric Bosch
Keyword(s):  
Charge Transfer ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Π Stacking

Matched electron rich halogen bond acceptors and donor have been synthesized and the halogen bonded charge transfer cocrystals characterized.

Tetradentate halogen bonding macrocyclic anion receptor inspired by the “Texas-sized” molecular box

2022 ◽  
Author(s):  
Tian Zhao ◽  
Vincent Lynch ◽  
Jonathan L. Sessler
Keyword(s):  
Click Chemistry ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Anion Receptor

Inspired by the tetracationic “Texas-sized” molecular box, a neutral analogue containing four iodotriazole halogen bond-promoting subunits (“Ibox”) was synthesized. This new macrocycle was prepared by means of azide-alkyne click chemistry....

Halogen Bonding Organocatalysis Enhanced through Intramolecular Hydrogen Bonds

2022 ◽  
Author(s):  
Asia Marie S Riel ◽  
Daniel Adam Decato ◽  
Jiyu Sun ◽  
Orion Berryman
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Halogen Bond ◽  
Direct Interaction ◽  
Halogen Bonding ◽  
Intramolecular Hydrogen Bonds ◽  
Intramolecular Hydrogen

Recent results indicate a halogen bond donor is strengthened through direct interaction with a hydrogen bond to the electron-rich belt of the halogen. Here, this Hydrogen Bond enhanced Halogen Bond...

scholarly journals Halogen-Bonded Guanine Base Pairs, Quartets and Ribbons

2020 ◽  
Vol 21 (18) ◽  
pp. 6571
Author(s):  
Nicholas J. Thornton ◽  
Tanja van Mourik
Keyword(s):  
Base Pair ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Dna Bases ◽  
Halogen Bonds ◽  
Base Pairs ◽  
Rich Diversity ◽  
Different Types ◽  
Guanine Base ◽  
The Stability

Halogen bonding is studied in different structures consisting of halogenated guanine DNA bases, including the Hoogsteen guanine–guanine base pair, two different types of guanine ribbons (R-I and R-II) consisting of two or three monomers, and guanine quartets. In the halogenated base pairs (except the Cl-base pair, which has a very non-planar structure with no halogen bonds) and R-I ribbons (except the At trimer), the potential N-X•••O interaction is sacrificed to optimise the N-X•••N halogen bond. In the At trimer, the astatines originally bonded to N1 in the halogen bond donating guanines have moved to the adjacent O6 atom, enabling O-At•••N, N-At•••O, and N-At•••At halogen bonds. The brominated and chlorinated R-II trimers contain two N-X•••N and two N-X•••O halogen bonds, whereas in the iodinated and astatinated trimers, one of the N-X•••N halogen bonds is lost. The corresponding R-II dimers keep the same halogen bond patterns. The G-quartets display a rich diversity of symmetries and halogen bond patterns, including N-X•••N, N-X•••O, N-X•••X, O-X•••X, and O-X•••O halogen bonds (the latter two facilitated by the transfer of halogens from N1 to O6). In general, halogenation decreases the stability of the structures. However, the stability increases with the increasing atomic number of the halogen, and the At-doped R-I trimer and the three most stable At-doped quartets are more stable than their hydrogenated counterparts. Significant deviations from linearity are found for some of the halogen bonds (with halogen bond angles around 150°).

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