scholarly journals A Robust Supramolecular Heterosynthon Assembled by a Hydrogen Bond and a Chalcogen Bond

Crystals ◽  
2021 ◽  
Vol 11 (11) ◽  
pp. 1309
Author(s):  
Shaobin Miao ◽  
Yunfan Zhang ◽  
Linjie Shan ◽  
Mingyuan Xu ◽  
Jian-Ge Wang ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Crystal Structures ◽  
Quantum Chemical Calculations ◽  
Quantum Chemical ◽  
Noncovalent Interactions ◽  
Isophthalic Acid ◽  
Stacking Interactions ◽  
Chalcogen Bond ◽  
Good Agreement

The 1:1 and 2:1 cocrystals of isophthalic acid and 2,1,3-benzoselenadiazole have been successfully synthesized and resolved; the noncovalent interactions in the crystal structures have been studied in detail by quantum chemical calculations. In both of the crystal structures, isophthalic acid and 2,1,3-benzoselenadiazole are bound together by a cyclic supramolecular heterosynthon assembled by an O–H···N hydrogen bond and a N–Se···O chalcogen bond. The crystal structures of the 1:1 and 2:1 cocrystals of isophthalic acid and 2,1,3-benzoselenadiazole and the crystal structure of pure isophthalic acid are very similar, which indicates that the [COOH]···[Se−N] cyclic heterosynthon can be an effective alternative to the strong [COOH]2 cyclic homosynthon. The quantum theory of atoms in molecules further recognizes the existence of the hydrogen bond and chalcogen bond. The results of quantum chemical calculations show that the strengths of the π···π stacking interactions in the 1:1 cocrystals of isophthalic acid and 2,1,3-benzoselenadiazole are almost the same as those in the 2:1 cocrystals of isophthalic acid and 2,1,3-benzoselenadiazole, and the strengths of the [COOH]···[Se−N] cyclic heterosynthons (about 9.00 kcal/mol) are less than the strengths of the much stronger [COOH]2 cyclic homosynthons (14.00 kcal/mol). These calculated results are in good agreement with those experimentally observed, demonstrating that, although not as strong as the [COOH]2 cyclic homosynthon, the [COOH]···[Se−N] cyclic heterosynthon can also play a key role in the crystal growth and design.

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.

Stacking interactions of resonance-assisted hydrogen-bridged rings and C6-aromatic rings

2020 ◽  
Vol 22 (24) ◽  
pp. 13721-13728 ◽  
Author(s):  
Jelena P. Blagojević Filipović ◽  
Michael B. Hall ◽  
Snežana D. Zarić
Keyword(s):  
Crystal Structures ◽  
Quantum Chemical Calculations ◽  
Quantum Chemical ◽  
Cambridge Structural Database ◽  
Stacking Interactions ◽  
Aromatic Rings ◽  
Structural Database

Stacking interactions between six-membered resonance-assisted hydrogen-bridged (RAHB) rings and C6-aromatic rings have been studied by analyzing crystal structures in the Cambridge Structural Database and performing quantum chemical calculations.

scholarly journals Crystal structure of 2-oxo-2H-chromen-7-yl 4-fluorobenzoate

2018 ◽  
Vol 74 (5) ◽  
pp. 761-765 ◽  
Author(s):  
Akoun Abou ◽  
Jules Yoda ◽  
Abdoulaye Djandé ◽  
Stéphane Coussan ◽  
T. Jérémie Zoueu
Keyword(s):  
Crystal Structure ◽  
Benzene Ring ◽  
Quantum Chemical ◽  
Theoretical Data ◽  
Acute Angle ◽  
Hirshfeld Surface ◽  
Supramolecular Interactions ◽  
Stacking Interactions ◽  
Compound C ◽  
Good Agreement

In the title compound, C16H9FO4, (I), the benzene ring is oriented at an acute angle of 59.03 (15)° relative to the coumarin plane (r.m.s deviation = 0.009 Å). This conformation of (I) is stabilized by an intramolecular C—H...O hydrogen bond, which closes a five-membering ring. In the crystal, molecules of (I) form infinite zigzag chains along the b-axis direction, linked by C—H...O hydrogen bonds. Furthermore, the crystal structure is supported by π–π stacking interactions between neighbouring pyrone and benzene or coumarin rings [centroid–centroid distances in the range 3.5758 (18)–3.6115 (16) Å], as well as C=O...π interactions [O...centroid distances in the range 3.266 (3)–3.567 (3) Å]. The theoretical data for (I) obtained from quantum chemical calculations are in good agreement with the observed structure, although the calculated C—O—C—C torsion angle between the coumarin fragment and the benzene ring (73.7°) is somewhat larger than the experimental value [63.4 (4)°]. Hirshfeld surface analysis has been used to confirm and quantify the supramolecular interactions.

Non-covalent interactions with inverted carbon: a carbo-hydrogen bond or a new type of hydrogen bond?

2020 ◽  
Vol 22 (16) ◽  
pp. 8988-8997 ◽  
Author(s):  
Juhi Dutta ◽  
Dipak Kumar Sahoo ◽  
Subhrakant Jena ◽  
Kiran Devi Tulsiyan ◽  
Himansu S. Biswal
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Quantum Chemical Calculations ◽  
Structure Analysis ◽  
Quantum Chemical ◽  
Crystal Structure Analysis ◽  
Covalent Interaction ◽  
New Type ◽  
Non Covalent Interactions ◽  
Covalent Interactions

Crystal structure analysis and quantum chemical calculations enabled us to discover a new non-covalent interaction, coined as carbo-hydrogen bond (CH-bond).

scholarly journals Study of stacking interactions between two neutral tetrathiafulvalene molecules in Cambridge Structural Database crystal structures and by quantum chemical calculations

2019 ◽  
Vol 75 (1) ◽  
pp. 1-7 ◽  
Author(s):  
Ivana S. Antonijević ◽  
Dušan P. Malenov ◽  
Michael B. Hall ◽  
Snežana D. Zarić
Keyword(s):  
Crystal Structures ◽  
Quantum Chemical Calculations ◽  
Quantum Chemical ◽  
Energy Surface ◽  
Organic Conductors ◽  
Electron Donors ◽  
Cambridge Structural Database ◽  
Stacking Interactions ◽  
Structural Database ◽  
Calculated Potential Energy

Tetrathiafulvalene (TTF) and its derivatives are very well known as electron donors with widespread use in the field of organic conductors and superconductors. Stacking interactions between two neutral TTF fragments were studied by analysing data from Cambridge Structural Database crystal structures and by quantum chemical calculations. Analysis of the contacts found in crystal structures shows high occurrence of parallel displaced orientations of TTF molecules. In the majority of the contacts, two TTF molecules are displaced along their longer C 2 axis. The most frequent geometry has the strongest TTF–TTF stacking interaction, with CCSD(T)/CBS energy of −9.96 kcal mol−1. All the other frequent geometries in crystal structures are similar to geometries of the minima on the calculated potential energy surface.

scholarly journals The Face-to-Face σ-Hole···σ-Hole Stacking Interactions: Structures, Energies, and Nature

Crystals ◽  
2021 ◽  
Vol 11 (8) ◽  
pp. 877
Author(s):  
Yu Zhang ◽  
Weizhou Wang
Keyword(s):  
Quantum Chemical ◽  
Noncovalent Interactions ◽  
Electrostatic Energy ◽  
Stacking Interactions ◽  
Energy Component ◽  
Stacking Interaction ◽  
Face To Face ◽  
The Face ◽  
Π Stacking Interaction ◽  
Induction Energy

The existence of the π···π stacking interaction is well-known. Similarly, it is reasonable to assume the existence of the σ-hole···σ-hole stacking interaction. In this work, the structures, energies, and nature of the face-to-face σ-hole···σ-hole stacking interactions in the crystal structures have been investigated in detail by the quantum chemical calculations. The calculated results clearly show that the face-to-face σ-hole···σ-hole stacking interactions exist and have unique properties, although their strengths are not very significant. The energy component analysis reveals that, unlike many other dispersion-dominated noncovalent interactions in which the induction energies always play minor roles for their stabilities, for the face-to-face σ-hole···σ-hole stacking interaction the contribution of the induction energy to the total attractive energy is close to or even larger than that of the electrostatic energy. The structures, energies, and nature of the face-to-face σ-hole···σ-hole stacking interactions confined in small spaces have also been theoretically simulated. One of the important findings is that encapsulation of the complex bound by the face-to-face σ-hole···σ-hole stacking interaction can tune the electronic properties of the container.

Sign in / Sign up

Export Citation Format

Share Document