Stacking Interactions of Resonance-Assisted Hydrogen-Bridged Rings. A Systematic Study of Crystal Structures and Quantum-Chemical Calculations

2019 ◽  
Vol 19 (10) ◽  
pp. 5619-5628 ◽  
Author(s):  
Jelena P. Blagojević Filipović ◽  
Michael B. Hall ◽  
Snežana D. Zarić
Keyword(s):  
Crystal Structures ◽  
Quantum Chemical Calculations ◽  
Systematic Study ◽  
Quantum Chemical ◽  
Stacking Interactions

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 Stacking interactions between hydrogen-bridged and aromatic rings: study of crystal structures and quantum chemical calculations

CrystEngComm ◽  
2017 ◽  
Vol 19 (1) ◽  
pp. 40-46 ◽  
Author(s):  
Jelena P. Blagojević ◽  
Dušan Ž. Veljković ◽  
Snežana D. Zarić
Keyword(s):  
Crystal Structures ◽  
Quantum Chemical Calculations ◽  
Quantum Chemical ◽  
Stacking Interactions ◽  
Aromatic Rings

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 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.

Cyclisierung von Di(tert-butyl-methyl)ketazin zu 1,2-Diaza-3-bora- und 1,2-Diaza-3-sila-cyclopent-5-enen / Cyclization of Di(tert-butyl-methyl)ketazine to 1,2-Diaza-3-bora- and 1,2-Diaza-3-sila-cyclopent-5-enes

2006 ◽  
Vol 61 (10) ◽  
pp. 1261-1274 ◽  
Author(s):  
Florian Armbruster ◽  
Nina Armbruster ◽  
Uwe Klingebiel ◽  
Mathias Noltemeyer ◽  
Stefan Schmatz
Keyword(s):  
Crystal Structures ◽  
Quantum Chemical Calculations ◽  
Chlorine Atom ◽  
Quantum Chemical ◽  
Membered Ring ◽  
Substitution Product ◽  
Tert Butyl ◽  
Isomeric Structures

The results of quantum chemical calculations on lithium ketazides suggest mainly four isomeric structures with different modes of lithium coordination (A-D). A monolithium ketazide thf-adduct (1) was isolated supporting the results of the quantum chemical calculations. In reactions of the lithiated di(tert-butyl-methyl)ketazine with BCl3 and Cl2BPh, 1,2-aza-azonia-3-borata-cyclopent-5-enes (2, 3) were isolated. Substitution of a chlorine atom of 2 and 3 with t-BuLi leads to the formation of derivatives 4 and 5. HCl elimination from 2 with Et3N gives - via a diazaboracyclopentene (6) - a bicyclus 7. In the reaction of the dilithiated ketazine with F2BN(SiMe3)2, the diaza-boracyclopentene 8 is obtained while with Cl4Si, F3SiN(SiMe3)2, and Cl2SiMe2 the diazasilacyclopentenes 9 - 11 are generated. SiF4 reacts with the dilithium ketazide to give a spirocyclus (12). The monolithium ketazide and Cl2SiMe2 react at 30 °C to give a four-membered ring isomer of the substitution product which is formed via a 1,3-chlorine shift from silicon to carbon (13). A tetrameric silanolate was isolated as a by-product in this reaction. It gives evidence for the structure of lithium ketazide A. Crystal structures of 5, 7, 10, and 14 are reported.

Halogen bonds as a tool in the design of high energetic materials: evidence from crystal structures and quantum chemical calculations

CrystEngComm ◽  
2021 ◽  
Author(s):  
Aleksandra B. Đunović ◽  
Dušan Ž Veljković
Keyword(s):  
Crystal Structures ◽  
Quantum Chemical Calculations ◽  
Electrostatic Potential ◽  
Energetic Materials ◽  
Quantum Chemical ◽  
Central Area ◽  
Molecular Surface ◽  
Halogen Bonds ◽  
Positive Electrostatic Potential

Positive electrostatic potential over the central area of the molecular surface is one of the main characteristics of high energetic materials (HEM) that determines their sensitivity towards detonation. The influence...

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.

Influence of ortho-substituent on the molecular and crystal structures of 2-(N-arylimino)coumarin-3-carboxamide: isotypic and polymorphic structures

2019 ◽  
Vol 75 (5) ◽  
pp. 887-902 ◽  
Author(s):  
Svitlana V. Shishkina ◽  
Irina S. Konovalova ◽  
Sergiy M. Kovalenko ◽  
Pavlo V. Trostianko ◽  
Anna O. Geleverya ◽  
...  
Keyword(s):  
Crystal Structures ◽  
Quantum Chemical Calculations ◽  
Quantum Chemical ◽  
Polymorphic Modification ◽  
Aryl Group ◽  
Group Iii ◽  
Pairwise Interactions ◽  
Group I ◽  
Polymorphic Modifications ◽  
Molecular And Crystal Structures

During a comprehensive study of a series of 2-(N-arylimino)coumarin-3-carboxamides with the aryl group substituted in the ortho-position by either a halogen atom, a methyl group or a methoxy group, the existence of three groups of isotypic crystal structures has been revealed. The similarity of crystal structures belonging to the same groups was confirmed by the analysis based on the comparison of pairwise interactions energies obtained from quantum chemical calculations. Group I includes unsubstituted, methyl-substituted and polymorphic modification 1 of fluoro-substituted 2-(N-arylimino)coumarin-3-carboxamide. Structures of polymorphic modification 2 of fluoro-substituted derivative, chloro-substituted and polymorphic modification 1 of bromo-substituted 2-(N-arylimino)coumarin-3-carboxamide may represent group II. Group III contains structures of polymorphic modification 2 of bromo-substituted derivative, iodine- and methoxy-substituted 2-(N-arylimino)coumarin-3-carboxamides. Structures of the same type group have extremely close parameters of the unit cell as well as those of molecular and crystal structures. But they are not identical. Polymorphic modifications of fluoro- and bromo-substituted 2-(N-arylimino)coumarin-3-carboxamides belong to different crystal types mainly due to different arrangement of basic structural motifs separated out using quantum chemical calculations.

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