Halogen Bonding Directed Supramolecular Quadruple and Double Helices from Hydrogen-Bonded Arylamide Foldamers

2018 ◽  
Vol 58 (1) ◽  
pp. 226-230 ◽  
Author(s):  
Chuan-Zhi Liu ◽  
Satish Koppireddi ◽  
Hui Wang ◽  
Dan-Wei Zhang ◽  
Zhan-Ting Li
Keyword(s):  
Halogen Bonding ◽  
Double Helices ◽  
Arylamide Foldamers ◽  
Hydrogen Bonded

Halogen and hydrogen bonding-driven self-assembly of supramolecular macrocycles and double helices from hydrogen-bonded arylamide foldamers

CrystEngComm ◽  
2019 ◽  
Vol 21 (16) ◽  
pp. 2626-2630 ◽  
Author(s):  
Satish Koppireddi ◽  
Chuan-Zhi Liu ◽  
Hui Wang ◽  
Dan-Wei Zhang ◽  
Zhan-Ting Li
Keyword(s):  
Hydrogen Bonding ◽  
Self Assembly ◽  
Halogen Bonding ◽  
Double Helices ◽  
Aromatic Amide ◽  
Arylamide Foldamers ◽  
Hydrogen Bonded

Halogen bonding has been used to hold hydrogen bonded short aromatic amide foldamers to form 2 + 2 or 1 + 1 macrocycles.

Halogen Bonding Directed Supramolecular Quadruple and Double Helices from Hydrogen-Bonded Arylamide Foldamers

2018 ◽  
Vol 131 (1) ◽  
pp. 232-236 ◽  
Author(s):  
Chuan-Zhi Liu ◽  
Satish Koppireddi ◽  
Hui Wang ◽  
Dan-Wei Zhang ◽  
Zhan-Ting Li
Keyword(s):  
Halogen Bonding ◽  
Double Helices ◽  
Arylamide Foldamers ◽  
Hydrogen Bonded

Taking the halogen bonding–hydrogen bonding competition one step further: complexes of difluoroiodomethane with trimethylphosphine, dimethyl sulfide and chloromethane

2017 ◽  
Vol 73 (2) ◽  
pp. 168-178 ◽  
Author(s):  
Yannick Geboes ◽  
Frank De Proft ◽  
Wouter A. Herrebout
Keyword(s):  
Hydrogen Bonding ◽  
Dimethyl Sulfide ◽  
Halogen Bonding ◽  
Hydrogen Bond Donor ◽  
Lewis Bases ◽  
One Step ◽  
Fourier Transform Ir ◽  
Binary Associations ◽  
Bonded Complexes ◽  
Hydrogen Bonded

To rationalize the driving factors in the competition of halogen bonding and hydrogen bonding, the complexes of the combined halogen-/hydrogen-bond donor difluoroiodomethane with the Lewis bases trimethylphosphine, dimethyl sulfide and chloromethane are studied. For all Lewis bases,ab initiocalculations lead to halogen- and hydrogen-bonded complexes. Fourier transform–IR experiments involving solutions of mixtures of difluoroiodomethane with trimethylphosphine(-d9) or dimethyl sulfide(-d6) in liquid krypton confirm the coexistence of a halogen-bonded and hydrogen-bonded complex. Also for solutions containing chloromethane, evidence of the formation of binary associations is found, but no definitive assignment of the multiple complex bands could be made. Using van't Hoff plots, the experimental complexation enthalpies for the halogen- and hydrogen-bonded complex of difluoroiodomethane with trimethylphosphine are determined to be −15.4 (4) and −10.5 (3) kJ mol−1, respectively, while for the halogen- and hydrogen-bonded complexes with dimethyl sulfide, the values are −11.3 (5) and −7.7 (6) kJ mol−1, respectively. The experimental observation that for both trimethylphospine and dimethyl sulfide the halogen-bonded complex is more stable than the hydrogen-bonded complex supports the finding that softer Lewis bases tend to favor iodine halogen bonding over hydrogen bonding.

scholarly journals An investigation to elucidate the factors dictating the crystal structure of seven ammonium carboxylate molecular salts

2018 ◽  
Vol 74 (5) ◽  
pp. 580-586 ◽  
Author(s):  
Jacques Blignaut ◽  
Andreas Lemmerer
Keyword(s):  
Hydrogen Bonds ◽  
Functional Group ◽  
Halogen Bonding ◽  
Hydrogen Bond Acceptor ◽  
One Dimensional ◽  
Ladder System ◽  
Molecular Salts ◽  
Additional Hydrogen Bond ◽  
Additional Hydrogen ◽  
Hydrogen Bonded

The crystal structures of seven ammonium carboxylate salts are reported, namely (RS)-1-phenylethan-1-aminium isonicotinate, C8H12N+·C6H4N1O2 −, (I), (RS)-1-phenylethan-1-aminium flurbiprofenate [or 2-(3-fluoro-4-phenylphenyl)propanoate], C8H12N+·C15H12FO2 −, (II), (RS)-1-phenylethan-1-aminium 2-chloro-4-nitrobenzoate, C8H12N+·C7H3ClNO4 −, (III), (RS)-1-phenylethan-1-aminium 4-iodobenzoate, C8H12N+·C7H4IO2 −, (IV), (S)-1-cyclohexylethan-1-aminium 2-chloro-4-nitrobenzoate, C8H18N+·C7H3ClNO4 −, (V), 2-(cyclohex-1-en-1-yl)ethan-1-aminium 4-bromobenzoate, C8H16N+·C7H4BrO2 −, (VI), and (S)-1-cyclohexylethan-1-aminium 4-bromobenzoate, C8H18N+·C7H4BrO2 −, (VII). Salts (II) to (VII) feature three N+—H...O− hydrogen bonds, which form one-dimensional hydrogen-bonded ladders. Salts (II), (III), (IV), (V) and (VII) have a type II ladder system despite the presence of halogen bonding and other intermolecular interactions, whereas (VI) has a type III ladder system. Salt (I) has a unique hydrogen-bonded system of ladders, featuring both N+—H...O− and N+—H...N hydrogen bonds owing to the presence of the pyridine functional group. The presence of an additional hydrogen-bond acceptor on the carboxylate cation disrupts the formation of the ubiquitous type II and III ladder found predominately in ammonium carboxylate salts. Halogen bonding, however, has no influence on their formation.

scholarly journals The intramolecular hydrogen bonded–halogen bond: a new strategy for preorganization and enhanced binding

2018 ◽  
Vol 9 (26) ◽  
pp. 5828-5836 ◽  
Author(s):  
Asia Marie S. Riel ◽  
Daniel A. Decato ◽  
Jiyu Sun ◽  
Casey J. Massena ◽  
Morly J. Jessop ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Hydrogen Bonding ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
New Strategy ◽  
Intramolecular Hydrogen ◽  
Hydrogen Bonded

Intramolecular hydrogen bonding directly to halogen bond donors preorganizes molecular structure and strengthens halogen bonding.

Supramolecular synthesis with N-hetero-tolanes: liquid crystals and hydrogen-bonded and halogen-bonded co-crystals

CrystEngComm ◽  
2020 ◽  
Vol 22 (3) ◽  
pp. 416-419
Author(s):  
Linda Flores ◽  
Ismael López Duarte ◽  
Berta Gómez-Lor ◽  
Enrique Gutierrez-Puebla ◽  
Gunther Hennrich
Keyword(s):  
Liquid Crystals ◽  
Halogen Bonding ◽  
Crystalline Aggregates ◽  
Hydrogen Bonded

Supramolecular, crystalline aggregates are obtained from EO-active N-hetero-tolanes by protonation or halogen bonding.

Two new CoII coordination polymers with multifunctional 5-amino-2,4,6-tribromoisophthalic acid and flexible isomeric bis(imidazole) ligands: preparation, crystal structure and characterization

2018 ◽  
Vol 74 (4) ◽  
pp. 504-512
Author(s):  
Chang-Kai Su ◽  
Kou-Lin Zhang
Keyword(s):  
Coordination Polymers ◽  
Three Dimensional ◽  
Halogen Bonding ◽  
Supramolecular Network ◽  
Two Dimensional ◽  
Tetrahedral Configuration ◽  
Distorted Octahedral Coordination Geometry ◽  
Distorted Octahedral ◽  
Imidazole Ligands ◽  
Hydrogen Bonded

Two new CoII coordination polymers (CPs), namely, catena-poly[[[(5-amino-2,4,6-tribromobenzene-1,3-dicarboxylato-κO)aquacobalt(II)]-bis[μ-1,3-bis(imidazol-1-ylmethyl)benzene-κ2 N:N′]] 4.75-hydrate], {[Co(C8H2Br3NO4)(C14H14N4)2(H2O)]·4.75H2O} n , (1), and poly[(μ-5-amino-2,4,6-tribromobenzene-1,3-dicarboxylato-κ2 O 1:O 3)[μ-1,2-bis(imidazol-1-ylmethyl)benzene-κ2 N:N′]cobalt(II)], [Co(C8H2Br3NO4)(C14H14N4)] n , (2), have been synthesized successfully by the assembly of multifunctional 5-amino-2,4,6-tribromoisophthalic acid (H2ATBIP) and CoII ions in the presence of the flexible isomeric bis(imidazole) ligands 1,3-bis(imidazol-1-ylmethyl)benzene (mbix) and 1,2-bis(imidazol-1-ylmethyl)benzene (obix). The isomeric mbix and obix ligands have a big influence on the structures of CPs (1) and (2). CP (1) is composed of chains of nanometre-sized elliptical rings, in which the CoII atom exhibits a distorted octahedral coordination geometry and ATBIP2− acts as a monodentate ligand. Two adjacent chains are interlinked by π–π stacking interactions and hydrogen bonds, resulting in a supramolecular double chain. Hydrogen-bonded R 8 6(16) rings extend adjacent supramolecular double chains into a two-dimensional supramolecular layer. Halogen bonding and a hydrogen-bonded R 4 2(8) ring further link the two-dimensional supramolecular layers, leading to the formation of a three-dimensional supramolecular network. The CoII ion in CP (2) is tetracoordinated, exhibiting a distorted tetrahedral configuration. The ATBIP2− ligand exhibits a bis(monodentate) coordination bridging mode, linking adjacent CoII ions into zigzag chains, which are further bridged by the auxiliary bridging obix ligand, resulting in a two-dimensional (4,4) topological network. Interlayer hydrogen and halogen–halogen bonding further extend the two-dimensional layers into a three-dimensional supramolecular network. A detailed analysis of the solid-state UV–Vis–NIR diffuse-reflectance spectra of (1) and (2) indicates that a wide optical band gap exists in both (1) and (2). CP (1) exhibits an irreversible dehydration–rehydration behaviour.

Minimal complementary hydrogen-bonded double helices

2010 ◽  
Vol 46 (39) ◽  
pp. 7343 ◽  
Author(s):  
Hong-Bo Wang ◽  
Bhanu P. Mudraboyina ◽  
Jiaxin Li ◽  
James A. Wisner
Keyword(s):  
Double Helices ◽  
Hydrogen Bonded
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