A Neutral Donor-Acceptor p-Stack: Solid-State Structures of 1 : 1 Pyromellitic Diimide-Dialkoxynaphthalene Cocrystals

1997 ◽  
Vol 50 (5) ◽  
pp. 439 ◽  
Author(s):  
Darren G. Hamilton ◽  
Daniel E. Lynch ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Neutral Donor ◽  
Hydrogen Bonding Interactions ◽  
Donor And Acceptor ◽  
Structural Preferences ◽  
Donor Acceptor ◽  
Covalently Linked ◽  
Solid State Structures

Pyromellitic diimide forms orange-coloured cocrystals of 1 : 1 stoichiometry with dialkoxynaphthalene derivatives. The solid-state structures of two examples are presented. The cocrystal formed with 2,6-dimethoxynaphthalene presents vertical stacks of alternating π-rich and π-deficient subunits with the long axes of the respective components approximately parallel. Investigation of the packing in the cocrystal also reveals a stabilizing array of hydrogen bonds between the components of adjacent stacks. Cocrystallization with 1,5-[2-(2-hydroxyethoxy)ethoxy]naphthalene, a derivative bearing hydroxy terminated ethyleneoxy chains, gives rise to an altered structural arrangement. Alternating donor- acceptor stacks once again dominate the structure but adopt a geometry where the long axes of the constituents are essentially perpendicular. Hydrogen-bonding interactions result in the formation of continuous non-covalently linked columns of donor and acceptor subunits by linking the terminal hydroxy functions of the naphthalene component to the imide protons. The structural preferences revealed by these solid-state analyses indicate that these complexes are useful prototypes of more complex neutral supramolecular assemblies.

scholarly journals {N 1-[2-(Butylselanyl)benzyl]-N 2,N 2-dimethylethane-1,2-diamine}dichloridomercury(II)

2018 ◽  
Vol 74 (8) ◽  
pp. 1151-1154
Author(s):  
Pushpendra Singh ◽  
Harkesh B. Singh ◽  
Ray J. Butcher
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Self Assembly ◽  
Title Compound ◽  
Supramolecular Assembly ◽  
Molecular Geometry ◽  
The Self ◽  
Intermolecular Hydrogen Bonding ◽  
Hydrogen Bonding Interactions ◽  
Donor Acceptor

In the title compound, [HgCl2(C16H28N2Se)], the primary geometry around the Se and Hg atoms is distorted trigonal–pyramidal and distorted square-pyramidal, respectively. The distortion of the molecular geometry in the complex is caused by the steric demands of the ligands attached to the Se atom. The Hg atom is coordinated through two chloride anions, an N atom and an Se atom, making up an unusual HgNSeCl2 coordination sphere with an additional long Hg...N interaction. Intermolecular C—H...Cl interactions are the only identified intermolecular hydrogen-bonding interactions that seem to be responsible for the self assembly. These relatively weak C—H...Cl hydrogen bonds possess the required linearity and donor–acceptor distances. They act as molecular associative forces that result in a supramolecular assembly along the b-axis direction in the solid state of the title compound.

The design of artificial receptors for complexation and controlled aggregation

1993 ◽  
Vol 345 (1674) ◽  
pp. 57-66 ◽  
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Complex Formation ◽  
Hydrogen Bonds ◽  
Synthetic Receptors ◽  
Polar Solvents ◽  
Artificial Receptors ◽  
Hydrogen Bonding Interactions ◽  
Number Of Factors ◽  
Network Of Hydrogen Bonds

Simple synthetic receptors have been developed that function via directed hydrogen bonding interactions in highly competitive solvents. Strong binding of this type in polar solvents may be due to a number of factors including favourable secondary hydrogen bonding interactions between the carboxylate and urea, the use of charged H-bond acceptors, an inefficient solvation of the closely spaced H-bond donor sites in the urea, and an entropically favourable release of solvent and/or counterion molecules on complex formation. We also demonstrate that these types of interactions can be used to induce, both in solution and the solid state, discrete 2 + 2 aggregates stabilized by a network of hydrogen bonds.

Hydrogen Bonding of two l-(φ-Ammonioalkyl)-2-acyl-cyclopentadienides in the Solid State

2000 ◽  
Vol 55 (6) ◽  
pp. 541-545 ◽  
Author(s):  
Andreas Müller ◽  
Gerhard Maas
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Two Dimensional ◽  
Intermolecular Hydrogen Bonds ◽  
Dimensional Network ◽  
Solid State Structures ◽  
Centrosymmetric Dimers

The solid-state structures of a l-(φ-ammoniopropyl)-2-(2-thienylcarbonyl)-cyclopentadienide (2) and a l-(φ-ammoniopentyl)-2-(4-methoxybenzoyl)-cyclopentadienide (3) have been determined. Both betaines self-assemble by NH ··· O hydrogen bonds, but the motifs are different. In the ammoniopropyl case, both intramolecular and intermolecular hydrogen bonds of this type exist, the latter bond being responsible for the formation of infinite chains. In the ammoniopentyl case, intermolecular hydrogen bonds build up a two-dimensional network which contains centrosymmetric dimers held together by NH ··· O=C-aryl hydrogen bonds.

Synthesis and Solid-State Structures of Alkyl-Substituted 3-Cyano-2-pyridones

2004 ◽  
Vol 59 (10) ◽  
pp. 1121-1131 ◽  
Author(s):  
Christian B. Fischer ◽  
Kurt Polborn ◽  
Harald Steininger ◽  
Hendrik Zipse
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
External Influence ◽  
Hydrogen Bonding Interactions ◽  
Group A ◽  
Group B ◽  
Solid State Structures

AbstractA series of 3-cyano-pyridones carrying a variety of alkyl substituents at C-5 and C-6 has been synthesized and their solid-state structures have been studied. Hydrogen bonding interactions between individual pyridone molecules lead either to the formation of symmetric dimers of the R22 (8) type or to helical chains of the C(4) type. Based on known and calculated structures for the 2-pyridone parent system, the solid-state structures can be divided in two groups representing cases with little external influence on the hydrogen bonding array (group A) and those with a larger external influence (group B).

A Neutral Donor-Acceptor p-Stack: Solid-State Structures of 1 : 1 Pyromellitic Diimide-Dialkoxynaphthalene Cocrystals

1997 ◽  
Vol 50 (4) ◽  
pp. 271 ◽  
Author(s):  
Rina Carlini ◽  
Cheng-Lin Fang ◽  
Deborah Herrington ◽  
Kerianne Higgs ◽  
Russell Rodrigo ◽  
...  
Keyword(s):  
Solid State ◽  
Diels Alder ◽  
Hypervalent Iodine ◽  
One Pot ◽  
Neutral Donor ◽  
Donor Acceptor ◽  
Solid State Structures

Substituted ortho-benzoquinones, generated in situ by hypervalent iodine oxidation of catechols, are intercepted by unsymmetrical dienes to provide Diels-Alder adducts with complete regiospecificity. Catechols with carboxy substituents in the 3 or 4 positions react similarly and the initial adducts decarboxylate to produce 8-substituted or 5-substituted 1,2-dihydroxydihydronaphthalenes respectively, in a one-pot three-step sequence. The reaction has been further adapted to produce naphtho[1,8-bc]furans in a one-pot process; its application towards the synthesis of the tricyclic system of the sesquiterpene nardonoxide is described

scholarly journals Functional materials based on molecules with hydrogen-bonding ability: applications to drug co-crystals and polymer complexes

2018 ◽  
Vol 5 (6) ◽  
pp. 180564 ◽  
Author(s):  
Kristin M. Hutchins
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Functional Materials ◽  
Polymeric Materials ◽  
Pharmaceutical Compounds ◽  
Multiple Point ◽  
Polymer Complexes ◽  
Design Synthesis ◽  
Hydrogen Bonding Interactions ◽  
Donor Acceptor

The design, synthesis and property characterization of new functional materials has garnered interest in a variety of fields. Materials that are capable of recognizing and binding with small molecules have applications in sensing, sequestration, delivery and property modification. Specifically, recognition of pharmaceutical compounds is of interest in each of the aforementioned application areas. Numerous pharmaceutical compounds comprise functional groups that are capable of engaging in hydrogen-bonding interactions; thus, materials that are able to act as hydrogen-bond receptors are of significant interest for these applications. In this review, we highlight some crystalline and polymeric materials that recognize and engage in hydrogen-bonding interactions with pharmaceuticals or small biomolecules. Moreover, as pharmaceuticals often exhibit multiple hydrogen-bonding sites, many donor/acceptor molecules have been specifically designed to interact with the drug via such multiple-point hydrogen bonds. The formation of multiple hydrogen bonds not only increases the strength of the interaction but also affords unique hydrogen-bonded architectures.

A New Hydrogen-Bonding Motif with Constituents Bearing Donor and Acceptor Sites 7 Å Apart

2005 ◽  
Vol 60 (7) ◽  
pp. 758-762 ◽  
Author(s):  
Katja Heinze ◽  
Anja Reinhart
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Nitrogen Atom ◽  
Hydrogen Bonds ◽  
Hydrogen Donor ◽  
Para Position ◽  
Hydrogen Acceptor ◽  
Aryl Ring ◽  
Donor And Acceptor ◽  
Pyrrole Nitrogen

Aryl substituted dipyrromethanes [di(pyrrol-2-yl)-phenyl-methanes] with hydrogen acceptor substituents R in para position of the aryl ring [R = CO2Me, CO2H, CONH(iPr) and NH2] located 7 Å apart from the hydrogen donor pyrrole nitrogen atom are shown to self-assemble in the solid state via hydrogen bonds to form rings or chains.

Supramolecular control of organic p/n-heterojunctions by complementary hydrogen bonding

2014 ◽  
Vol 174 ◽  
pp. 297-312 ◽  
Author(s):  
Hayden T. Black ◽  
Huaping Lin ◽  
Francine Bélanger-Gariépy ◽  
Dmitrii F. Perepichka
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Organic Semiconductors ◽  
Crystal Engineering ◽  
Self Assembly ◽  
Structural Control ◽  
Molecular Structures ◽  
Mutual Arrangement ◽  
Donor And Acceptor ◽  
Donor Acceptor

The supramolecular structure of organic semiconductors (OSCs) is the key parameter controlling their performance in organic electronic devices, and thus methods for controlling their self-assembly in the solid state are of the upmost importance. Recently, we have demonstrated the co-assembly of p- and n-type organic semiconductors through a three-point hydrogen-bonding interaction, utilizing an electron-rich dipyrrolopyridine (P2P) heterocycle which is complementary to naphthalenediimides (NDIs) both in its electronic structure and H bonding motif. The hydrogen-bonding-mediated co-assembly between P2P donor and NDI acceptor leads to ambipolar co-crystals and provides unique structural control over their solid-state packing characteristics. In this paper we expand our discussion on the crystal engineering aspects of H bonded donor–acceptor assemblies, reporting three new single co-crystal X-ray diffraction structures and analyzing the different packing characteristics that arise from the molecular structures employed. Particular attention is given toward understanding the formation of the two general motifs observed, segregated and mixed stacks. Co-assembly of the donor and acceptor components into a single, crystalline material, allows the creation of ambipolar semiconductors where the mutual arrangement of p- and n-conductive channels is engineered by supramolecular design based on complementary H bonding.

Cocrystals of 5-fluorocytosine. I. Coformers with fixed hydrogen-bonding sites

2012 ◽  
Vol 68 (4) ◽  
pp. 431-443 ◽  
Author(s):  
Maya Tutughamiarso ◽  
Guido Wagner ◽  
Ernst Egert
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Antiviral Drug ◽  
The Other ◽  
Receptor Interaction ◽  
Dimer Formation ◽  
Hydrogen Bonding Interactions ◽  
Donor Acceptor ◽  
Drug Receptor ◽  
Drug Receptor Interaction

The antifungal drug 5-fluorocytosine (4-amino-5-fluoro-1,2-dihydropyrimidin-2-one) was cocrystallized with five complementary compounds in order to better understand its drug–receptor interaction. The first two compounds, 2-aminopyrimidine (2-amino-1,3-diazine) and N-acetylcreatinine (N-acetyl-2-amino-1-methyl-5H-imidazol-4-one), exhibit donor–acceptor sites for R 2 2(8) heterodimer formation with 5-fluorocytosine. Such a heterodimer is observed in the cocrystal with 2-aminopyrimidine (I); in contrast, 5-fluorocytosine and N-acetylcreatinine [which forms homodimers in its crystal structure (II)] are connected only by a single hydrogen bond in (III). The other three compounds 6-aminouracil (6-amino-2,4-pyrimidinediol), 6-aminoisocytosine (2,6-diamino-3H-pyrimidin-4-one) and acyclovir [acycloguanosine or 2-amino-9-[(2-hydroxyethoxy)methyl]-1,9-dihydro-6H-purin-6-one] possess donor–donor–acceptor sites; therefore, they can interact with 5-fluorocytosine to form a heterodimer linked by three hydrogen bonds. In the cocrystals with 6-aminoisocytosine (Va)–(Vd), as well as in the cocrystal with the antiviral drug acyclovir (VII), the desired heterodimers are observed. However, they are not formed in the cocrystal with 6-aminouracil (IV), where the components are connected by two hydrogen bonds. In addition, a solvent-free structure of acyclovir (VI) was obtained. A comparison of the calculated energies released during dimer formation helped to rationalize the preference for hydrogen-bonding interactions in the various cocrystal structures.

scholarly journals Analysis of energies of halogen and hydrogen bonding interactions in the solid state structures of vanadyl Schiff base complexes

RSC Advances ◽  
2019 ◽  
Vol 9 (9) ◽  
pp. 4789-4796 ◽  
Author(s):  
Snehasish Thakur ◽  
Michael G. B. Drew ◽  
Antonio Franconetti ◽  
Antonio Frontera ◽  
Shouvik Chattopadhyay
Keyword(s):  
Hydrogen Bonding ◽  
Schiff Base ◽  
Solid State ◽  
Dft Calculations ◽  
Schiff Base Complexes ◽  
Supramolecular Interactions ◽  
Computational Tool ◽  
Hydrogen Bonding Interactions ◽  
Solid State Structures

Four vanadyl Schiff base complexes have been prepared and characterized. Energies of supramolecular interactions in complexes 1, 2 and 3 were estimated using DFT calculations, and further corroborated with NCI plot index computational tool.

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