The typical crystal structures of a few representative α-aryl-α-hydroxyphosphonates

2019 ◽  
Vol 75 (3) ◽  
pp. 283-293 ◽  
Author(s):  
Zita Rádai ◽  
Nóra Zsuzsa Kiss ◽  
Mátyás Czugler ◽  
Konstantin Karaghiosoff ◽  
György Keglevich
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Crystal Structures ◽  
Weak Interactions ◽  
Aryl Group ◽  
Dialkyl Phosphites ◽  
The Pudovik Reaction ◽  
Graph Set ◽  
Graph Sets ◽  
Primary Graph

The crystal structures of seven α-aryl-α-hydroxyphosphonates synthesized by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites, namely dimethyl [(hydroxy)(phenyl)methyl]phosphonate, C9H13O4P, dimethyl [(3,4-dimethoxyphenyl)(hydroxy)methyl]phosphonate, C11H17O6P, dimethyl (1-hydroxy-1-phenylethyl)phosphonate, C10H15O4P, dimethyl [1-hydroxy-1-(4-nitrophenyl)ethyl]phosphonate, C10H14NO6P, dibenzyl [hydroxy(2-nitrophenyl)methyl]phosphonate, C21H20NO6P, dibenzyl [(3-chlorophenyl)(hydroxy)methyl]phosphonate, C21H20ClO4P, and dibenzyl [hydroxy(4-methylphenyl)methyl]phosphonate, C22H23O4P, were studied to gain a better understanding of the organization in this type of molecule in the solid state. The crystals obtained for this series of compounds show a balance between C—OH...O=P chain-linked packing and the dimeric types of hydrogen-bond bridges of intermolecular pairs of such functions. The description is based on primary graph-set descriptors. Using graph-set descriptors one level deeper (i.e. secondary graph sets of the C—H...O type) revealed a similarity in the graph-set descriptors, suggesting a fine interplay of substituent- and shape-dependent effects on strong–weak interactions. It seems that the formation of chains or dimers is governed not only by the presence of a tertiary Cα atom, but also by the nature and crowding of the ortho substituents of the α-aryl group.

scholarly journals Functionalised Terpyridines and Their Metal Complexes—Solid-State Interactions

Chemistry ◽  
2021 ◽  
Vol 3 (1) ◽  
pp. 199-227
Author(s):  
Young Hoon Lee ◽  
Jee Young Kim ◽  
Sotaro Kusumoto ◽  
Hitomi Ohmagari ◽  
Miki Hasegawa ◽  
...  
Keyword(s):  
Solid State ◽  
Metal Complexes ◽  
Crystal Structures ◽  
Weak Interactions ◽  
Dispersion Interactions ◽  
Derivatives Of

Analysis of the weak interactions within the crystal structures of 33 complexes of various 4′-aromatic derivatives of 2,2′:6′,2″-terpyridine (tpy) shows that interactions that exceed dispersion are dominated, as expected, by cation⋯anion contacts but are associated with both ligand–ligand and ligand–solvent contacts, sometimes multicentred, in generally complicated arrays, probably largely determined by dispersion interactions between stacked aromatic units. With V(V) as the coordinating cation, there is evidence that the polarisation of the ligand results in an interaction exceeding dispersion at a carbon bound to nitrogen with oxygen or fluorine, an interaction unseen in the structures of M(II) (M = Fe, Co, Ni, Cu, Zn, Ru and Cd) complexes, except when 1,2,3-trimethoxyphenyl substituents are present in the 4′-tpy.

Heterocyclic Tautomerism. The Solution and Crystal Structures of 1-(4',6'-Dimethylpyrimidin-2'-yl)-3-methylpyrazol-5-ol

1984 ◽  
Vol 37 (2) ◽  
pp. 459 ◽  
Author(s):  
PJ Steel ◽  
AR Whyte
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Crystal Structures ◽  
Intramolecular Hydrogen Bond ◽  
Title Compound ◽  
Intramolecular Hydrogen ◽  
Strong Intramolecular Hydrogen Bond

Both in the solid state and in solution, the title compound is shown to exist as the OH tautomer (3), which is stabilized by a strong intramolecular hydrogen bond. Crystals of the pyrazol-5-ol (3) are monoclinic: P 21/c, a 9.692(5), b 7.371(5), c 15.345(8) �, β 106.07(4)�, Z 4; the structure was refined to R 0.072 and Rw 0.062.

scholarly journals Crystal structures and hydrogen bond analysis of five amino acid conjugates of terephthalic and benzene-1,2,3-tricarboxylic acids

CrystEngComm ◽  
2014 ◽  
Vol 16 (35) ◽  
pp. 8243-8251 ◽  
Author(s):  
Anirban Karmakar ◽  
Clive L. Oliver ◽  
Ana E. Platero-Prats ◽  
Elina Laurila ◽  
Lars Öhrström
Keyword(s):  
Hydrogen Bond ◽  
Amino Acid ◽  
Crystal Structures ◽  
Hirshfeld Surface ◽  
Water Molecules ◽  
Narrow Channels ◽  
Amino Acid Conjugates ◽  
Graph Set ◽  
Hydrogen Bond Analysis ◽  
Hydrogen Bonded

This amino acid derived (red&blue) π-stacked (green) hydrogen bonded (striped) dimer forms a pcu-net with water molecules in the narrow channels. Four related molecules are also presented and all were subjected to graph set and Hirshfeld surface analyses.

The formation of paracetamol (acetaminophen) adducts with hydrogen-bond acceptors

2002 ◽  
Vol 58 (6) ◽  
pp. 1057-1066 ◽  
Author(s):  
Iain D. H. Oswald ◽  
David R. Allan ◽  
Pamela A. McGregor ◽  
W. D. Samuel Motherwell ◽  
Simon Parsons ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Crystal Structures ◽  
Systematic Study ◽  
Guest Molecule ◽  
Guest Molecules ◽  
Oh Groups ◽  
Stacking Interaction ◽  
Hydrogen Bond Interactions ◽  
Π Stacking Interaction ◽  
Graph Set

The crystal structures of five hemiadducts of paracetamol with 1,4-dioxane, N-methylmorpholine, morpholine, N,N-dimethylpiperazine and piperazine and a related 1:1 adduct of paracetamol with 4,4′-bipyridine are described. All structures are characterized by the formation of chains of paracetamol molecules, which are linked via either OH...O=C interactions [C(9) chains in graph-set notation] or NH...O=C interactions [C(4) chains], depending on the presence or absence of substituent groups on the guest molecule. In all cases except for the morpholine and bipyridine adducts these chains are connected by hydrogen-bond interactions with the guest molecules, which reside on crystallographic inversion centres. In the bipyridine adduct this linkage also involves a π-stacking interaction; in the morpholine adduct it is formed between the OH groups of two opposed paracetamol molecules. Most adducts (that with 4,4′-bipyridine is an exception) decompose on heating to give monoclinic paracetamol. This is the first systematic study of a series of co-crystals containing paracetamol.

Comparison of hydrogen bonds and diverse weak interactions of the nitro group in 2-methyl-4-nitroanilinium nitrate, bisulfate and two hexafluoridosilicates: elementary graph-set approach

2016 ◽  
Vol 72 (6) ◽  
pp. 916-926 ◽  
Author(s):  
Marek Daszkiewicz ◽  
Agnieszka Mielcarek
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Nitro Group ◽  
Weak Interactions ◽  
Gradual Expansion ◽  
Graph Set ◽  
Mathematical Relations ◽  
Elementary Graph ◽  
Bonding Patterns

Crystal structures of (H2m4na)NO3(1), (H2m4na)HSO4(2), (H2m4na)2SiF6(3) and (H2m4na)2SiF6·2H2O (4), where 2m4na = 2-methyl-4-nitroaniline, are presented. Two layers of interactions occur in the structures, N—H...O/F hydrogen bonds and interactions with the nitro group. Although diverse, hydrogen-bonding patterns are compared with each other by means of interrelations among elementary graph-set descriptors and descriptors of hydrogen-bonding patterns. Using mathematical relations, the gradual expansion of the ring patterns was shown in the crystal structures. Parallel and perpendicular arranged nitro groups form weak π(N)NO2...π(O)NO2and π(N)NO2...ONO2interactions, respectively. The πNO2...πringinteraction has an impact to the stabilization of parallel oriented nitro groups. Generally, weak interactions constructed by the nitro group occur in the studied crystals as follows: π(N)NO2...π(O)NO2, πring...πring, C—H...O (1); π(N)NO2...π(O)NO2, π(N)NO2...ONO2(2); π(N)NO2...π(O)NO2, π(N)NO2...ONO2(3); C—H...O (4).

Graph-set analysis of hydrogen-bond patterns: some mathematical concepts

1999 ◽  
Vol 55 (6) ◽  
pp. 1030-1043 ◽  
Author(s):  
J. Grell ◽  
J. Bernstein ◽  
G. Tinhofer
Keyword(s):  
Hydrogen Bond ◽  
Iminodiacetic Acid ◽  
Mathematical Tool ◽  
Mathematical Concepts ◽  
Structural Database ◽  
Graph Set ◽  
Pattern Forming ◽  
Definition Of ◽  
Graph Sets ◽  
Graph Set Analysis

To provide a foundation for further theoretical and software development of the application of graph sets to patterns of hydrogen bonding and other intermolecular interactions a number of mathematical concepts and tools are defined, developed and demonstrated. Following a review of the basic definitions and uses of graph sets, the directional properties of hydrogen bonds are now included in the treatment. The concepts of a constructor graph and covalent distance matrix have been developed to aid in the generation of a qualitative descriptor for the straightforward, consistent and ultimately automatic (with appropriate software) definition of patterns. An additional mathematical tool, the arrowed T-labeling, has been developed to deal with situations in which pattern-forming moieties are located on crystallographic special positions. To demonstrate the utility and various features of these concepts they are applied in detail to two particular structures, polymorphic iminodiacetic acid [N-(carboxymethyl)glycine] and trans-tetraamminedinitrocobalt(III) acetate. To facilitate the application and use of graph sets many of these developments have already been incorporated into the software of the Cambridge Structural Database, as described in the accompanying paper.

Halogen bonding directed supramolecular assembly in bromo-substituted trezimides and tennimides

CrystEngComm ◽  
2014 ◽  
Vol 16 (10) ◽  
pp. 1893-1903 ◽  
Author(s):  
Pavle Mocilac ◽  
John F. Gallagher
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Crystal Structures ◽  
Supramolecular Assembly ◽  
Halogen Bonding ◽  
Strong Hydrogen Bond ◽  
Aggregation Process ◽  
Halogen Bonds ◽  
State Aggregation ◽  
Hydrogen Bond Donors

The imide-based trezimide and tennimide macrocycle crystal structures typically aggregate as 1-D chains through C–Br⋯OC/N/π(arene) halogen bonds (withNc≤ 0.90) that dominate the solid-state aggregation process in the absence of classical strong hydrogen bond donors.

Structures and Photochemistry of Inclusion Compounds of 9,10-Dihydro-9,10-ethenoanthracene-11,12-bis(diphenylmethanol)

1997 ◽  
Vol 53 (2) ◽  
pp. 300-305 ◽  
Author(s):  
T. Y. Fu ◽  
J. R. Scheffer ◽  
J. Trotter
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Solid State Reaction ◽  
Inclusion Compounds ◽  
Host Molecule ◽  
Molecular Rearrangement ◽  
Intermolecular Hydrogen Bonds ◽  
Solvent Molecules

Crystal structures have been determined for inclusion complexes of the host molecule 9,10-dihydro-9,10-ethenoanthracene-11,12-bis(diphenylmethanol), with acetone, ethanol and toluene as guest solvent molecules. The host molecule exhibits an intramolecular O--H...O hydrogen bond in each of the complexes, with intermolecular hydrogen bonds to the acetone and ethanol guests. Different photoproducts are obtained from solution and solid-state photolyses; the solid-state reaction involves a relatively small amount of molecular rearrangement, for which a mechanism is proposed.

Notizen: The Crystal Structures of Pyridinium Chloride Revisited: Evidence for Extensive C–H ••• Cl Hydrogen-Bond Interactions

1993 ◽  
Vol 48 (7) ◽  
pp. 1023-1026 ◽  
Author(s):  
Christer B. Aakeröy ◽  
Kenneth R. Seddon
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Pyridinium Chloride ◽  
Structural Role ◽  
Hydrogen Bond Interactions

A reinvestigation of the previously determined structures of two polymorphs of pyridinium chloride shows that both polymorphs contain several aromatic C– H-H···Cl hydrogen-bond interactions. These hydrogen bonds, hitherto unrecognized, may play a significant structural role, both in solution and in the solid-state.

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