Interaction of indole derivatives with biologically important aromatic compounds. Part 22. Importance of simultaneous co-operation of hydrogen-bond pairing and stacking interactions for recognition of guanine base by a peptide: X-ray crystal analysis of 7-methylguanosine-5′-phosphate–tryptophanylglutamic acid complex

1991 ◽  
pp. 1847-1853 ◽  
Author(s):  
Toshimasa Ishida ◽  
Hiromi Iyo ◽  
Hitoshi Ueda ◽  
Mitsunobu Doi ◽  
Masatoshi Inoue ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Aromatic Compounds ◽  
Stacking Interactions ◽  
Indole Derivatives ◽  
Acid Complex ◽  
X Ray ◽  
Guanine Base

scholarly journals Synthetic Studies on Potent Marine Drugs: Synthesis and the Crystal Structure of 6-tert-butyl-4-phenyl-4H-chromene-2-carboxylic Acid

2013 ◽  
Vol 2013 ◽  
pp. 1-9 ◽  
Author(s):  
Hui-Jing Li ◽  
Jun-Li Wang ◽  
Rui Wang ◽  
Dong-Hui Luo ◽  
Yan-Chao Wu
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Methyl Ester ◽  
Crystallographic Analysis ◽  
Antitumor Antibiotic ◽  
Stacking Interactions ◽  
X Ray ◽  
Structural Activity Relationship ◽  
Derivatives Of

4H-Chromene-2-carboxylic acid ester derivatives of renieramycin M might be of use for the structural-activity relationship studies of antitumor antibiotic tetrahydroisoquinoline natural products. Accordingly, 6-tert-butyl-4-phenyl-4H-chromene-2-carboxylic acid, one key intermediate, was synthesized via the condensation of (3E)-2-oxo-4-phenylbut-3-enoate methyl ester with 4-tert-butylphenol in the presence of AuCl3/3AgOTf (5 mol%), followed by cyclodehydration and aqueous hydrolysis. The product was unambiguously shown to the 4H-chromene-2-carboxylic acid by spectroscopy and X-ray crystallographic analysis. A packing diagram of the crystal structure shows that aromaticπ-stacking interactions and O–H⋯O hydrogen bond stabilize the structure in the solid.

Positional isomeric effect on the crystallization of chlorine-substitutedN-phenyl-2-phthalimidoethanesulfonamide derivatives

2015 ◽  
Vol 71 (9) ◽  
pp. 839-843 ◽  
Author(s):  
Serap Köktaş Koca ◽  
Resul Sevinçek ◽  
Özlem Akgül ◽  
Muhittin Aygün
Keyword(s):  
Hydrogen Bond ◽  
Biological Activities ◽  
Intermolecular Hydrogen Bond ◽  
Stacking Interactions ◽  
X Ray ◽  
Space Groups ◽  
X Ray Crystallography ◽  
Hydrogen Bond Interactions ◽  
Benzene Rings ◽  
Isomeric Effect

Theortho-,para- andmeta-chloro-substitutedN-chlorophenyl-2-phthalimidoethanesulfonamide derivatives, C16H13ClN2O4S, have been structurally characterized by single-crystal X-ray crystallography.N-(2-Chlorophenyl)-2-phthalimidoethanesulfonamide, (I), has orthorhombic (P212121) symmetry,N-(4-chlorophenyl)-2-phthalimidoethanesulfonamide, (II), has triclinic (P\overline{1}) symmetry andN-(3-chlorophenyl)-2-phthalimidoethanesulfonamide, (III), has monoclinic (P21/c) symmetry. The molecules of (I)–(III) are regioisomers which have crystallized in different space groups as a result of the differing intra- and intermolecular hydrogen-bond interactions which are present in each structure. Compounds (I) and (II) are stabilized by N—H...O and C—H...O hydrogen bonds, while (III) is stabilized by N—H...O, C—H...O and C—H...Cl hydrogen-bond interactions. The structure of (II) also displays π–π stacking interactions between the isoindole and benzene rings. All three structures are of interest with respect to their biological activities and have been studied as part of a programme to develop anticonvulsant drugs for the treatment of epilepsy.

Experimental charge density of an L-phenylalanine formic acid complex with a short hydrogen bond determined at 25 K

2006 ◽  
Vol 221 (9) ◽  
Author(s):  
Stefan Mebs ◽  
Marc Messerschmidt ◽  
Peter Luger
Keyword(s):  
Hydrogen Bond ◽  
High Resolution ◽  
Formic Acid ◽  
Charge Density ◽  
Topological Properties ◽  
Acid Complex ◽  
Data Set ◽  
X Ray ◽  
Short Hydrogen Bond ◽  
Experimental Charge Density

AbstractThe experimental charge density and related atomic and bond topological properties of an L-phenylalanine formic acid complex were derived from a high resolution X-ray data set (sin θ/λ = 1.18 Å

scholarly journals Synthesis, crystal structure, Hirschfeld surface analysis and biological activity prediction of N-(dimethoxyphosphoryl)-1-methylpyridinium-4-carboximidate

2021 ◽  
pp. 137-144
Author(s):  
V.A. Trush ◽  
◽  
N.S. Kariaka ◽  
I.S. Konovalova ◽  
S.V. Shishkina ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Biological Activity ◽  
Computer Program ◽  
31P Nmr ◽  
Crystallographic Axis ◽  
Stacking Interactions ◽  
Activity Prediction ◽  
X Ray ◽  
Crystallographic Axes

N-(dimethoxyphosphoryl)-1-methylpyridinium-4-carboximidate, a new carbacylamidophosphate-type compound, was synthesized and characterized by means of IR, 1H and 31P NMR and UV-Vis spectroscopies and X-ray analysis. The molecule of the synthesized compound has triclinic (P-1) symmetry, displays monomeric motif in crystal and crystalizes as solvate containing methanol molecule, which is connected to carbacylamidophosphate molecule through O(2)H(5A)–O(5) hydrogen bond. Through – stacking interactions, the molecules of the synthesized compound are linked in the chain along the a crystallographic axis. Several other intermolecular bonds connect these chains along b and c crystallographic axes. The intermolecular interactions with HH and OH contacts prevail in the crystalline structure of N-(dimethoxyphosphoryl)-1-methylpyridinium-4-carboximidate, the contribution of planar stacking CC contacts being equal to 4.1%. The synthesized compound was found to be well soluble in water. By using computer program PASS, we established that the synthesized substance is likely can exhibit 18 types of biological activity in experiment.

Self-Recognizing π-π Stacking Interactions Designed for the Generation of Ultrastable Mesoporous Hydrogen-Bonded Organic Frameworks

2019 ◽  
Author(s):  
KAIKAI MA ◽  
Peng Li ◽  
John Xin ◽  
Yongwei Chen ◽  
Zhijie Chen ◽  
...  
Keyword(s):  
Pore Size ◽  
Fiber Composite ◽  
Aqueous Media ◽  
Stacking Interactions ◽  
Mustard Gas ◽  
X Ray Diffraction ◽  
X Ray ◽  
Expansion Strategy ◽  
Π Stacking ◽  
Hydrogen Bonded

Creating crystalline porous materials with large pores is typically challenging due to undesired interpen-etration, staggered stacking, or weakened framework stability. Here, we report a pore size expansion strategy by self-recognizing π-π stacking interactions in a series of two-dimensional (2D) hydrogen–bonded organic frameworks (HOFs), HOF-10x (x=0,1,2), self-assembled from pyrene-based tectons with systematic elongation of π-conjugated molecular arms. This strategy successfully avoids interpene-tration or staggered stacking and expands the pore size of HOF materials to access mesoporous HOF-102, which features a surface area of ~ 2,500 m2/g and the largest pore volume (1.3 cm3/g) to date among all reported HOFs. More importantly, HOF-102 shows significantly enhanced thermal and chemical stability as evidenced by powder x-ray diffraction and N2 isotherms after treatments in chal-lenging conditions. Such stability enables the adsorption of dyes and cytochrome c from aqueous media by HOF-102 and affords a processible HOF-102/fiber composite for the efficient photochemical detox-ification of a mustard gas simulant.

X-ray Crystal Structure of Gallium Tris- (8-hydroxyquinoline):  Intermolecular π−π Stacking Interactions in the Solid State

1999 ◽  
Vol 11 (3) ◽  
pp. 530-532 ◽  
Author(s):  
Yue Wang ◽  
Weixing Zhang ◽  
Yanqin Li ◽  
Ling Ye ◽  
Guangdi Yang
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Stacking Interactions ◽  
X Ray ◽  
Π Stacking

scholarly journals Isomeric 4,2′:6′,4″- and 3,2′:6′,3″-Terpyridines with Isomeric 4′-Trifluoromethylphenyl Substituents: Effects on the Assembly of Coordination Polymers with [Cu(hfacac)2] (Hhfacac = Hexafluoropentane-2,4-dione)

Inorganics ◽  
2021 ◽  
Vol 9 (7) ◽  
pp. 54
Author(s):  
Giacomo Manfroni ◽  
Simona S. Capomolla ◽  
Alessandro Prescimone ◽  
Edwin C. Constable ◽  
Catherine E. Housecroft
Keyword(s):  
Coordination Polymers ◽  
Metal Binding ◽  
Polymer Chains ◽  
Stacking Interactions ◽  
X Ray Diffraction ◽  
Preparative Scale ◽  
X Ray ◽  
Single Crystal Structures ◽  
Π Stacking ◽  
Packing Interactions

The isomers 4′-(4-(trifluoromethyl)phenyl)-4,2′:6′,4″-terpyridine (1), 4′-(3-(trifluoromethyl)phenyl)-4,2′:6′,4″-terpyridine (2), 4′-(4-(trifluoromethyl)phenyl)-3,2′:6′,3″-terpyridine (3), and 4′-(3-(trifluoromethyl)phenyl)-3,2′:6′,3″-terpyridine (4) have been prepared and characterized. The single crystal structures of 1 and 2 were determined. The 1D-polymers [Cu2(hfacac)4(1)2]n.2nC6H4Cl2 (Hhfacac = 1,1,1,5,5,5-hexafluoropentane-2,4-dione), [Cu(hfacac)2(2)]n.2nC6H5Me, [Cu2(hfacac)4(3)2]n.nC6H4Cl2, [Cu2(hfacac)4(3)2]n.nC6H5Cl, and [Cu(hfacac)2(4)]n.nC6H5Cl have been formed by reactions of 1, 2, 3 and 4 with [Cu(hfacac)2].H2O under conditions of crystal growth by layering and four of these coordination polymers have been formed on a preparative scale. [Cu2(hfacac)4(1)2]n.2nC6H4Cl2 and [Cu(hfacac)2(2)]n.2nC6H5Me are zig-zag chains and the different substitution position of the CF3 group in 1 and 2 does not affect this motif. Packing of the polymer chains is governed mainly by C–F...F–C contacts, and there are no inter-polymer π-stacking interactions. The conformation of the 3,2′:6′,3″-tpy unit in [Cu2(hfacac)4(3)2]n.nC6H4Cl2 and [Cu(hfacac)2(4)]n.nC6H5Cl differs, leading to different structural motifs in the 1D-polymer backbones. In [Cu(hfacac)2(4)]n.nC6H5Cl, the peripheral 3-CF3C6H4 unit is accommodated in a pocket between two {Cu(hfacac)2} units and engages in four C–Hphenyl...F–Chfacac contacts which lock the phenylpyridine unit in a near planar conformation. In [Cu2(hfacac)4(3)2]n.nC6H4Cl2 and [Cu(hfacac)2(4)]n.nC6H5Cl, π-stacking interactions between 4′-trifluoromethylphenyl-3,2′:6′,3″-tpy domains are key packing interactions, and this contrasts with the packing of polymers incorporating 1 and 2. We use powder X-ray diffraction to demonstrate that the assemblies of the coordination polymers are reproducible, and that a switch from a 4,2′:6′,4″- to 3,2′:6′,3″-tpy metal-binding unit is accompanied by a change from dominant C–F...F–C and C–F...H–C contacts to π-stacking of arene domains between ligands 3 or 4.

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