Supramolecular Chemistry of Folic Acid — Experimental and Computational Investigation

Supramolecular chemistry of folic acid is studied and revealed by exploring its assembly and disassembly process in a liquid–liquid interface. Experimental and computational studies are conducted to understand the interfacial interactions of folic acid in a oil-in-water interface by investigating the role of folic acid’s critical aggregation concentration (CAC), molecular arrangement, and intermolecular interactions at the molecular level. The folic acid’s CAC, determined from the concentration-dependent UV–vis absorption spectra in water/methanol solvent system, is found to be 2.72[Formula: see text][Formula: see text]M. The sigmoidal behavior of folic acid’s maximum absorbances with respect to different folic acid concentrations reveals the nature of the self-assembly dynamics and aggregative assemblies’ formation by three signature phases, in which CAC lies in the second phase — the growth phase. The computational studies reveal the intermolecular interactions and molecular orientation of folic acid molecules. They interact each other via H2-bonding between carboxylic acid groups in two glutamate units and two amine groups in pteridine units and [Formula: see text]–[Formula: see text] interactions between pteridine units and phenyl units, orienting two units in a parallel stacked arrangement. Correlating the computed intermolecular interactions and structural orientation of folic acid with its solid-state crystal packing structure has provided strong evidence supporting its supramolecular chemistry and assembly dynamics to make nanoassemblies in a liquid–liquid interface.

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Synthesis of a New Series of Organic Solid-State Near-Infrared Emitters: The Role of Crystal Packing and Weak Intermolecular Interactions and Application in Latent Fingerprint Detection

Crystal Growth & Design ◽

10.1021/acs.cgd.0c01392 ◽

2021 ◽

Vol 21 (2) ◽

pp. 1062-1076

Author(s):

Ranjit Singh ◽

Abhishek Kumar Gupta ◽

Chullikkattil P. Pradeep

Keyword(s):

Solid State ◽

Intermolecular Interactions ◽

Near Infrared ◽

Crystal Packing ◽

Latent Fingerprint ◽

Weak Intermolecular Interactions ◽

Organic Solid ◽

Infrared Emitters ◽

Fingerprint Detection

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Convenient Access to Functionalized Non-Symmetrical Atropisomeric 4,4′-Bipyridines

Compounds ◽

10.3390/compounds1020006 ◽

2021 ◽

Vol 1 (2) ◽

pp. 58-74

Author(s):

Emmanuel Aubert ◽

Emmanuel Wenger ◽

Paola Peluso ◽

Victor Mamane

Keyword(s):

Solid State ◽

Intermolecular Interactions ◽

Medicinal Chemistry ◽

Crystal Packing ◽

Cross Coupling ◽

Coupling Reactions ◽

Halogen Bonds ◽

Cross Coupling Reactions ◽

Cyano Groups ◽

Post Functionalization

Non-symmetrical chiral 4,4′-bipyridines have recently found interest in organocatalysis and medicinal chemistry. In this regard, the development of efficient methods for their synthesis is highly desirable. Herein, a series of non-symmetrical atropisomeric polyhalogenated 4,4′-bipyridines were prepared and further functionalized by using cross-coupling reactions. The desymmetrization step is based on the N-oxidation of one of the two pyridine rings of the 4,4′-bipyridine skeleton. The main advantage of this methodology is the possible post-functionalization of the pyridine N-oxide, allowing selective introduction of chlorine, bromine or cyano groups in 2- and 2′-postions of the chiral atropisomeric 4,4′-bipyridines. The crystal packing in the solid state of some newly prepared derivatives was analyzed and revealed the importance of halogen bonds in intermolecular interactions.

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Intermolecular Interactions at the Silica–Liquid Interface Modulate the Fermi Resonance Coupling in Surface Methanol

The Journal of Physical Chemistry Letters ◽

10.1021/acs.jpclett.1c01015 ◽

2021 ◽

pp. 5695-5702

Author(s):

Thomas T. Bui ◽

Luis A. Colón ◽

Luis Velarde

Keyword(s):

Intermolecular Interactions ◽

Liquid Interface ◽

Fermi Resonance ◽

Resonance Coupling

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4-Acetylpiperazinium picrate

Acta Crystallographica Section E Structure Reports Online ◽

10.1107/s1600536814011726 ◽

2014 ◽

Vol 70 (6) ◽

pp. o717-o718 ◽

Cited By ~ 1

Author(s):

Channappa N. Kavitha ◽

Manpreet Kaur ◽

Jerry P. Jasinski ◽

Hemmige S. Yathirajan

Keyword(s):

Hydrogen Bonds ◽

Benzene Ring ◽

Intermolecular Interactions ◽

Crystal Packing ◽

Chair Conformation ◽

Centroid Distance ◽

Sheet Structure ◽

Benzene Rings ◽

Π Stacking Interaction ◽

The Mean

In the title salt, C6H13N2O+·C6H2N3O7−(systematic name: 4-acetylpiperazin-1-ium 2,4,6-trinitrophenolate), the piperazin-1-ium ring has a slightly distorted chair conformation. In the picrate anion, the mean planes of the twoo-NO2andp-NO2groups are twisted with respect to the benzene ring by 15.0 (2), 68.9 (4) and 4.4 (3)°, respectively. In the crystal, N—H...O hydrogen bonds are observed, linking the ions into an infinite chain along [010]. In addition, weak cation–anion C—H...O intermolecular interactions and a weak π–π stacking interaction between the benzene rings of the anions, with an inter-centroid distance of 3.771 (8) Å, help to stabilize the crystal packing, giving an overall sheet structure lying parallel to (100). Disorder was modelled for one of the O atoms in one of theo-NO2groups over two sites with an occupancy ratio of 0.57 (6):0.43 (6).

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Substituent and Solvent Effects on Intermolecular Interactions in Crystals of N-Acylhydrazone Derivatives: Single-Crystal X-ray, Solid-State NMR, and Computational Studies

Crystal Growth & Design ◽

10.1021/cg401866x ◽

2014 ◽

Vol 14 (5) ◽

pp. 2263-2281 ◽

Cited By ~ 17

Author(s):

Liliana Mazur ◽

Katarzyna N. Jarzembska ◽

Radosław Kamiński ◽

Krzysztof Woźniak ◽

Edyta Pindelska ◽

...

Keyword(s):

Solid State ◽

Single Crystal ◽

Intermolecular Interactions ◽

Solvent Effects ◽

Solid State Nmr ◽

Computational Studies ◽

X Ray

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(Z)-4-n-Butyl-2-(4-chlorobenzylidene)-2H-1,4-benzothiazin-3(4H)-one

IUCrData ◽

10.1107/s2414314617008707 ◽

2017 ◽

Vol 2 (6) ◽

Author(s):

Mohamed Ellouz ◽

Nada Kheira Sebbar ◽

Younes Ouzidan ◽

Manpreet Kaur ◽

El Mokhtar Essassi ◽

...

Keyword(s):

Hydrogen Bond ◽

Dihedral Angle ◽

Intermolecular Interactions ◽

Title Compound ◽

Crystal Packing ◽

Boat Conformation ◽

Compound C ◽

Phenyl Rings

In the title compound, C19H18ClNOS, the thiazin-3-one ring adopts a slightly distorted screw-boat conformation. An intramolecular C—H...S hydrogen bond encloses anS(6) ring and affects the overall conformation of the molecule. The dihedral angle between the two phenyl rings is 52.3 (2)°. In the crystal, weak C—H...O intermolecular interactions stabilize the crystal packing.

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Salt formation, hydrogen-bonding patterns and supramolecular architectures of acridine with salicylic and hippuric acid molecules

Acta Crystallographica Section C Structural Chemistry ◽

10.1107/s2053229621011189 ◽

2021 ◽

Vol 77 (12) ◽

Author(s):

Suresh Suganya ◽

Kandasamy Saravanan ◽

Ramakrishnan Jaganathan ◽

Poomani Kumaradhas

Keyword(s):

Hydrogen Bonding ◽

Intermolecular Interactions ◽

Hippuric Acid ◽

Crystal Packing ◽

Noncovalent Interactions ◽

Salt Formation ◽

Aminosalicylic Acid ◽

Dispersion Interactions ◽

Supramolecular Architectures ◽

Quantitative Contributions

The intermolecular interactions and salt formation of acridine with 4-aminosalicylic acid, 5-chlorosalicylic acid and hippuric acid were investigated. The salts obtained were acridin-1-ium 4-aminosalicylate (4-amino-2-hydroxybenzoate), C13H10N+·C7H6NO3 − (I), acridin-1-ium 5-chlorosalicylate (5-chloro-2-hydroxybenzoate), C13H10N+·C7H4ClO3 − (II), and acridin-1-ium hippurate (2-benzamidoacetate) monohydrate, C13H10N+·C9H8NO3 −·H2O (III). Acridine is involved in strong intermolecular interactions with the hydroxy group of the three acids, enabling it to form supramolecular assemblies. Hirshfeld surfaces, fingerprint plots and enrichment ratios were generated and investigated, and the intermolecular interactions were analyzed, revealing their quantitative contributions in the crystal packing of salts I, II and III. A quantum theory of atoms in molecules (QTAIM) analysis shows the charge–density distribution of the intermolecular interactions. The isosurfaces of the noncovalent interactions were studied, which allows visualization of where the hydrogen-bonding and dispersion interactions contribute within the crystal.

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Supramolecular chemistry of helical foldamers at the solid–liquid interface: self-assembled monolayers and anion recognition

Chemical Communications ◽

10.1039/c9cc03851e ◽

2019 ◽

Vol 55 (58) ◽

pp. 8426-8429 ◽

Cited By ~ 5

Author(s):

Catherine Adam ◽

Lara Faour ◽

Valérie Bonnin ◽

Tony Breton ◽

Eric Levillain ◽

...

Keyword(s):

Supramolecular Chemistry ◽

Anion Recognition ◽

Liquid Interface ◽

Self Assembled Monolayers ◽

Guest Binding ◽

Assembled Monolayers ◽

Self Assembled ◽

Solid Liquid Interface ◽

Solid Liquid

Helical foldamers were incorporated in self-assembled monolayers that successfully transduce host–guest binding events.

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Synthesis, growth, structure and characterization of molybdenum zinc thiourea complex crystals

Acta Crystallographica Section B Structural Science Crystal Engineering and Materials ◽

10.1107/s2052520615005922 ◽

2015 ◽

Vol 71 (3) ◽

pp. 285-292 ◽

Cited By ~ 1

Author(s):

M. Rajasekar ◽

K. Muthu ◽

A. Aditya Prasad ◽

R. Agilandeshwari ◽

SP Meenakshisundaram

Keyword(s):

Single Crystal ◽

Diffraction Analysis ◽

Intermolecular Interactions ◽

Crystal Packing ◽

Second Harmonic ◽

Morphological Changes ◽

Strong Interactions ◽

X Ray Diffraction ◽

X Ray ◽

Cell Parameters

Single crystals of molybdenum-incorporated tris(thiourea)zinc(II) sulfate (MoZTS) are grown by the slow evaporation solution growth technique. Crystal composition as determined by single-crystal X-ray diffraction analysis reveals that it belongs to the orthorhombic system with space groupPca21and cell parametersa= 11.153 (2),b= 7.7691 (14),c= 15.408 (3) Å,V= 1335.14 (4) Å3andZ= 4. The surface morphological changes are studied by scanning electron microscopy. The vibrational patterns in FT–IR are used to identify the functional group and TGA/DTA (thermogravimetric analysis/differential thermal analysis) indicates the stability of the material. The structure and the crystallinity of the material were confirmed by powder X-ray diffraction analysis and the simulated X-ray diffraction (XRD) closely matches the experimental one with varied intensity patterns. The band gap energy is estimated using diffuse reflectance data by the application of the Kubelka–Munk algorithm. The relative second harmonic generation (SHG) efficiency measurements reveal that MoZTS has an efficiency comparable to that of tris(thiourea)zinc(II) sulfate (ZTS). Hirshfeld surfaces were derived using single-crystal X-ray diffraction data. Investigation of the intermolecular interactions and crystal packingviaHirshfeld surface analysis reveal that the close contacts are associated with strong interactions. Intermolecular interactions as revealed by the fingerprint plot and close packing could be the possible reasons for facile charge transfer leading to SHG activity.

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