Qualitative and quantitative analysis of intermolecular interactions in xanthenedione derivatives

2018 ◽  
Vol 74 (7) ◽  
pp. 830-838
Author(s):  
Gayathri Purushothaman ◽  
Vijay Thiruvenkatam
Keyword(s):  
Intermolecular Interactions ◽  
Acetylcholinesterase Inhibitors ◽  
Lattice Energy ◽  
Boat Conformation ◽  
Qualitative And Quantitative Analysis ◽  
Structural Conformation ◽  
Hirshfeld Analysis ◽  
Conformational Geometry ◽  
Twisted Boat

The existence of intermolecular interactions and the conformational geometry adopted by molecules are related to biological activity. Xanthenedione molecules are promising and emerging antioxidants and acetylcholinesterase inhibitors. To examine the role of different functional groups involved in the intermolecular interactions and conformational geometries adopted in xanthenediones, a series of three substituted xanthenediones have been crystallized [9-(3-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione, C23H26O4, 9-(5-bromo-2-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydro-2H-xanthene-1,8(5H,9H)-dione, C24H27BrO4, and 3,3,6,6-tetramethyl-9-(pyridin-2-yl)-3,4,6,7-tetrahydro-2H-xanthene-1,8(5H,9H)-dione, C22H25NO3] and their intermolecular interactions analyzedviaHirshfeld analysis. The results show that all the derivatives adopt the same structural conformation, where the central ring has a shallow boat conformation and the outer rings have a twisted boat conformation. The intermolecular interactions in the molecules are predominantly O—H...O, C—H...O and π–π interactions. The optimized structures of the derivatives from theoretical B3LYP/6-311G** calculations show a good correlation with the experimental structures. The lattice energy involved in the intermolecular interactions has been explored usingPIXELC.

scholarly journals Molecular Structures Polymorphism the Role of F…F Interactions in Crystal Packing of Fluorinated Tosylates

Crystals ◽  
2019 ◽  
Vol 9 (5) ◽  
pp. 242 ◽  
Author(s):  
Dmitry E. Arkhipov ◽  
Alexander V. Lyubeshkin ◽  
Alexander D. Volodin ◽  
Alexander A. Korlyukov
Keyword(s):  
Intermolecular Interactions ◽  
Crystal Packing ◽  
Lattice Energy ◽  
Molecular Structures ◽  
X Ray Diffraction ◽  
Total Contribution ◽  
X Ray ◽  
Weak Hydrogen Bonds ◽  
Intermolecular Bonding

The peculiarities of interatomic interactions formed by fluorine atoms were studied in four tosylate derivatives p-CH3C6H4OSO2CH2CF2CF3 and p-CH3C6H4OSO2CH2(CF2)nCHF2 (n = 1, 5, 7) using X-ray diffraction and quantum chemical calculations. Compounds p-CH3C6H4OSO2CH2(CF2)nCHF2 (n = 1, 5) were crystallized in several polymorph modifications. Analysis of intermolecular bonding was carried out using QTAIM approach and energy partitioning. All compounds are characterized by crystal packing of similar type and the contribution of intermolecular interactions formed by fluorine atoms to lattice energy is raised along with the increase of their amount. The energy of intra- and intermolecular F…F interactions is varied in range 0.5–13.0 kJ/mol. Total contribution of F…F interactions to lattice energy does not exceed 40%. Crystal structures of studied compounds are stabilized mainly by C-H…O and C-H…F weak hydrogen bonds. The analysis of intermolecular interactions and lattice energies in polymorphs of p-CH3C6H4OSO2CH2(CF2)nCHF2 (n = 1, 5) has shown that most stabilized are characterized by the least contribution of F…F interactions.

scholarly journals Quantitative Lattice Energy Analysis of Intermolecular Interactions in Crystal Structures of Some Benzimidazole Derivatives

2020 ◽  
Vol 5 (1-2) ◽  
pp. 53-62
Author(s):  
Gopal Sharma ◽  
Rajni Kant
Keyword(s):  
Crystal Structures ◽  
Intermolecular Interactions ◽  
Energy Analysis ◽  
Crystal Packing ◽  
Lattice Energy ◽  
Molecular Packing ◽  
Benzimidazole Derivatives ◽  
Intermolecular Hydrogen Bonds ◽  
Centrosymmetric Dimers

The benzimidazole moiety found in a large number of biologically important drugs has not been completely realized as yet in respect of its strength and directionality of its molecular interactions. To understand the role played by the intermolecular interactions in the benzimidazole derivatives, lattice energy of a series of five important molecules has been computed and results accrued thereof have been discussed. Analysis of molecular packing based on the intermolecular interaction energies suggests existence of different molecular pairs that play an important role in the stabilization of the crystal structures. Interaction energy analysis of such motifs reveals that intermolecular interactions of the type N-H…N and C-H…N happen to be the major contributors to the stabilization of molecular packing in the unit cell. N-H…π and C-H…π type edge-to-face stacking interactions also contribute significantly to the stabilization of crystal packing. The pairs of N-H…N intermolecular hydrogen bonds link the molecules into centrosymmetric dimers making a contribution of -14 to -18.52 kcal/mol towards stabilization, whereas C-H…N bonds link the molecules into dimers in the energy range of -2 to -5 kcal/mol. Additionally, the role of π…π interactions has also been investigated in molecular stabilization.

Crystal structure and lattice energetics of 10-methylacridinium halides

2000 ◽  
Vol 53 (8) ◽  
pp. 627 ◽  
Author(s):  
Piotr Storoniak ◽  
Karol Krzyminski ◽  
Pawel Dokurno ◽  
Antoni Konitz ◽  
Jerzy Blazejowski
Keyword(s):  
Crystal Lattice ◽  
Lattice Energy ◽  
Enthalpies Of Formation ◽  
Triclinic Space Group ◽  
X Ray ◽  
Molecular Arrangement ◽  
Van Der Waals Contacts ◽  
Chloride Monohydrate ◽  
Insight Into

The crystal structures of 10-methylacridinium chloride monohydrate, bromide monohydrate and iodide were determined by X-ray analysis. The compounds crystallize in the triclinic space group, P¯1, with 2 molecules in the unit cell. The molecular arrangement in the crystals revealed that hydrogen bonds (in hydrates) and van der Waals contacts play a significant part in intermolecular interactions. To discover their nature, contributions to the crystal lattice energy arising from electrostatic (the most important since the compounds form ionic crystals), dispersive and repulsive interactions were calculated. Enthalpies of formation of the salts, their stability and susceptibility to decomposition could be predicted from a combination of crystal lattice energies with values of other thermochemical characteristics obtained theoretically or taken from the literature. The role of water in the stabilization of the crystal lattice of the hydrates is also explained. The information gathered has given an insight into the features and behaviour of compounds which can be regarded as models of a large group of aromatic quaternary nitrogen salts.

The Role of Intermolecular Interactions in Polyurethane Formation

2020 ◽  
pp. 129-138
Author(s):  
Elena V. Stovbun ◽  
Vera P. Lodygina ◽  
Elmira R. Badamshina ◽  
Valentina A. Grigor’eva ◽  
Irina V. Doronina ◽  
...  
Keyword(s):  
Intermolecular Interactions

Intermolecular interactions in highly concentrated protein solutions upon compression and the role of the solvent

2014 ◽  
Vol 141 (22) ◽  
pp. 22D506 ◽  
Author(s):  
S. Grobelny ◽  
M. Erlkamp ◽  
J. Möller ◽  
M. Tolan ◽  
R. Winter
Keyword(s):  
Intermolecular Interactions ◽  
Protein Solutions

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

IUCrData ◽  
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.

Unconditionally stable indole-derived glass blends having very high photorefractive gain: the role of intermolecular interactions

2008 ◽  
Vol 47 (36) ◽  
pp. 6680 ◽  
Author(s):  
Rocco Angelone ◽  
Francesco Ciardelli ◽  
Arturo Colligiani ◽  
Francesco Greco ◽  
Paolo Masi ◽  
...  
Keyword(s):  
Intermolecular Interactions ◽  
Unconditionally Stable ◽  
Very High

Structural characterization and theoretical calculations of the monohydrate of the 1:2 cocrystal salt formed from acriflavine and 3,5-dinitrobenzoic acid

2021 ◽  
Vol 77 (2) ◽  
pp. 116-122
Author(s):  
Maria Marczak ◽  
Kinga Biereg ◽  
Beata Zadykowicz ◽  
Artur Sikorski
Keyword(s):  
Hydrogen Bonds ◽  
Water Molecule ◽  
Intermolecular Interactions ◽  
Structural Characterization ◽  
Theoretical Calculations ◽  
Lattice Energy ◽  
Monoclinic Space Group ◽  
X Ray Diffraction ◽  
Porous Organic Framework ◽  
Organic Framework

The synthesis and structural characterization of the monohydrated 1:2 cocrystal salt of acriflavine with 3,5-dinitrobenzoic acid [systematic name: 3,6-diamino-10-methylacridin-10-ium 3,5-dinitrobenzoate–3,5-dinitrobenzoic acid–water (1/1/1), C14H14N3 +·C7H3N2O6 −·C7H4N2O6·H2O] are reported. Single-crystal X-ray diffraction measurements show that the title solvated monohydrate salt crystalizes in the monoclinic space group P21 with one acriflavine cation, a 3,5-dinitrobenzoate anion, a 3,5-dinitrobenzoic acid molecule and a water molecule in the asymmetric unit. The neutral and anionic forms of 3,5-dinitrobenzoic acid are linked via O—H...O hydrogen bonds to form a monoanionic dimer. Neighbouring monoanionic dimers of 3,5-dinitrobenzoic acid are linked by nitro–nitro N—O...N and nitro–acid N—O...π intermolecular interactions to produce a porous organic framework. The acriflavine cations are linked with carboxylic acid molecules directly via amine–carboxy N—H...O, amine–nitro N—H...O and acriflavine–carboxy C—H...O hydrogen bonds, and carboxy–acriflavine C—O...π, nitro–acriflavine N—O...π and acriflavine–nitro π–π interactions, or through the water molecule by amino–water N—H...O and water–carboxy O—H...O hydrogen bonds, and are located in the voids of the porous organic framework. The intermolecular interactions were studied using the CrystalExplorer program to provide information about the interaction energies and the dispersion, electrostatic, polarization and repulsion contributions to the lattice energy.

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