Cocrystals of 3,5-Dimethyl-1H-pyrazole and Salicylic Acid:  Controlled Formation of Trimers via O−H···N Hydrogen Bonds†

2007 ◽  
Vol 7 (6) ◽  
pp. 1176-1184 ◽  
Author(s):  
Concepción López ◽  
Rosa M. Claramunt ◽  
María Ángeles García ◽  
Elena Pinilla ◽  
M. Rosario Torres ◽  
...  
Keyword(s):  
Salicylic Acid ◽  
Hydrogen Bonds

Intra- and intermolecular interactions in small bioactive molecules: cooperative features from experimental and theoretical charge-density analysis

2006 ◽  
Vol 62 (4) ◽  
pp. 612-626 ◽  
Author(s):  
Parthapratim Munshi ◽  
Tayur N. Guru Row
Keyword(s):  
Salicylic Acid ◽  
Hydrogen Bonds ◽  
Intermolecular Interactions ◽  
Density Functional ◽  
Theoretical Calculations ◽  
Topological Analysis ◽  
Van Der Waals Interactions ◽  
Bioactive Molecules ◽  
Topological Features ◽  
Weak Intermolecular Interactions

The topological features of the charge densities, ρ(r), of three bioactive molecules, 2-thiouracil [2,3-dihydro-2-thioxopyrimidin-4(1H)-one], cytosine [4-aminopyrimidin-2(1H)-one] monohydrate and salicylic acid (2-hydroxybenzoic acid), have been determined from high-resolution X-ray diffraction data at 90 K. The corresponding results are compared with the periodic theoretical calculations, based on theoretical structure factors, performed using DFT (density-functional theory) at the B3LYP/6-31G** level. The molecules pack in the crystal lattices via weak intermolecular interactions as well as strong hydrogen bonds. All the chemical bonds, including the intra- and intermolecular interactions in all three compounds, have been quantitatively described by topological analysis based on Bader's quantum theory of `Atoms In Molecules'. The roles of interactions such as C—H...O, C—H...S, C—H...π and π...π have been investigated quantitatively in the presence of strong hydrogen bonds such as O—H...O, N—H...O and N—H...S, based on the criteria proposed by Koch and Popelier to characterize hydrogen bonds and van der Waals interactions. The features of weak intermolecular interactions, such as S...S in 2-thiouracil, the hydrogen bonds generated from the water molecule in cytosine monohydrate and the formation of the dimer via strong hydrogen bonds in salicylic acid, are highlighted on a quantum basis. Three-dimensional electrostatic potentials over the molecular surfaces emphasize the preferable binding sites in the structure and the interaction features of the atoms in the molecules, which are crucial for drug–receptor recognition.

scholarly journals Crystal structure of 3-bromo-2-hydroxybenzoic acid

2015 ◽  
Vol 71 (5) ◽  
pp. 531-535 ◽  
Author(s):  
Gerhard Laus ◽  
Volker Kahlenberg ◽  
Thomas Gelbrich ◽  
Sven Nerdinger ◽  
Herwig Schottenberger
Keyword(s):  
Crystal Structure ◽  
Salicylic Acid ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Title Compound ◽  
Hydroxybenzoic Acid ◽  
Compound C ◽  
Derivatives Of ◽  
Centrosymmetric Dimers ◽  
Ring Motif

Mutual carboxyl–carboxyl O—H...O hydrogen bonds link the molecules of the title compound, C7H5BrO3, into centrosymmetric dimers which display a centralR22(8) ring motif. In addition, there is an intramolecular hydroxyl–carboxyl O—H...O interaction present. A comparison with the crystal structures of 59 other substituted derivatives of salicylic acid shows that both the centrosymmetric carboxyl–carboxyl O—H...O dimer and the stacking mode of molecules along the shortaaxis observed in the title structure are frequent packing motifs in this set.

scholarly journals 4-[Bis(4-fluorophenyl)methyl]piperazin-1-ium 2-hydroxybenzoate 2-hydroxybenzoic acid monosolvate

2012 ◽  
Vol 68 (4) ◽  
pp. o1180-o1180 ◽  
Author(s):  
A. S. Dayananda ◽  
H. S. Yathirajan ◽  
Ulrich Flörke
Keyword(s):  
Hydrogen Bond ◽  
Salicylic Acid ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Crystal Packing ◽  
Three Dimensional ◽  
Hydroxybenzoic Acid ◽  
Acid Molecule ◽  
Compound C ◽  
Dimensional Network

The title compound, C17H19F2N2+·C7H5O3−·C7H6O3, is a co-crystal from 4-[bis(4-fluorophenyl)methyl]piperazin-1-ium, salicylate anion and salicylic acid in a 1:1:1 ratio. In addition to an intramolecular O—H...O hydrogen bond, the crystal packing shows hydrogen bonds between the piperazinium cation and salicylate anion (N—H...O), as well as between the salicylic acid molecule and anion (O—H...O), giving rise to a three-dimensional network.

Hydrogen bonds in 1:1 complex of piperidine-3-carboxylic acid with salicylic acid

2009 ◽  
Vol 920 (1-3) ◽  
pp. 68-74 ◽  
Author(s):  
Elżbieta Bartoszak-Adamska ◽  
Zofia Dega-Szafran ◽  
Magdalena Krociak ◽  
Mariusz Jaskolski ◽  
Mirosław Szafran
Keyword(s):  
Salicylic Acid ◽  
Carboxylic Acid ◽  
Hydrogen Bonds

scholarly journals Crystal structure of 2,5-dimethylanilinium salicylate

2015 ◽  
Vol 71 (9) ◽  
pp. o643-o644 ◽  
Author(s):  
A. Mani ◽  
P. Praveen Kumar ◽  
G. Chakkaravarthi
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Salicylic Acid ◽  
Hydrogen Bonds ◽  
Transfer Reaction ◽  
Three Dimensional ◽  
Proton Transfer Reaction ◽  
Dimensional Network ◽  
Centroid Distance ◽  
Molecular Salt

The title molecular salt, C8H12N+·C7H5O3−arose from the proton-transfer reaction between 2,5-xylidine and salicylic acid. In the anion, the dihedral angle between the planes of the aromatic ring and the –CO2−group is 11.08 (8)°; this near planarity is consolidated by an intramolecular O—H...O hydrogen bond. In the crystal, the components are connected by N—H...O hydrogen bonds, with all three O atoms in the anion acting as acceptors; the result is a [100] chain. The structure also features weak C—H...O bonds and aromatic π–π stacking [centroid-to-centroid distance = 3.7416 (10) Å] interactions, which lead to a three-dimensional network.

Competing Interactions: Evolution of Inter and Intramolecular Hydrogen Bonds in Salicylic Acid at High Pressures

2019 ◽  
Vol 124 (2) ◽  
pp. 373-379
Author(s):  
Ajay K. Mishra ◽  
Chitra Murli ◽  
K. K. Pandey ◽  
T. Sakuntala ◽  
Himanshu Kumar Poswal ◽  
...  
Keyword(s):  
Salicylic Acid ◽  
Hydrogen Bonds ◽  
High Pressures ◽  
Competing Interactions ◽  
Intramolecular Hydrogen Bonds ◽  
Intramolecular Hydrogen
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