C–H⋯O and other weak hydrogen bonds. From crystal engineering to virtual screening

2005 ◽  
pp. 2995 ◽  
Author(s):  
Gautam R. Desiraju
Keyword(s):  
Virtual Screening ◽  
Hydrogen Bonds ◽  
Crystal Engineering ◽  
Weak Hydrogen Bonds

Crystal Engineering of a New Layered Polyiodide Using 1,9-Diammoniononane as a Flexible Template Cation

2004 ◽  
Vol 59 (10) ◽  
pp. 1114-1117 ◽  
Author(s):  
Guido J. Reiß ◽  
Judith S. Engel
Keyword(s):  
Thermal Analysis ◽  
Hydrogen Bonding ◽  
Raman Spectrum ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Crystal Engineering ◽  
Title Compound ◽  
State Structure ◽  
Cooperative Phenomenon ◽  
Weak Hydrogen Bonds

AbstractThe reaction of 1,9-diaminononane with hydroiodic acid in the presence of iodine gave a compound best described as 1,9-diammoniononane bis-triiodide iodine, (H3N-(CH2)9-NH3)[I3]2 · I2. The structure is built from two crystallographically independent I3− anions, which are connected via secondary I···I interactions to the iodine molecules, and the 1,9-diammonioalkane cations are connected via weak hydrogen bonds to neighbouring iodine atoms. By a cooperative phenomenon, the shape and the functionality of the cation lead to a solid state structure that includes a polyiodide substructure with the formula 2∞[I8]2− or 2∞[I3 · I2 · I3]2−, is best described as a brick-shaped layered array. Its rectangular pores fit excellently with the hydrogen bonding functionality as well as with the conformational needs of the 1,9-diammoniononane template. The Raman spectrum shows typical bands of coordinated triiodide anions and iodine molecules. The thermal analysis (DSC/TG) of the title compound indicates decomposition at temperatures above 210°C.

Crystal engineering in the gem-alkynol family; synthon repetitivity and topological similarity in diphenylethynylmethanols: structures that lack O—H...O hydrogen bonds

2000 ◽  
Vol 56 (6) ◽  
pp. 1071-1079 ◽  
Author(s):  
Clair Bilton ◽  
Judith A. K. Howard ◽  
N. N. L. Madhavi ◽  
Ashwini Nangia ◽  
Gautam R. Desiraju ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Engineering ◽  
Triple Bond ◽  
Structural Organization ◽  
X Ray Diffraction ◽  
Acta Cryst ◽  
X Ray ◽  
Topological Similarity ◽  
Weak Hydrogen Bonds ◽  
Derivatives Of

The structures of four para-substituted derivatives of diphenylethynylmethanol have been determined [ditolylethynylmethanol, di(4-chlorophenyl)ethynylmethanol, di(4-bromophenyl)ethynylmethanol and bis(4,4′-biphenylyl)ethynylmethanol]. The dimethyl, dichloro, dibromo and diphenyl compounds have been analysed using X-ray diffraction at 150 K, and the dichloro compound has also been studied using neutron diffraction at 150 K. In common with the parent diphenylethynylmethanol [Garcia, Ramos, Rodriguez & Fronczek (1995). Acta Cryst. C51, 2674–2676], all four derivatives fail to form the expected strong O—H...O hydrogen bonds due to steric hindrance. Instead, the supramolecular structural organization in this family of gem-alkynols is mediated by a variety of weaker interactions. The two most acidic protons, O—H and C[triple-bond]C—H, participate in weak hydrogen bonds to π-acceptors, forming synthons that stabilize all five structures. These primary interactions are reinforced by a variety of other weak hydrogen bonds involving C—H donors and the hydroxy-O as an acceptor, and by halogen...halogen interactions in the dichloro and dibromo compounds.

Raman spectroscopy of weak hydrogen bonds in the liquid phase

1978 ◽  
Vol 47 ◽  
pp. 285-290 ◽  
Author(s):  
J.P. Perchard ◽  
C. Perchard ◽  
A. Burneau ◽  
J. Limouzi
Keyword(s):  
Raman Spectroscopy ◽  
Liquid Phase ◽  
Hydrogen Bonds ◽  
Weak Hydrogen Bonds

scholarly journals Charge density studies on 1:1 co-crystals of ethenzamide and saccharin

2014 ◽  
Vol 70 (a1) ◽  
pp. C964-C964
Author(s):  
Lucy Mapp ◽  
Mateusz Pitak ◽  
Simon Coles ◽  
Srinivasulu Aitipamula
Keyword(s):  
Hydrogen Bonds ◽  
Charge Density ◽  
Crystal Engineering ◽  
Chemical Properties ◽  
Secondary Level ◽  
Crystal Form ◽  
Monoclinic Space Group ◽  
Stoichiometric Ratio ◽  
Distribution Analysis ◽  
Space Group

The study of multi-component crystals, as well as the phenomenon of polymorphism, both have relevance to crystal engineering. Obtaining a specific polymorph is crucial as different polymorphs usually exhibit different physical and chemical properties and often the origin of this behaviour is unknown. This is especially important in the pharmaceutical industry. Herein, we present results of comparative studies of an analgesic drug, ethenzamide and its co-crystals with saccharin. The co-crystalisation of ethenzamide (2-ethoxybenzamide, EA) with saccharin (1,1-dioxo-,1,2-benzothiazol-3-one, SAC) with a 1:1 stoichiometric ratio resulted in two polymorphic forms of the co-crystal. Form I crystallises in the triclinic P-1 space group, whereas form II crystallises in monoclinic space group P21/n. Previous crystal structure analyses on forms I and II revealed that in both polymorphs the primary carboxy-amide-imide heterosynthon is the same, however the secondary level of interactions which extends the hydrogen bond network is different. Form I consists of extended linear tapes via N-H···O hydrogen bonds, whereas form II is composed of stacks of tetrameric motifs including N-H···O hydrogen bonds and C-H···O interactions. These two forms of EA-SAC can be classified as synthon polymorphs at a secondary level of hydrogen bonding [1]. In our approach an accurate, high resolution charge density distribution analysis has been carried out to obtain greater insight into the electronic structures of both types of the EA-SAC co-crystals and relate differences in electronic distribution with their polymorphic behaviour. To describe the nature and role of inter and intra-molecular interactions in a quantitative manner, the Hansen-Coppens formalism [2] and Bader's AIM theory [3] approach have been applied.

Halogen Bonds in Crystal Engineering: Like Hydrogen Bonds yet Different

2014 ◽  
Vol 47 (8) ◽  
pp. 2514-2524 ◽  
Author(s):  
Arijit Mukherjee ◽  
Srinu Tothadi ◽  
Gautam R. Desiraju
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Engineering ◽  
Halogen Bonds
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