Hydrogen Bonding Interactions Between Ions: A Powerful Tool in Molecular Crystal Engineering

2005 ◽  
pp. 1-32 ◽  
Author(s):  
Dario Braga ◽  
Lucia Maini ◽  
Marco Polito ◽  
Fabrizia Grepioni
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Engineering ◽  
Molecular Crystal ◽  
Hydrogen Bonding Interactions

Hydrogen Bonding Interactions Between Ions: A Powerful Tool in Molecular Crystal Engineering

ChemInform ◽  
2004 ◽  
Vol 35 (51) ◽  
Author(s):  
Dario Braga ◽  
Lucia Maini ◽  
Marco Polito ◽  
Fabrizia Grepioni
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Engineering ◽  
Molecular Crystal ◽  
Hydrogen Bonding Interactions

Sulfur as hydrogen-bond acceptor in cocrystals of 2-thio-modified thymine

2018 ◽  
Vol 74 (1) ◽  
pp. 21-30 ◽  
Author(s):  
Wilhelm Maximilian Hützler ◽  
Michael Bolte
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Crystal Engineering ◽  
Rational Design ◽  
Three Dimensional ◽  
Good Reliability ◽  
Hydrogen Bond Acceptor ◽  
Hydrogen Bonding Interactions ◽  
Hydrogen Bonding Site ◽  
Hydrogen Bonded

Doubly and triply hydrogen-bonded supramolecular synthons are of particular interest for the rational design of crystal and cocrystal structures in crystal engineering since they show a high robustness due to their high stability and good reliability. The compound 5-methyl-2-thiouracil (2-thiothymine) contains an ADA hydrogen-bonding site (A = acceptor and D = donor) if the S atom is considered as an acceptor. We report herein the results of cocrystallization experiments with the coformers 2,4-diaminopyrimidine, 2,4-diamino-6-phenyl-1,3,5-triazine, 6-amino-3H-isocytosine and melamine, which contain complementary DAD hydrogen-bonding sites and, therefore, should be capable of forming a mixed ADA–DAD N—H...S/N—H...N/N—H...O synthon (denoted synthon 3s N·S;N·N;N·O), consisting of three different hydrogen bonds with 5-methyl-2-thiouracil. The experiments yielded one cocrystal and five solvated cocrystals, namely 5-methyl-2-thiouracil–2,4-diaminopyrimidine (1/2), C5H6N2OS·2C4H6N4, (I), 5-methyl-2-thiouracil–2,4-diaminopyrimidine–N,N-dimethylformamide (2/2/1), 2C5H6N2OS·2C4H6N4·C3H7NO, (II), 5-methyl-2-thiouracil–2,4-diamino-6-phenyl-1,3,5-triazine–N,N-dimethylformamide (2/2/1), 2C5H6N2OS·2C9H9N5·C3H7NO, (III), 5-methyl-2-thiouracil–6-amino-3H-isocytosine–N,N-dimethylformamide (2/2/1), (IV), 2C5H6N2OS·2C4H6N4O·C3H7NO, (IV), 5-methyl-2-thiouracil–6-amino-3H-isocytosine–N,N-dimethylacetamide (2/2/1), 2C5H6N2OS·2C4H6N4O·C4H9NO, (V), and 5-methyl-2-thiouracil–melamine (3/2), 3C5H6N2OS·2C3H6N6, (VI). Synthon 3s N·S;N·N;N·O was formed in three structures in which two-dimensional hydrogen-bonded networks are observed, while doubly hydrogen-bonded interactions were formed instead in the remaining three cocrystals whereby three-dimensional networks are preferred. As desired, the S atoms are involved in hydrogen-bonding interactions in all six structures, thus illustrating the ability of sulfur to act as a hydrogen-bond acceptor and, therefore, its value for application in crystal engineering.

scholarly journals Crystal engineering: co-crystals of cinnamic acid derivatives with a pyridyl derivative co-crystallizer

2016 ◽  
Vol 72 (1) ◽  
pp. 87-95 ◽  
Author(s):  
Daniel A. Lorenzo ◽  
Sebastian J. K. Forrest ◽  
Hazel A. Sparkes
Keyword(s):  
Hydrogen Bonding ◽  
Diffraction Analysis ◽  
Cinnamic Acid ◽  
Crystal Engineering ◽  
X Ray Diffraction ◽  
Cinnamic Acid Derivative ◽  
Cinnamic Acid Derivatives ◽  
X Ray ◽  
Single Crystal Structures ◽  
Hydrogen Bonding Interactions

A number of hydrogen-bonded co-crystals, consisting of a cinnamic acid derivative and a pyridyl co-crystallizer, have been synthesized and their properties investigated by X-ray diffraction. Samples were prepared by recrystallization or solvent drop grinding oftrans-cinnamic acid (1), 4-methylcinnamic acid (2), 4-methoxy cinnamic acid (3) or 3,4-methoxy cinnamic acid (4), with 4,4-dipyridyl (A),iso-nicotinamide (B) or nicotinamide (C). The X-ray single-crystal structures of seven novel co-crystals, obtained through recrystallization, are examined and the hydrogen-bonding interactions discussed. Consistent hydrogen-bonding motifs were observed for samples prepared when using 4,4-dipyridyl (A) oriso-nicotinamide (B) as the co-crystallizing agent. Powder X-ray diffraction analysis of the samples prepared by solvent drop grinding suggests the formation of ten co-crystals.

Arene-Perfluoroarene-Anion Stacking and Hydrogen Bonding Interactions in Imidazolium Salts for the Crystal Engineering of Polarity

2015 ◽  
Vol 16 (1) ◽  
pp. 174-188 ◽  
Author(s):  
Hanan I. Althagbi ◽  
Alison J. Edwards ◽  
Brian K. Nicholson ◽  
Daniel A. Reason ◽  
Graham C. Saunders ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Engineering ◽  
Imidazolium Salts ◽  
Hydrogen Bonding Interactions

‘Neutralmolekülcomplexe’—Structural Characterization of Some Adducts of Urea and Thiourea with N,N′-Bidentate Aromatic Bases

2003 ◽  
Vol 56 (12) ◽  
pp. 1249 ◽  
Author(s):  
Paul S. Donnelly ◽  
Brian W. Skelton ◽  
Allan H. White
Keyword(s):  
Hydrogen Bonding ◽  
Structural Characterization ◽  
Molecular Crystal ◽  
Neutral Molecule ◽  
Hydrogen Bonding Interactions

Oepen and Vögtle in 1979 recorded the formation of a number of ‘neutral molecule complexes’ between urea (ur) and/or thiourea (tu) and a number of N,N′-aromatic chelate bases derivative of 2,2′-bipyridine (bpy), motifs now widely utilized in essays in studies of molecular/crystal architecture. The structures are recorded of a number of their adducts, namely (a) bpy/ur (1 : 1), (b) phen/ur (1 : 1), (c) phen/tu (1 : 1), (d) dmp/ur (1 : 1), together with (e) bpy/tu (1 : 1) and (f) a dmp/tu adduct of 1 : 2 stoichiometry (phen = 1,10-phenanthroline; dmp = 2,9-dimethyl-1,10-phenanthroline). Association takes places in all cases by way of hydrogen-bonding interactions between alternating (thio-)urea NH2 groups which form an infinite band with the nitrogen atoms of the aromatic base at the periphery, the base planes quasi-normal to that of the band, as in the archetypical 2,6-lutidine/urea (1 : 1) array, described long ago.

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