The Role of Organic Fluorine in the Supramolecular Assembly of Halogenated β-Hydroxysulphoxides Diastereomers

2006 ◽  
Vol 6 (12) ◽  
pp. 2769-2778 ◽  
Author(s):  
Gregorio Asensio ◽  
Mercedes Medio-Simon ◽  
Pedro Alemán ◽  
Carmen Ramírez de Arellano
2014 ◽  
Vol 70 (a1) ◽  
pp. C669-C669
Author(s):  
Angshuman Roy Choudhury ◽  
Gurpreet Kaur ◽  
Maheswararao Karanam ◽  
Sandhya Patel

The phrase "Organic fluorine" [1] was introduced by Dunitz and Taylor in 1997 to identify the C–F bonds in organic systems. Different research groups have used the phrase to glorify or deny the influence of C–F bond in crystal lattices. Once Dunitz stated that "Organic Fluorine: Odd Man Out" and Howard et al. questioned the role of "Organic fluorine" in crystal engineering. While some researchers have refuted the role of "organic fluorine" in crystal packing; the others indicated the importance of the interactions involving the same group. A number of publications have shown the importance of "Organic fluorine" in influencing crystal packing. We have been interested in the area of weak interactions in organic solid state chemistry since 1999 [2]; especially interactions involving "Organic fluorine". The study is being conducted following a systematic approach and is still in progress. We have looked at the structures of a number if tetrahydroisoquinoline derivatives, a number of differently substituted imines, phenyleacetanilydes, benzanilides and azobenzenes [3] etc. in order to elucidate the influence of "Organic fluorine" in crystal engineering both in the presence and in the absence of strong hydrogen bonding functional groups present within the molecule. A short summary of our observations will be highlighted in the presentation.


2000 ◽  
Vol 78 (6) ◽  
pp. 723-731 ◽  
Author(s):  
Stefano Roelens ◽  
Paolo Dapporto ◽  
Paola Paoli

A new H-bonded supramolecular assembly of the diamine-diol family has been obtained from (1R,2R)-1,2-diaminocyclohexane (DAC) and (S)-1-phenyl-1,2-ethanediol (PED). The structure was characterized by single-crystal X-ray analysis and showed the typical architecture of DAC based assemblies, consisting of a three-stranded helicate coiling around a H-bonded core, with a predictable helicity sense determined by the configuration of DAC. The new assembly, while reconfirming the unique role of DAC as a powerful assembler of supramolecular structures, demonstrated that the C2 symmetry of diol partners employed so far is not essential for assembling helicates, although chirality is. In the case of the adduct between (1R,2R)-1,2-diaminocyclohexane and (2R,3R)-2,3-butanediol, molecular recognition and self-assembly have been shown to take place even in the absence of solvent, in the gas phase, where long crystals were formed by spontaneous organized aggregation of diamine-diol units. A thorough analysis of the results from the present and previous investigations has lead to a deeper understanding of the key features of the diamine-diol molecular code and of the requirements for recognition and assembly.Key words: supramolecular, hydrogen bonding, molecular recognition, self-assembly, diamines, diols.


2011 ◽  
Vol 47 (27) ◽  
pp. 7677 ◽  
Author(s):  
Marta Castelaín ◽  
Horacio J. Salavagione ◽  
Rafael Gómez ◽  
José Luis Segura

2015 ◽  
Vol 429 ◽  
pp. 1-14 ◽  
Author(s):  
Ghodrat Mahmoudi ◽  
Ali Akbar Khandar ◽  
Jan K. Zaręba ◽  
Michał J. Białek ◽  
Masoumeh Servati Gargari ◽  
...  

1985 ◽  
Vol 227 (1) ◽  
pp. 57-65 ◽  
Author(s):  
S Vannucchi ◽  
M Ruggiero ◽  
V Chiarugi

In a series of attempts to reveal plasma heparin, we found that high ionic strength and modification of protein amino groups were not effective in extracting endogenous heparin (or, indeed, a large percentage of exogenous labelled heparin), whereas delipidation in the presence of 4M-guanidinium chloride gave high yields, indicating that plasma heparin may be assembled with compounds other than proteins, in a form making it inaccessible to water and ions. During the extraction of lipids, a paradoxical entry of heparin into the organic phase was observed. Detergents, including sodium dodecyl sulphate, did not shift heparin into the aqueous phase, whereas repeated chloroform/methanol extraction did so. Using purified compounds we were able to reproduce in vitro both the scavenging of heparin from water as well as the formation of heparin-phosphatidylcholine complexes soluble in organic solvents. Evidence for complexing of heparin with phosphatidylcholine was also obtained by electrophoretic and ultracentrifugation assays. The quaternary-ammonium-containing phosphatidylcholine was the more effective phospholipid in binding heparin; anionic phospholipids did not bind. Only heparin-like glycosaminoglycans bound phosphatidylcholine, but less-sulphated compounds (heparan sulphate and dermatan sulphate) were weaker ligands. Gel-filtration experiments showed that heparin was not bound to liposome vesicles, but that a measurable percentage of the phospholipids was stripped off from vesicles and was found in the form of a complex separable from liposomes by gel filtration. The molecular basis as well as the biological role of the interaction of heparin with major membrane phospholipids are discussed.


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