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1

Preparation and Structure of Optically Active Imidazolium Tetrafluoroborates; in Search of New Chiral Ionic Liquids

Mlostoń G., Mucha P., Tarka R., Urbaniak K., Linden A., Heimgartner H.

Polish Journal of Chemistry

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2009

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Vol. 83, nr 6

1105-1114

EN

Enantiomerically pure (R)-1-(1-phenylethyl)imidazoles 4a,b can be prepared conveniently from alfa-(hydroxyimino)ketones 1, (R)-1-phenylethylamine and form aldehyde, fol lowed by deoxygenation with Raney-Ni. Similarly, the reaction with (R,R)-trans-cyclohexane-1,2-diamine yields enantiomerically pure (R,R)-trans-1,1'-cyclohexane-1,2-diyl)imidazoles 4c,d. Alkylation of these imidazole derivatives with alkylbromides leads to the corresponding 3-alkylimidazolium bromides 6 and 8, respectively, which on treatment with sodium tetrafluoroborate are transformed into the correspond ing tetrafluoroborates 7 and 9. Whereas some of the imidazolium salts 7 show properties of chiral ionic liquids, the bis-imidazolium tetrafluoroborates 9 are high-melting crystalline materials.

2

Ambivalent Nucleophilicity of 1,4,5-Trisubstituted Imidazole-2-thiones in Reactions with Dimethyl Acetylenedicarboxylate and Phenylisocyanate

Mlostoń G., Gendek T., Linden A., Heimgartner H.

Polish Journal of Chemistry

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2008

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Vol. 82, nr 8

1561-1561

EN

The 1,4,5-trisubstitued 2,3-dihydro-1H-imidazole-2-thiones 1 react with electrophilic re agents via the S- or the N(3)-atom. The reaction with dimethyl acetylenedicarboxylate in methanol at room temperature occurs by the nucleophilic addition of the S-atom to give the corresponding 2-[(1H-imidazol-2-yl)sulfanyl]fumarates 4 in high yield. On the other hand, imidazole-2-thiones 1 react with phenylisocyanate in dichloromethane at room temperature to yield 2,3-dihydro-2-thioxo-1H-imidazole-1-carboxamides 5. The structures of both types of adducts were established by X-ray crystallography.

3

Synthesis and Characterization of Novel Phosphorictriamide Derivatives with Morpholine Substituents: Crystal Structures of Substituents: Crystal Structures of (CF3)C(O)NHP(O)(NC4H8O)2 and (p-Br-C6H4)C(O)NHP(O)(NC4H8O)2

Gholivand K., Mojahed F., Alizadehgan A.

Polish Journal of Chemistry

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2007

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Vol. 81, nr 3

393-402

EN

Using phosphorus pentachloride as a substrate, carbacylamidophosphates of the general formula (R)C(O)NHP(O)(NC4H8O)2, where R = CH2Cl I; CHCl2 II; CCl3 III; CF3 IV; p-Me-C6H4V; p-Br-C6H4 VI; p-Cl-C6H4 VII, were prepared and characterized by 1H, 31P and 13C NMR, IR spectroscopy and elemental analysis. Different carboxylic amides attached to phosphorus nuclei affect on IR and NMR spectra. Three-bond coupling constants between phosphorus and carbon nucleus, 3J(P,Caliphatic) in the synthesized compounds, were greater than two-bond coupling constants, 2J(P,Caliphatic). The structures of IV and VI were determined by single-crystal X-ray diffraction techniques. The compounds IV and VI formed centrosymmetric dimers via intermolecular N-HźźźO=P hydrogen bonds.

4

Synthesis and Characterization of Novel Carbacylamidophosphate Derivatives: Crystal Structures of (CF3)C(O)NHP(O)(NC6H12)2, (p-Br-C6H4)C(O)NHP(O)(NC6H12)2 and (p-Cl-C6H4)C(O)NHP(O)(NC6H12)2

Gholivand K., Mojahed F., Alizadehgan A. M.

Polish Journal of Chemistry

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2007

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Vol. 81, nr 10

1829-1829

EN

Several new arbacylamidophosphates with formula (X)C(O)NHP(O)(NC6H12)2, X =CH2Cl, 1b; CHCl2, 2b; CCl3, 3b; CF3, 4b; MeC6H4, 5b; BrC6H4, 7b; ClC6H4, 8b were synthesized and characterized by 1H, 31P and13C NMR and IR spectroscopy and elemental analysis. The effect of PNCC dihedral angles on the 3J(P,C aliphatic) was studied. The structures of the 4b, 7b and 8b were determined by single-crystal X-ray diffraction techniques. The structural data of these compounds are compared with similar carbacylamidophosphates.

5

Transformation of O-Amidinylhydroxylamine into Benzothiazoles via Iminocarbonyl Sulfenamides

Sączewski F.., Kornicka A., Gdaniec M.

Polish Journal of Chemistry

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2005

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Vol. 79 / nr 1

115-120

EN

The reaction of O-amidinylhydroxylamine 3 with aryl isothiocyanates leads to the formation of benzothiazole derivatives 5a-c. The proposed mechanism of the reaction involves initial formation of iminocarbonyl sulfenamides A which, in turn, undergo spontaneous sulfurization of aromatic ring with loss of amine 7. The later compound reacts with excess aryl isothiocyanate to give ,3-diazaspiro[4,5]decane-2-thione 6.

6

Badania nad otrzymaniem krystalicznych form niektórych flawonoidów, ich sulfonowych pochodnych oraz kompleksów z jonami metali

Pusz J., Nitka B., Kopacz S.

Zeszyty Naukowe Politechniki Rzeszowskiej. Chemia

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2004

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z. 19 [216]

147--161

PL

Zbadano 276 układów do krystalizacji moryny, chryzyny, kwercetyny, ich sulfonowych pochodnych oraz kompleksów z jonami metali. Uzyskano formy krystaliczne dla moryny i soli sodowej kwasu moryno-5'-sulfonowego (NaMSA), sulfonowych pochodnych kwercetyny - kwasu kwercetyno-5'-sulfonowego (QSA-5') i soli sodowej kwasu kwercetyno-8,5'-disulfonowego (Na2QDSA) oraz kompleksów In(III) i Fe(IlI) z chryzyną, które zbadano metodą rentgenografii strukturalnej. Uzyskane wyniki wskazują, że QSA-5' może mieć układ regularny, tetragonalny lub heksagonalny, natomiast pozostałe związki - układ jednoskośny lub trójskośny. Wykonano zdjęcia uzyskanych form krystalicznych metodą elektronowej mikroskopii skaningowej.

EN

The 276 systems to receipt crystalline forms of morin, chrysin, quercetin, their sulphonic derivatives and complexes of metal ions were examined. The crystalline forms of morin, sodium salt of morin-5'-sulphonic acid (NaMSA), quercetin-5'-sulphonic acid (QSA-5'), sodium salt of quercetin-8,5'-disulphonic acid (Na2QDSA) and complexes of In(III) and Fe(III) ions with chrysin were obtained. The method of structural X-rays radiography and electron scanning microscopy were used.

7

Structural and vibrational studies of the molecular crystal formed by benzenamine with trifluoroacetic acid

Baran J., Barnes A. J., Barycki J., Pietraszko A., Ratajczak H.

Bulletin of the Polish Academy of Sciences. Chemistry

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2001

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Vol. 49, No. 2

115-124

EN

The crystal structure of benzenamine-trifluoroacetic acid has been found to belong to the P2i space group of the monoclinic system, with Z = 8, o = 10.294(2) A, b = 9.126(2) A, c = 20.603(4) A, and Beta = 98.77(3)°. In the crystal the amine is protonated and the resulting benzenammonium and trifluoroacetate ions are interlinked by a network of N—H- • -O hydrogen bonds. The observed infrared spectrum is in accordance with such a structure.