Synthesis of 4-oxothiazolidine-2,5-diylidenes containing thioamide group based on dithiomalonamides

4-Methoxybenzyl cations bearing α-(N,N-dimethylcarbamoyl) and α-(N,N-dimethylthiocarbamoyl) substituents have been generated photochemically upon irradiation of precursors with pentafluorobenzoate or 4-methoxybenzoate leaving groups. The ions have been observed with flash photolysis in 40:60 acetonitrile:water and in 50:50 methanol:water, and rate constants were measured for their decay in solvent alone and for their capture by azide ion. The cations so studied and their lifetimes in 40% acetonitrile are 6, ArC+H-CONMe2, 0.6 μs; 2, ArC+H-CSNMe2, 7 ms; and 4, ArC+(CH3)-CSMe2, 6 ms, where Ar = 4-MeOC6H4. The cation 4 reacts with solvent by elimination of a proton from the α-methyl group, and the rate constant for solvent addition must be less than 1 s-1. The CSNMe2 substituted cations are 105-107-fold longer lived than analogs where the thioamide group has been replaced with an α-methyl. The UV-visible absorption spectra of these two cations also show significant differences from those of typical 4-methoxybenzyl cations. Thus, both the lifetimes and spectra point to a strong interaction of the benzylic centre with the thioamide group. Key words: flash photolysis, thiocarbamoyl stabilized carbocation, photosolvolysis.

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Toxicity assessment of 255 chemicals to pure cultured nitrifying bacteria using biosensor

Water Science & Technology ◽

10.2166/wst.2002.0758 ◽

2002 ◽

Vol 46 (11-12) ◽

pp. 331-335 ◽

Cited By ~ 7

Author(s):

Y. Tanaka ◽

K. Taguchi ◽

H. Utsumi

Keyword(s):

Functional Group ◽

Synergistic Effects ◽

Toxicity Assessment ◽

Inhibition Test ◽

Nitrifying Bacteria ◽

Inhibition Rate ◽

Thioamide Group ◽

Chemical Contaminant ◽

Mixed Samples

The bioassay has been attracting attention as a method of toxicity assessments of micropollutants in the environment. In this study, we report the characteristics (selectivity and sensitivity) of the nitrifying bacteria biosensor for 255 kinds of chemicals as a model of chemical contaminant in the environment and the results of evaluation of mixed samples of several substances. In the nitrifying bacteria respiration inhibition test using the biosensor, 56 chemicals were detected. It was found that this biosensor is especially sensitive to seven chemicals that have a thiocarbonyl functional group (>C=S), such as a thioamide group of thiocarbamate group. These chemicals are considered to specifically inhibit AMO by chelation of copper. The samples consisted of a mixture of seven types of anilines that inhibit respiration in the bacteria, a mixture of five types of chlorophenols, and a mixture of eight types of substances that contain thiocarbonyl groups were examined. All of the mixed samples inhibited the respiration of the nitrifying bacteria more than 10% by the inhibition rate, and observed a synergistic effects of the substances in the samples.

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Synthesis and characteristics of chelating fibers containing imidazoline group or thioamide group

Journal of Applied Polymer Science ◽

10.1002/app.10156 ◽

2001 ◽

Vol 83 (7) ◽

pp. 1608-1616 ◽

Cited By ~ 39

Author(s):

Ruixia Liu ◽

Yi Li ◽

Hongxiao Tang

Keyword(s):

Thioamide Group

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Synthesis of New Imidazolidine and Tetrahydropyrimidine Derivatives

Advances in Chemistry ◽

10.1155/2014/834641 ◽

2014 ◽

Vol 2014 ◽

pp. 1-4 ◽

Cited By ~ 1

Author(s):

Hamid Beyzaei ◽

Reza Aryan ◽

Zahra Keshtegar

Keyword(s):

Ring Opening ◽

Reaction Times ◽

Reaction Conditions ◽

Ir Spectrometry ◽

H Nmr ◽

Chemical Structures ◽

Thioamide Group ◽

Solvent Free Conditions ◽

Ft Ir ◽

C Nmr

Synthesis of new imidazolidine and tetrahydropyrimidine derivatives 3a, b and 4a–c as cyclic 1,3-diamines under two reaction conditions (A and B) is described. Under reaction conditions-A, a suspension of (E)-2-cyano-2-(oxazolidin-2-ylidene)ethanethioamide 1 (1 eq.) and diaminoalkanes 2a–e (2 eq.) in absolute ethanol is heated under reflux for 16–22 h to afford 3a, b and 4a–c. Alternatively, under reaction conditions-B, a solution of thioamide 1 (1 eq.) in diaminoalkanes 2a–e (3 eq.) is stirred under solvent-free conditions at room temperature for 3 days to give desired products. Reaction conditions-A for having higher yields, shorter reaction times, and required less diamines is more effective than reaction conditions-B. Oxazolidine ring opening is observed by reacting compound 1 with all of the diamines 2a–e, but the thioamide group only reacts with nonbulky diamines 2a, b. The chemical structures of novel compounds were confirmed by 1H NMR, 13C NMR, elemental analysis, and FT-IR spectrometry.

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1-(4-Chlorobutanoyl)-3-(2-nitrophenyl)thiourea

Acta Crystallographica Section E Structure Reports Online ◽

10.1107/s160053681202168x ◽

2012 ◽

Vol 68 (6) ◽

pp. o1801-o1801 ◽

Cited By ~ 2

Author(s):

Nurziana Ngah ◽

Maisara Kadir ◽

Bohari M. Yamin ◽

M. Sukeri M. Yusof

Keyword(s):

Hydrogen Bonding ◽

Benzene Ring ◽

Title Compound ◽

Dihedral Angles ◽

Intermolecular Hydrogen Bonding ◽

Asymmetric Unit ◽

Compound C ◽

Thioamide Group ◽

Independent Molecules

The asymmetric unit of the title compound, C11H12ClN3O3S, contains two independent molecules with different conformations in which the benzene ring and the thiourea fragment form dihedral angles of 87.28 (12) and 66.44 (10)°. The O atom of the thioamide group is involved in bifurcated N—H...O intra- and intermolecular hydrogen bonding; the latter interaction links the independent molecules into a dimer. In the crystal, N—H...S interactions link the molecules into chains propagating along the c axis.

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Determination of the substituent constant σp- for the thioamide group -CSNH2 from the ionization of anilines and phenols

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19912964 ◽

1991 ◽

Vol 56 (12) ◽

pp. 2964-2968 ◽

Cited By ~ 8

Author(s):

Miroslav Polášek ◽

Karel Waisser ◽

Tomáš Bouček

Keyword(s):

Ultra Violet ◽

Ionization Constants ◽

Amino Group ◽

Substituted Phenols ◽

Substituent Constant ◽

Substituted Anilines ◽

Phenolic Hydroxy Group ◽

Thioamide Group ◽

Phenolic Hydroxy

Thermodynamic ionization constants pKa 2.62 ± 0.01 for the primary aromatic amino group of 4-aminothiobenzamide and pKa 8.28 ± 0.01 for the phenolic hydroxy group of 4-hydroxythiobenzamide have been determined by ultra-violet spectrophotometry at 25°C. By using these pKa values and the Hammett equations (log Ka vs σ) for the ionization of fourteen 3- or 4-substituted phenols and thirteen 3- or 4-substituted anilines the substituent constant σp- = 0.68 (from the ionization of anilines) or σp- = 0.73 (from the ionization of phenols) of the thioamide group -CSNH2 was calculated.

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Efficient adsorption of gold ions from aqueous systems with thioamide-group chelating nanofiber membranes

Chemical Engineering Journal ◽

10.1016/j.cej.2013.06.022 ◽

2013 ◽

Vol 229 ◽

pp. 420-428 ◽

Cited By ~ 77

Author(s):

Xiang Li ◽

Chengcheng Zhang ◽

Rui Zhao ◽

Xiaofeng Lu ◽

Xiuru Xu ◽

...

Keyword(s):

Aqueous Systems ◽

Thioamide Group ◽

Nanofiber Membranes

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Antimycobacterial thiobenzanilides

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19900307 ◽

1990 ◽

Vol 55 (1) ◽

pp. 307-316 ◽

Cited By ~ 10

Author(s):

Karel Waisser ◽

Nestor Houngbedji ◽

Miloš Macháček ◽

Miroslav Sekera ◽

Josef Urban ◽

...

Keyword(s):

Silica Gel ◽

Nmr Spectra ◽

Chemical Shifts ◽

Antimycobacterial Activity ◽

Uv Spectra ◽

Mycobacterium Kansasii ◽

Aromatic Rings ◽

H Nmr ◽

Hammett Constants ◽

Thioamide Group

A group of 30 thiobenzanilides active against Mycobacterium kansasii have been synthesized and their 1H NMR and UV spectra and RM values (TLC on silica gel impregnated with methylsilicone oil) have been measured. From the correlation between the chemical shifts of the thioamide proton in the 1H NMR spectra and the Hammett constants it can be concluded that the substituents in both aromatic rings uniformly affect the electron density of the thioamide group. The antimycobacterial activity is probably connected with local molecular parameters and can be considered to be approximately additive with respect to both parts of the molecule.

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