Bis[(<i>S</i>)-(−)-α-methylbenzyl]thiourea

Bailey, Philip J.; Grant, Keith J.; Parsons, Simon

doi:10.1107/s010827019601298x

Cited by 8 publications

(9 citation statements)

References 1 publication

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“…The whole molecule thus approximates a local C 2 point symmetry. The observed conformation is identical to that found in other related homosubstituted thioureas (Lai & Tiekink, 2002;Bailey et al, 1997).…”

Section: Sup-1supporting

confidence: 85%

“…For general background about solvent-free synthesis, see: Tanaka & Toda (2000); Jeon et al (2005). For C 2 homosubstituted thioureas, see: Bailey et al (1997); Lai & Tiekink (2002). For common hydrogen-bonding schemes in thioureas, see: Vá zquez et al (2004); Custelcean et al (2005); Shashidhar et al (2006);Sadiq-ur-Rehman et al (2007); Saxena & Pike (2007).…”

Section: Related Literaturementioning

confidence: 99%

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(+)-(S,S)-1,3-Bis[(tetrahydrofuran-2-yl)methyl]thiourea

2008

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The title compound, C11H20N2O2S, is an enantiomerically pure heterocycle-substituted thiourea synthesized under solvent-free conditions. The thiourea unit adopts a ZZ conformation, with the HN—(C=S)—NH core almost planar and the tetrahydrofurfuryl groups placed below and above this plane. The whole molecule thus approximates to noncrystallographic C 2 symmetry. Unexpectedly, the C=S group is not involved in intermolecular hydrogen bonding, as generally observed in homodisubstituted thioureas. Instead, molecules form a one-dimensional network based on weak N—H⋯O(heterocycle) hydrogen bonding, resulting in a zigzag ribbon-like structure around the crystallographic 21 screw axis along [100].

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Section: Sup-1supporting

confidence: 85%

Section: Related Literaturementioning

confidence: 99%

(+)-(S,S)-1,3-Bis[(tetrahydrofuran-2-yl)methyl]thiourea

2008

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“…1, differ significantly from one another but are short in comparison with the typical value for an N-C single bond (1.479 Å). Owing to the introduction of the C=O electron-acceptor group the adjacent C-S bond length [1.652 (2)Å ] is shorter than previously reported C=S distances (1.710 (7)Å) (Bailey, et al, 1997). These distances are similar to those usually found in other substituted thioureas (Khawar Rauf et al, 2006a, 2006b, 2006c, 2007, 2009.…”

Section: Data Collectionsupporting

confidence: 70%

“…For bond lengths in other other substituted thioureas, see: Khawar Rauf et al (2006aRauf et al ( ,b,c, 2007Rauf et al ( , 2009. For previously reported C S distances, see: Bailey et al (1997). Mo K radiation = 0.46 mm À1 T = 293 K 0.30 Â 0.20 Â 0.20 mm…”

Section: Related Literaturementioning

confidence: 99%

1-(2,6-Dichlorobenzoyl)-3-(3-nitrophenyl)thiourea dimethylformamide solvate

Hou

2010

Acta Cryst E

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In the title compound, C14H9Cl2N3O3S·C3H7NO, the two aromatic rings enclose a dihedral angle of 32.93 (12)°. The thiourea molecule exists in its thione form in the solid state with typical C=S and C—N bond lengths. In the crystal, N—H...O hydrogen bonds exist between the thiourea and carbonyl groups on the same and neighboring molecules. In addition, each dimethylformamide solvate molecule forms a hydrogen bond to one N atom of the thiourea group

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“…Inappropriate reproduction of band intensities might also partially contribute to the differences between experimental and theoretical spectra. In any case, it is worth noting that a fairly perturbed conformation ( α 1 =+26.68°, α 2 =+9.95°) was also found in the solid‐state structure of PETU …”

Section: Resultsmentioning

confidence: 77%

Towards an Observation of Active Conformations in Asymmetric Catalysis: Interaction‐Induced Conformational Preferences of a Chiral Thiourea Model Compound

Kreienborg

Pollok

Merten

2016

Chemistry A European J

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The observation of the active species is the goal of most spectroscopic investigations on enantioselective organocatalysts in solution. Although NMR spectroscopy is widely applied, it has low sensitivity for conformational changes or the chiral nature of the interactions. In the present work, we exemplify the use of vibrational circular dichroism (VCD) spectroscopy for the characterization of a chiral thiourea model compound in nonpolar and polar solvents, as well as for a detailed analysis of its interaction with a model reactant. We discuss solvent-induced conformational changes of the thiourea, and provide evidence for an unexpected binding topology between the thiourea and an acetate anion. The results clearly showcase the possibilities offered by using VCD spectroscopy in the characterization of chiral organocatalysts.

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Bis[(S)-(−)-α-methylbenzyl]thiourea

Cited by 8 publications

References 1 publication

(+)-(S,S)-1,3-Bis[(tetrahydrofuran-2-yl)methyl]thiourea

(+)-(S,S)-1,3-Bis[(tetrahydrofuran-2-yl)methyl]thiourea

1-(2,6-Dichlorobenzoyl)-3-(3-nitrophenyl)thiourea dimethylformamide solvate

Towards an Observation of Active Conformations in Asymmetric Catalysis: Interaction‐Induced Conformational Preferences of a Chiral Thiourea Model Compound

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