The Crystal and Molecular Structure of 3-Isopropyl-5-phenylrhodanine.

Rang, Knut; Sandström, Jan; Thell, Lars; Yang, Qibin; Datema, Roelf; Chattopadhyaya, J.

doi:10.3891/acta.chem.scand.39b-0123

Cited by 8 publications

(6 citation statements)

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“…The same kind of bisected conformation was found in the crystal structure of 3-isopropyl-5-phenylrhodanine. 21 By analogy with 3-isopropyl-⌬ 4 -1,3thiazoline-2-thiones, 22 the free energy barrier for A → B exchange in 3-isopropyl-5-phenylrhodanine can be estimated to be at least 10 kcal mol −1 . Still, the 1 H NMR resonances of this compound in dichloromethane-d 2 solution did not show any perceptible broadenings down to −90°C.…”

Section: Crystal Structures and Conformationsmentioning

confidence: 99%

Diastereomers of 3-(S)-(1-phenylethyl)-5-methyl- and -5-phenylrhodanine: Crystal structures, conformations, and circular dichroism spectra

et al. 1997

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3‐(S)‐(1‐phenylethyl)‐5‐methyl‐ and 5‐phenyl‐rhodanine have been studied by single crystal X‐ray crystallography. The crystals of the 5‐methyl compound were shown to contain equal amounts of the 5‐(R) and 5‐(S) diastereomers, while the crystals of the 5‐phenyl compound only contain the 5‐(S) diastereomer. The UV and CD spectra of the 5‐H2 compound have been analyzed on the basis of CNDO/S calculations, and the CD spectrum has been reproduced by semiempirical calculations. The 5‐methyl diastereomers can be partly separated by chromatography on triacetylcellulose, and the CD spectra of the individual forms can be evaluated. The 5‐phenyl compound undergoes rapid epimerization in solution, and also for this compound the CD spectra of both forms can be evaluated. The contribution of the 5‐substituent follows Ripperger's sector rule for dithiocarbamates. Chirality 9:568–577, 1997. © 1997 Wiley‐Liss, Inc.

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Section: Crystal Structures and Conformationsmentioning

confidence: 99%

Diastereomers of 3-(S)-(1-phenylethyl)-5-methyl- and -5-phenylrhodanine: Crystal structures, conformations, and circular dichroism spectra

et al. 1997

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“…The electronic structure and tautomerism of rhodanines have been studied experimentally and theoretically by two groups [1,2]. In addition, modeling has been performed on rhodanines using various approximate methods (see, e.g., [3][4][5]). Among the quantum mechanical methods used have been PPP-SCF-CI, CNDO/2, MINDO/3, ~Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana.…”

Section: Introductionmentioning

confidence: 99%

“…MNDO, AM1, PM3, and ab initio with basis sets as large as 4-31G(d/S) [1][2][3][4]. In addition, the molecular mechanics method in CHEMLAB-II has been tried on an ylidene rhodanine [5].…”

Section: Introductionmentioning

confidence: 99%

Molecular orbital study of the structure and interactions of ylidene rhodanines

1996

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Semiempirical (with the AM1 Hamiltonian) and ab initio (mainly with the 6-31G* and LANL2DZ + + (d,p) basis sets) molecular oribital calculations show the predominant tautomer of gas phase methylidene rhodanine is 2-thioxo--4-thiazolidinone in agreement with earlier work on other types of rhodanines. Inclusion of solvation effects in the AM 1 calculations corroborates with this tautomer is also preferred in aqueous solution. Energy-optimized bond lengths and angles show good agreement with those for a crystalline benzylidene rhodanine. The geometry of a hydrogen bonded dimer matches closely the crystalline state arrangement. The two N--H 9 9 9 O hydrogen bonds that form in the dimer provide a stabilization energy of about -10 kcal/mol. The interactions of methylidene rhodanine with a calcium ion are modeled with basis sets as large as LANL2DZ+ + (d,p). The preferred binding site is near the carbonyl oxygen for the neutral rhodanine and near the nitrogen and thione sulfur in a bidentate arrangement for the rhodanine anion. Implications for the interaction of benzylidene rhodanines with various possible protein and metalloprotein receptors are discussed.

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“…A series of sodium dithiocarbamate salts, Na[ 1 a–e ], was prepared in almost quantitative yield from the exothermic reaction of carbon disulfide with primary amines in diethyl ether in the presence of sodium hydroxide, Equation 1 [28] . The use of an excess of isopropylamine led to the ammonium dithiocarbamate [NH 3 i Pr][ 1 b ], Equation [29] …”

Section: Resultsmentioning

confidence: 99%

“…Synthesis and characterization of isopropylammonium N‐isopropyldithiocarbamate, [NH 3 i Pr][S 2 CNH i Pr] ([NH 3 i Pr][1 b]) [29] …”

Section: Methodsmentioning

confidence: 99%

4‐Aryl‐2‐Imino‐1,3‐Dithiolanes from the Room Temperature Coupling of Sodium Dithiocarbamates with Sulfonium Salts

et al. 2021

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The Crystal and Molecular Structure of 3-Isopropyl-5-phenylrhodanine.

Cited by 8 publications

References 0 publications

Diastereomers of 3-(S)-(1-phenylethyl)-5-methyl- and -5-phenylrhodanine: Crystal structures, conformations, and circular dichroism spectra

Diastereomers of 3-(S)-(1-phenylethyl)-5-methyl- and -5-phenylrhodanine: Crystal structures, conformations, and circular dichroism spectra

Molecular orbital study of the structure and interactions of ylidene rhodanines

4‐Aryl‐2‐Imino‐1,3‐Dithiolanes from the Room Temperature Coupling of Sodium Dithiocarbamates with Sulfonium Salts

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