<i>N</i>-(<i>p</i>-Tolyl)thioacetamide

Śmiszek-Lindert, Wioleta; Nowak, Maria; Kusz, Joachim

doi:10.1107/s1600536807041633

Cited by 3 publications

(4 citation statements)

References 9 publications

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“…We next determined the crystal structures of the E isomers of secondary N–H thioamides 3a and the corresponding N–H amides 3c (Figure a, b and see Figures S4–S10). The E isomer of 3a is the major isomer in polar solvents, and in the case of amide 3c , the E isomer of 3c is the major isomer in all the solvents studied here.…”

Section: Resultsmentioning

confidence: 99%

Contribution of Solvents to Geometrical Preference in the Z/E Equilibrium of N-Phenylthioacetamide

et al. 2021

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We studied the Z/E preference of N-phenylthioacetamide (thioacetanilide) derivatives in various solvents by means of 1 H NMR spectroscopy, as well as molecular dynamics (MD) and other computational analyses. Our experimental results indicate that the Z/E isomer preference of secondary (NH)thioamides of N-phenylthioacetamides shows substantial solvent dependency, whereas the corresponding amides do not show solvent dependency of the Z/E isomer ratios. Detailed study of the solvent effects based on molecular dynamics simulations revealed that there are two main modes of hydrogen (H)-bond formation between solvent and (NH)thioacetamide, which influence the Z/E isomer preference of (NH)thioamides. DFT calculations of NH-thioamide in the presence of one or two explicit solvent molecules in the continuum solvent model can effectively mimic the solvation by multiple solvent molecules surrounding the thioamide in MD simulations and shed light on the precise nature of the interactions between thioamide and solvent. Orbital interaction analysis showed that, counterintuitively, the Z/E preference of NH-thioacetamides is mainly determined by steric repulsion, while that of sterically congested N-methylthioacetamides is mainly determined by thioamide conjugation.

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Section: Resultsmentioning

confidence: 99%

Contribution of Solvents to Geometrical Preference in the Z/E Equilibrium of N-Phenylthioacetamide

et al. 2021

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“…The title compounds were synthesized by utilizing the method described by Śmiszek-Lindert et al , Crystals of 3MTA and 4MTA, which proved to be suitable for our spectral studies, were obtained by crystallization from melted samples occurring between two closely spaced CaF 2 windows. In this way, thin enough crystals could be obtained, characterized by a maximum absorbance at the ν N–H band frequency range close to 0.5.…”

Section: Methodsmentioning

confidence: 99%

“…Crystals of 4-methylthioacetanilide (4MTA) belong to the orthorhombic system. 32 The space-symmetry group is Pbca D 2h 15 . The lattice constants at 298 K: a = 13.6695(9) Å, b = 8.7917(5) Å, c = 14.9870(8) Å, R = β = γ = 90°, and Z = 8.…”

Section: Introductionmentioning

confidence: 99%

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H/D Isotopic Recognition in Hydrogen-Bonded Systems: Strong Dynamical Coupling Effects in the Polarized IR Spectra of 3-Methylthioacetanilide and 4-Methylthioacetanilide Crystals

2011

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This paper presents the investigation results of the polarized IR spectra of the hydrogen bond in crystals of 3- and 4-methylthioacetanilide. The spectra were measured at 293 and 77 K by a transmission method, with the use of polarized light. The main spectral properties of the crystals can be interpreted satisfactorily in terms of the "strong-coupling" theory, on the basis of the hydrogen bond centrosymmetric dimer model. The spectra revealed that the strongest vibrational exciton coupling involved the closely spaced hydrogen bonds, each belonging to a different chain of associated 3- and 4-methylthioacetanilide molecules. A weaker exciton coupling involved the adjacent hydrogen bonds in each individual chain. It was proven that a nonrandom distribution of the protons and deuterons took place in the lattices of isotopically diluted crystalline samples of 3- and 4-methylthioacetanilide. In each case, the H/D isotopic "self-organization" mechanism involved all four hydrogen bonds from each unit cell.

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Hirshfeld surface analysis and spectroscopic and DFT studies of p-acetotoluidide and p-thioacetotoluidide

2016

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N-(p-Tolyl)thioacetamide

Abstract: Key indicators: single-crystal X-ray study; T = 298 K; mean (C-C) = 0.002 Å; R factor = 0.036; wR factor = 0.113; data-to-parameter ratio = 28.9.

Cited by 3 publications

References 9 publications

Contribution of Solvents to Geometrical Preference in the Z/E Equilibrium of N-Phenylthioacetamide

Contribution of Solvents to Geometrical Preference in the Z/E Equilibrium of N-Phenylthioacetamide

H/D Isotopic Recognition in Hydrogen-Bonded Systems: Strong Dynamical Coupling Effects in the Polarized IR Spectra of 3-Methylthioacetanilide and 4-Methylthioacetanilide Crystals

Hirshfeld surface analysis and spectroscopic and DFT studies of p-acetotoluidide and p-thioacetotoluidide

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