Structure of N-(2-hydroxyethyl)-2-thiofuramide

Galešić, N.; Vlahov, Alexander; Galešić, Mirna

doi:10.1107/s0108270187095313

Cited by 2 publications

(2 citation statements)

References 8 publications

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“…Such supramolecular synthons form infinite chains C(4), like in structures 1-3 (N-H· · ·O=C) and 5 (N-H· · ·S=C). Such Table 6 13 C NMR chemical shifts (δ/ppm) a and C-H coupling constants (J/Hz) b of compounds 1-5 chains are also formed in N-(2-chloroethyl)-2-furamide [29], while in N-(2-hydroxyethyl)-2-thiofuramide [33] hydrogenbonded dimers are formed through N-H· · ·OH intermolecular HB with hydroxyl group. The dimers are further connected in layers by the O-H· · ·S( = C) hydrogen bond of 3.255(3) Å.…”

Section: Crystal Structures Descriptionmentioning

confidence: 97%

Supramolecular amide and thioamide synthons in hydrogen bonding patterns of N-aryl-furamides and N-aryl-thiofuramides

et al. 2006

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The supramolecular synthon of amide group in the primary and secondary amides is well recognized to be infinite chains of the C(4) type formed by the intermolecular hydrogen bond of the type N-H· · ·O=C. On the other hand, there is a lack of structural data for the thioamides. Three compounds belonging to the class of N-aryl-furamides (N-(4-bromophenyl)-5-bromo-2-furancarboxamide, N-(4-chlorophenyl)-5-bromo-2-furancarboxamide) and to the class of N-aryl-thiofuramide (N-(4-methoxyphenyl)-2-furanthiocarboxamide) are prepared and characterized by the NMR spectroscopy in solution; molecular and crystal structures in the solid state have been determined by X-ray single crystal diffractometry and the structures in the gas phase by DFT and AM1 calculations. The investigation is carried out in order to establish supramolecular amide and thioamide synthons of hydrogen bonding patterns in these G. Pavlović ( ) · V. Tralić-Kulenović

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Section: Crystal Structures Descriptionmentioning

confidence: 97%

Supramolecular amide and thioamide synthons in hydrogen bonding patterns of N-aryl-furamides and N-aryl-thiofuramides

et al. 2006

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“…The IR spectrum of a polycrystalline sample of (I) (Michta et al, 2008), N-methylthioacetamide (Flakus et al, 2007), N-(2-hydroxyethyl)-2-thiofuramide (Galešić et al, 1987) or N-(m-tolyl)thioacetamide (Ś miszek-Lindertet et al, 2007a). The value of the C S bond length of 1.61 Å is cited in the literature as representing 100% double-bond character, e.g.…”

Section: Figurementioning

confidence: 99%

3′-Methylacetanilide andN-benzylthioacetamide at low temperature

et al. 2008

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Molecules of the title compounds, 3'-methylacetanilide [or N-(m-tolyl)acetamide], C(9)H(11)NO, (I), and N-benzylthioacetamide, C(9)H(11)NS, (II), are connected by a framework of intermolecular N-H...O and N-H...S hydrogen bonds, respectively, forming chains with the graph-set description C(4), which run along the b axis. Analyses of the crystal structures of (I) and (II) are helpful in the elucidation of a generation mechanism of the IR spectra of hydrogen-bonded molecular crystals. The correlation between the IR spectra of studied compounds and structural data is also discussed.

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Structure of N-(2-hydroxyethyl)-2-thiofuramide

Cited by 2 publications

References 8 publications

Supramolecular amide and thioamide synthons in hydrogen bonding patterns of N-aryl-furamides and N-aryl-thiofuramides

Supramolecular amide and thioamide synthons in hydrogen bonding patterns of N-aryl-furamides and N-aryl-thiofuramides

3′-Methylacetanilide andN-benzylthioacetamide at low temperature

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