Crystal Structures of Acrylamide Derivatives : N-t-Butylacrylamide, N-t-Butylmethacrylamide, Dimorphs of N-Phenylmethacrylamide, and N-o-Chlorophenylmethacrylamide

Kashino, Setsuo; Iwamoto, T.; Yamamoto, Etsuko; Shiraga, Tsuyoshi

doi:10.1246/bcsj.67.1226

Cited by 6 publications

(3 citation statements)

References 7 publications

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“…Similar chain propagation with the formation of six-membered rings has been observed for other acrylamide structures, i.e. N-[1,3-dihydroxy-2-(hydroxymethyl)propan-2yl]acrylamic acid (CSD refcode YOXBAO; Oddon et al, 1995) and N-tert-butylacrylamide (CEDXUE01; Kashino et al, 1994)]. However, in these examples, the rings form between near-orthogonal molecules (the dihedral angles between ring motifs are 104.35 for YOXBAO and 107.44 for CED-XUE01).…”

Section: Packing For (I)supporting

confidence: 70%

Structure and packing of aminoxyl and piperidinyl acrylamide monomers

et al. 2015

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The closely related title compounds, 4-acrylamido-2,2,6,6-tetramethylpiperidine-1-oxyl, C12H21N2O2, (I), and N-(2,2,6,6-tetramethylpiperidin-4-yl)acrylamide monohydrate, C12H22N2O·H2O, (II), are important monomers in the preparation of redox-active polymers. They comprise an acrylamide group of the usual s-cis configuration appended to a 2,2,6,6-tetramethyl-substituted piperidine-1-oxyl radical or a piperidinyl chair, respectively. The adjacent amide and piperidinyl H atoms are approximately trans across the C-N bond. The packing in (I) is dominated by N-H...O hydrogen bonds; these are supported by C-H...O contacts to form an R2(1)(6) ring repeat, a motif which has been observed in other acrylamide structures. In (II), hydrogen bonds are again key to the packing arrangements. In this case, the incorporated solvent water molecule acts as an acceptor through its O atom and as a donor through both H atoms, binding three adjacent piperidinylacrylamide molecules into layers. In both structures, weak C-H...O contacts involving the piperidinyl methyl H atoms and a proximal acrylamide carbonyl O atom extend the structure in the third dimension.

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Section: Packing For (I)supporting

confidence: 70%

Structure and packing of aminoxyl and piperidinyl acrylamide monomers

et al. 2015

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“…The compound was obtained as a by-product in the preparation of N-o-chlorophenylmethacrylamide (Kashino et al, 1994) by the method described by James & Ciotti (1955). The crystals were grown from a benzene solution of the reaction mixture by slow evaporation.…”

Section: Methodsmentioning

confidence: 99%

N-Phenylsulfonyl-N-o-chlorophenylmethacrylamide, C16H14ClNO3S

Shiraga¹,

Iwamoto²,

Kashino³

1995

Acta Crystallogr C

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“…The N(1)-C (11) bond length in the title compound 1 is 1.34 A ˚as observed in other amides (1.32-1.35 A ˚). 12 The C( 10 bond and C-CH 3 bond lengths (Fig. 1a).…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Self-assembly of methacrylamides assisted by an interplay of N–H⋯O, C–H⋯O, C–H⋯π and π–π interactions

2004

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Solid state self-assembly of methacrylamides (1-3) with intermolecular N-H … O and C-H … O hydrogen bonds are discussed. Interesting structures in the crystal lattice of 1 and 2 are ascribed to the aromatic surfaces that are orthogonal and twisted to each other along the hydrogen bonded chains. In addition, an interconnected network of face-to-face (p … p) and edge-to-face (C-H … p) interactions have been observed which are cooperative in nature. Compound 3 showed a staggered packing of adamantane groups along the H-bonded chains. In all three structures, the self-assembly was facilitated by strong hydrogen bonding, p … p interactions and packing forces involving bulky groups.

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Crystal Structures of Acrylamide Derivatives : N-t-Butylacrylamide, N-t-Butylmethacrylamide, Dimorphs of N-Phenylmethacrylamide, and N-o-Chlorophenylmethacrylamide

Cited by 6 publications

References 7 publications

Structure and packing of aminoxyl and piperidinyl acrylamide monomers

Structure and packing of aminoxyl and piperidinyl acrylamide monomers

N-Phenylsulfonyl-N-o-chlorophenylmethacrylamide, C16H14ClNO3S

Self-assembly of methacrylamides assisted by an interplay of N–H⋯O, C–H⋯O, C–H⋯π and π–π interactions

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