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Structure and packing of aminoxyl and piperidinyl acrylamide monomers
Author(s) -
Goswami Shailesh K.,
Hanton Lyall R.,
McAdam C. John,
Moratti Stephen C.,
Simpson Jim
Publication year - 2015
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229615015946
Subject(s) - chemistry , monomer , hydrogen bond , amide , piperidine , molecule , acrylamide , crystallography , solvent , polymer chemistry , acceptor , polymer , stereochemistry , organic chemistry , physics , condensed matter physics
The closely related title compounds, 4‐acrylamido‐2,2,6,6‐tetramethylpiperidine‐1‐oxyl, C 12 H 21 N 2 O 2 , (I), and N ‐(2,2,6,6‐tetramethylpiperidin‐4‐yl)acrylamide monohydrate, C 12 H 22 N 2 O·H 2 O, (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 R 2 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.