dc.creator |
Bertolasi, Valerio |
|
dc.creator |
Gilli, Paola |
|
dc.creator |
Ferretti, Valeria |
|
dc.creator |
Gilli, Gastone |
|
dc.creator |
Vaughan, Keith, 1943- |
|
dc.creator |
Jollimore, Jason V. |
|
dc.date.accessioned |
2015-01-26T19:29:34Z |
|
dc.date.available |
2015-01-26T19:29:34Z |
|
dc.date.issued |
1999 |
|
dc.identifier.issn |
0108-7681 |
|
dc.identifier.issn |
1600-5740 |
|
dc.identifier.uri |
http://library2.smu.ca/xmlui/handle/01/25933 |
|
dc.description |
Publisher's version/PDF |
en_CA |
dc.description.abstract |
The crystal structures of six anti-[beta]-ketoarylhydrazones are reported: (a1) (E)-2-(4-cyanophenylhydrazono)-3-oxobutanenitrile; (a2) (E)-2-(4-methylphenylhydrazono)-3-oxobutanenitrile; (a3) (E)-2-(4-acetylphenylhydrazono)-3-oxobutanenitrile; (a4) (E)-2-(2-methoxyphenylhydrazono)-3-oxobutanenitrile; (a5) (E)-2-(2-acetylphenylhydrazono)-3-oxobutanenitrile; (a6) (E)-2-(2-nitrophenylhydrazono)-3-oxobutanenitrile. All compounds contain the [pi]-conjugated heterodienic group HN-N=C-C=O and could form, at least in principle, chains of intermolecular N-H...O hydrogen bonds assisted by resonance (RAHB-inter). Compounds (a1) and (a2) form this kind of hydrogen bond though with rather long N...O distances of 2.948 (3) and 2.980 (2) [Angstrom], and compound (a6) undergoes the same interaction but even more weakened [N...O 3.150 (1) [Angstrom] by the intramolecular bifurcation of the hydrogen bond donated by the N-H group. The intrinsic weakness of the intermolecular RAHB makes possible the setting up of alternative packing arrangements that are controlled by an antiparallel dipole-dipole (DD) interaction between two C=O groups of the [beta]-ketohydrazone moiety [compounds (a4) and (a5)]. The critical factors that cause the switching between the different packings turn out to be the presence of hydrogen bonding accepting substituents on the phenyl and, most frequently, the intramolecular N-H...O bond with the O atom of the phenyl o-substituent. The crystal packing is widely determined by RAHB-inter (three cases) or DD (two cases) interactions. Only compound (a3) displays a different packing arrangement, where the DD interaction is complemented by a non-resonant hydrogen bond between a p-acetyl phenyl substituent and the hydrazone N-H group [N...O 2.907 (2) [Angstrom]]. Crystal densities range from 1.24 to 1.44 Mg m[superscript -3] and are shown to increase with the number of intermolecular hydrogen bonds and other non-van der Waals interactions. |
en_CA |
dc.description.provenance |
Submitted by Janine Mills (janine.mills@smu.ca) on 2015-01-26T19:29:34Z
No. of bitstreams: 1
Vaughan_Keith_article_1999_a.pdf: 187099 bytes, checksum: a4ad0f46311c3c004ee52ed10528ddff (MD5) |
en |
dc.description.provenance |
Made available in DSpace on 2015-01-26T19:29:34Z (GMT). No. of bitstreams: 1
Vaughan_Keith_article_1999_a.pdf: 187099 bytes, checksum: a4ad0f46311c3c004ee52ed10528ddff (MD5)
Previous issue date: 1999 |
en |
dc.language.iso |
en |
en_CA |
dc.publisher |
International Union of Crystallography |
en_CA |
dc.relation.uri |
http://dx.doi.org/10.1107/S0108768199008435 |
|
dc.subject.lcsh |
Hydrazones |
|
dc.subject.lcsh |
Hydrogen bonding |
|
dc.title |
Interplay of hydrogen bonding and other molecular interactions in determining the crystal packing of a series of anti-[beta]-ketoarylhydrazones |
en_CA |
dc.type |
Text |
en_CA |
dcterms.bibliographicCitation |
Acta Crystallographica B55, 994-1004. (1999) |
en_CA |