dc.creator |
Bertolasi, Valerio |
|
dc.creator |
Gilli, Paola |
|
dc.creator |
Ferretti, Valeria |
|
dc.creator |
Gilli, Gastone |
|
dc.creator |
Vaughan, Keith, 1943- |
|
dc.date.accessioned |
2014-11-17T15:45:07Z |
|
dc.date.available |
2014-11-17T15:45:07Z |
|
dc.date.issued |
1999 |
|
dc.identifier.issn |
1144-0546 |
|
dc.identifier.issn |
1369-9261 |
|
dc.identifier.uri |
http://library2.smu.ca/xmlui/handle/01/25909 |
|
dc.description |
Publisher's version/PDF |
en_CA |
dc.description.abstract |
The crystal structures of six [beta]-ketoarylhydrazones are reported: 1,(Z)-2-(2-bromophenylhydrazono)-3-oxobutanenitrile; 2, (Z)-2-(2-methylphenylhydrazono)-3-oxobutanenitrile; 3, (E)-methyl-2-(2-methoxyphenylhydrazono)-3-oxobutanoate; 4, E, methyl-2-(2-cyanophenylhydrazono)-3-oxobutanoate; 5, (Z)-methyl-2-(4-cyanophenylhydrazono)-3-oxobutanoate; 6, pentane-2,3,4-trione-3-(2-carboxyphenylhydrazone). All of them form intramolecular hydrogen bonds assisted by resonance (RAHB), with N...O distances in the range 2.541(5)-2.615(3) [Angstrom]. These hydrogen bonds are differently aff ected by the substituents at the heterodienic fragment, being strengthened by electronwithdrawing substituents in position 2 (more by 2-COMe than 2-CN substitution), and weakened in [beta]-esterhydrazones and when the N-H forms a bifurcated hydrogen bond. The role played by the different steric and electronic properties of the substituents in strengthening the H-bond is investigated, besides X-ray crystallography, by IR and [superscript 1]H NMR characterization of the NH proton, and quantum mechanical DFT calculations at the B3LYP/6-31 + G(d,p) level of theory on test molecules. |
en_CA |
dc.description.provenance |
Submitted by Janine Mills (janine.mills@smu.ca) on 2014-11-17T15:45:07Z
No. of bitstreams: 1
Vaughan_Keith_article_1999.pdf: 184586 bytes, checksum: fc3e1b316b760d8939740d07009d9079 (MD5) |
en |
dc.description.provenance |
Made available in DSpace on 2014-11-17T15:45:07Z (GMT). No. of bitstreams: 1
Vaughan_Keith_article_1999.pdf: 184586 bytes, checksum: fc3e1b316b760d8939740d07009d9079 (MD5)
Previous issue date: 1999 |
en |
dc.language.iso |
en |
en_CA |
dc.publisher |
Royal Society of Chemistry and the Centre National de la Recherche Scientifique |
en_CA |
dc.subject.lcsh |
Hydrogen bonding |
|
dc.title |
Interplay between steric and electronic factors in determining the strength of intramolecular resonance-assisted NH...O hydrogen bond in a series of [beta]-ketoarylhydrazones |
en_CA |
dc.type |
Text |
en_CA |
dcterms.bibliographicCitation |
New Journal of Chemistry 23, 1261-1267. (1999) |
en_CA |