Untitled

Strenge, Andrea; Rademacher, Paul

doi:10.1002/(sici)1099-0690(199907)1999:7<1611::aid-ejoc1611>3.3.co;2-1

Cited by 3 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The larger negative frequency shift for the methylthio derivative (1) in relation to the dimethylamino derivative (2) should be ascribed to the closer proximity of the empty '* CÐS orbital [AE 3 = 3.25 eV for MeSMe (Modelli et al, 1991)] to the unperturbed % C N(OH) orbital energy level [IE = 9.40 eV for C 6 H 10 C NOH (Strenge & Rademacher, 1999)] rather than to the proximity between the empty '* CÐN orbital [AE = 4.80 eV for Me 3 N (Giordan et al, 1985)] to the unperturbed % C N(OH) orbital. This effect originates stronger % C N /'* CÐX orbital interactions for (1) than (2), which in turn leads to a larger decrease of the C N bond order and thus in the # C N frequency of (1) with respect to (2).…”

Section: Figurementioning

confidence: 99%

Self-association and stereochemistry study of 2-methylthio-, 2-dimethylaminocyclohexanone oximes and the parent cyclohexanone oxime

Olivato

Ribeiro

Zukerman-Schpector

et al. 2001

Acta Crystallogr Sect B

View full text Add to dashboard Cite

X-ray diffraction analyses of 2-substituted cyclohexanone oximes C5H9(X)C=NOH [X = SMe (1), NMe2 (2)] and of the parent compound [X = H (3)] showed that their cyclohexyl rings are in a slightly distorted chair conformation. These compounds assume in the solid state the (E) configuration bearing the 2-substituents in the axial conformation. Compounds (1) and (2) exist as dimeric and polymeric hydrogen-bond associates, respectively. Low-temperature X-ray analysis of the cyclohexanone oxime (3) showed that the molecules are associated forming two independent trimers. The dimer in (1) and the trimer in (3) are built up via [O-H...N=C] hydrogen bonds, while the polymer of (2) is via the [OH...NMe2] hydrogen bond. The comparative IR nu(OH) and nu(C=N) analysis of the title compounds, in the solid state and in CCl4 solution, fully supports the nature of the associates for (1)-(3) obtained by X-ray diffraction. The IR azomethyne frequency shift analysis (Deltanu(C=N)) also suggests the occurrence of the pi(C=N)/sigma*(C-X) orbital interaction which stabilizes the axial conformations of (1) and (2).

show abstract

Section: Figurementioning

confidence: 99%

Self-association and stereochemistry study of 2-methylthio-, 2-dimethylaminocyclohexanone oximes and the parent cyclohexanone oxime

Olivato

Ribeiro

Zukerman-Schpector

et al. 2001

Acta Crystallogr Sect B

View full text Add to dashboard Cite

show abstract

“…In recent papers, the importance of the hydrogen bonding of oximes in the building of supramolecular architectures was highlighted. The versatility of the oxime system is due to the possibility of building dimers, trimers, tetramers, or polymers via hydrogen bonds (Chart ). , …”

mentioning

confidence: 99%

H-Bond-Driven Supramolecular Architectures of the Syn and Anti Isomers of the Dioxime of Bicyclo[3.3.1]nonane-3,7-dione

et al. 2009

View full text Add to dashboard Cite

The formation and high stability of the H-bond-driven supramolecular architectures of the syn and anti isomers of the dioxime of bicyclo[3.3.1]nonane-3,7-dione were investigated by single crystal X-ray diffraction, NMR, FTIR, and molecular modeling. Self-assembly of the achiral syn isomer into a cyclic trimer (supramolecular wheel) and of the chiral anti isomer into homochiral cyclic dimers was observed.

show abstract