Search for a Predicted Hydrogen Bonding Motif – A Multidisciplinary Investigation into the Polymorphism of 3-Azabicyclo[3.3.1]nonane-2,4-dione.
The predictions of the crystal structure of 3-azabicyclo[3.3.1]nonane-2,4-dione submitted in the 2001 international blind test of crystal structure prediction (CSP2001) led to the conclusion that crystal structures containing an alternative hydrogen bonded dimer motif were energetically competitive...
| Publicado en: | Journal of the American Chemical Society Vol. 129; no. 12; pp. 3649 - 3658 |
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| Autores principales: | , , , , , , , , , , , |
| Formato: | Artículo |
| Publicado: |
American Chemical Society
3/28/2007
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| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=24961709&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 24961709 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 3/28/2007 vid: 129 iid: 12 pid: 997 pub: American Chemical Society artinfo: ui: 24961709 10.1021/ja0687466 ppf: 3649 ppct: 9 formats: tig: atl: Search for a Predicted Hydrogen Bonding Motif – A Multidisciplinary Investigation into the Polymorphism of 3-Azabicyclo[3.3.1]nonane-2,4-dione. aug: au: Hulme, Ashley T. Johnston, Andrea Florence, Alastair J. Fernandes, Phillipe Shankland, Kenneth Bedford, Cohn T. Welch, Gareth W. A. Sadiq, Ghazala Haynes, Delia A. Samuel Motherwell, W. D. Tocher, Derek A. Price, Sarah L. affil: University College London University of Strathclyde CCLRC Rutherford Appleton Laboratory University of Manchester Cambridge Crystallographic Data Centre School of Chemistry, University of KwaZulu-Natal su: Hydrogen bonding Polymorphism (Crystallography) Solution (Chemistry) Diffraction patterns Dimers Fourier transform infrared spectroscopy Physical & theoretical chemistry research sug: subj: Hydrogen bonding Polymorphism (Crystallography) Solution (Chemistry) Diffraction patterns Dimers Fourier transform infrared spectroscopy Physical & theoretical chemistry research ab: The predictions of the crystal structure of 3-azabicyclo[3.3.1]nonane-2,4-dione submitted in the 2001 international blind test of crystal structure prediction (CSP2001) led to the conclusion that crystal structures containing an alternative hydrogen bonded dimer motif were energetically competitive with the known catemer-based structure. Here we report an extensive search for a dimer-based crystal structure. Using an automated polymorph screen a new catemer-based metastable polymorph (form 2) and two new catemer-based solvates were found, and concurrent thermal studies reproduced form 2 and identified a plastic phase (form 3), whose powder X-ray diffraction pattern was consistent with the cubic space group I2 (a = 7.5856(1) Å). Computational studies on the monomer showed that the imide NH was a weak hydrogen bond donor, rationalizing the occurrence of the plastic phase which involved the breaking of all hydrogen bonds, and modeling of small clusters showed that dimers could easily reorganize to give the catemer. FTIR spectra confirmed the weakness of the hydrogen bond, with the solute showing no self-assembly in solution. It is concluded that the weakness of the NH donor, coupled with the globular shape of the molecule, allows unusually facile transformation between alternative hydrogen bonding motifs during aggregation and nucleation. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2007 holdings: @attributes: islocal: N |
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