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dc.contributor.authorHealy, PC
dc.contributor.authorLoughlin, WA
dc.contributor.authorMcCleary, MA
dc.contributor.authorPierens, GK
dc.contributor.authorRowen, CC
dc.date.accessioned2017-05-03T12:22:41Z
dc.date.available2017-05-03T12:22:41Z
dc.date.issued2002
dc.date.modified2009-08-21T06:38:58Z
dc.identifier.issn0894-3230
dc.identifier.doi10.1002/poc.542
dc.identifier.urihttp://hdl.handle.net/10072/7030
dc.description.abstractThe structures of a series of sulfonylbicyclo[n.2.0]alkan-1-ols (n = 3-6) 1-6 were determined by single-crystal x-ray diffraction. A survey of the Cambridge Structural Database and Monte Carlo conformational searches using MacroModel were performed. Compounds 1, 3 and 4 show intramolecular hydrogen bonding. Compound 2 is stabilized by three-centered bifurcated intra- and intermolecular hydrogen bonds between the hydroxyl proton and the sulfone oxygens. Compounds 5 and 6 are stabilized by intermolecular hydrogen bonds formed between the trans 1-hydroxy and sulfonyl moieties. In compounds 1-6, the degree of cyclotorsion of the four- five-, six-, seven- and eight-membered rings adjacent to the bond between the bridgehead atoms C1 and C4 is reflected in the magnitude about the exterior angles about C1 (C2 - C1 - Cx) and C4 (C3 - C4 - C5). The six-membered ring systems of 2, 5 and 6 showed noteworthy increases in the C5 - C4 - C1 - Cx and C3 - C4 - C1 - C2 torsion angles, and this was attributed to the conformational constraints of the pseudo-chair conformation of the six-membered ring. Similar conformational structure effects were observed in the modeled structures 1a-6a to those observed for the x-ray structures 1-6.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherJohn Wiley and Sons, Ltd
dc.publisher.placeUK
dc.publisher.urihttps://onlinelibrary.wiley.com/doi/10.1002/poc.542
dc.relation.ispartofpagefrom733
dc.relation.ispartofpageto741
dc.relation.ispartofjournalJournal of Physical Organic Chemistry
dc.relation.ispartofvolume15
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchPhysical chemistry
dc.subject.fieldofresearchTheoretical and computational chemistry
dc.subject.fieldofresearchcode3405
dc.subject.fieldofresearchcode3406
dc.subject.fieldofresearchcode3407
dc.titleStructural studies on sulfonylbicyclo[n.2.0]alkan-1-ols
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.rights.copyright© 2002 John Wiley & Sons, Ltd. Self-archiving of the author-manuscript version is not yet supported by this publisher. Please refer to the journal link for access to the definitive, published version or contact the author for more information.
gro.date.issued2002
gro.hasfulltextNo Full Text
gro.griffith.authorHealy, Peter C.
gro.griffith.authorLoughlin, Wendy A.


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