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dc.creatorMascavage, Linda M.
dc.creatorTierney, John
dc.creatorSonnet, Philip E.
dc.creatorDalton, David R.
dc.date.accessioned2021-04-16T14:35:09Z
dc.date.available2021-04-16T14:35:09Z
dc.date.issued2010-09-10
dc.identifier.citationL. M. Mascavage, J. Tierney, P. E. Sonnet and D. R. Dalton, “The Hoffmann-Schiff dichotomy: on the reaction between chloral and amines”, ARKIVOC (2010) viii: 278-284. https://doi.org/10.3998/ark.5550190.0011.819
dc.identifier.issn1551-7004
dc.identifier.doihttp://dx.doi.org/10.34944/dspace/6291
dc.identifier.urihttp://hdl.handle.net/20.500.12613/6309
dc.description.abstractIn the nearly two centuries since the discovery of chloral (2,2,2-trichloroacetaldehyde), numerous nitrogenous reactants have been used to generate products resulting from attack at the carbonyl group by nitrogen. The resulting tetrahedral species, a carbinolamine, is often unstable and has been reported to lose water to produce an imine as well as to lose chloroform to produce an amide. We find that the path, and hence the product, is a function of the electron density at the nitrogen of the reacting amine. The weaker arylamines produce imine whilst the more strongly basic alkylamines produce amide.
dc.format.extent7 pages
dc.languageEnglish
dc.language.isoeng
dc.relation.ispartofFaculty/ Researcher Works
dc.relation.haspartARKIVOC, Issue in Honor of Drs. Cynthia A. and Bruce E. Maryanoff
dc.relation.isreferencedbyARKAT USA
dc.rightsAttribution CC BY
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subjectAb initio calculations
dc.subjectBasicity
dc.subjectAldehydes
dc.subjectAmines
dc.subjectDensity functional calculations
dc.titleThe Hoffmann-Schiff dichotomy: on the reaction between chloral and amines
dc.typeText
dc.type.genreJournal article
dc.description.departmentChemistry
dc.relation.doihttps://doi.org/10.3998/ark.5550190.0011.819
dc.ada.noteFor Americans with Disabilities Act (ADA) accommodation, including help with reading this content, please contact scholarshare@temple.edu
dc.description.schoolcollegeTemple University. College of Science and Technology
dc.temple.creatorSonnet, Philip E.
dc.temple.creatorDalton, David R.
refterms.dateFOA2021-04-16T14:35:09Z


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