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https://hdl.handle.net/1959.11/9303
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DC Field | Value | Language |
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dc.contributor.author | Glover, Stephen | en |
dc.contributor.author | White, Jonathan M | en |
dc.contributor.author | Rosser, Adam Andrew | en |
dc.contributor.author | Digianantonio, Katherine M | en |
dc.date.accessioned | 2012-01-25T11:52:00Z | - |
dc.date.issued | 2011 | - |
dc.identifier.citation | The Journal of Organic Chemistry, 76(23), p. 9757-9763 | en |
dc.identifier.issn | 1520-6904 | en |
dc.identifier.issn | 0022-3263 | en |
dc.identifier.uri | https://hdl.handle.net/1959.11/9303 | - |
dc.description.abstract | The first X-ray structures of two anomeric N,N-dialkoxyamides (2 and 3) have been obtained, which confirm that they are highly pyramidalized at nitrogen and have long N-CO bonds, a characteristic of other anomeric amides and a consequence of drastically reduced amidicity. The crystals also demonstrate chirality at the amide nitrogen in the solid state. The structures are well-predicted by density functional calculations using N,N-dimethoxyacetamide as a model. The amidicity of N,N-dimethoxyacetamide has been estimated by two independent methods, COSNAR and a new transamidation method, which give almost identical resonance stabilization energies of -8.6 kcal mol⁻¹ and only 47% that of N,N-dimethylacetamide computed at the same level. The total destabilization is composed of a resonance and an inductive contribution, which we have evaluated separately. The electronegative oxygens at nitrogen are responsible for localization of the nitrogen lone pair on the amide nitrogen, a factor that contributes to a loss of resonance over and above the impact of pyramidalization at nitrogen, as well as the fact that N,N-dimethoxyacetamide is predicted to protonate on the carbonyl oxygen in preference to nitrogen. | en |
dc.language | en | en |
dc.publisher | American Chemical Society | en |
dc.relation.ispartof | The Journal of Organic Chemistry | en |
dc.title | Structures of N,N-Dialkoxyamides: Pyramidal Anomeric Amides with Low Amidicity | en |
dc.type | Journal Article | en |
dc.identifier.doi | 10.1021/jo201856u | en |
dc.subject.keywords | Structural Chemistry and Spectroscopy | en |
dc.subject.keywords | Theoretical and Computational Chemistry | en |
dc.subject.keywords | Physical Organic Chemistry | en |
local.contributor.firstname | Stephen | en |
local.contributor.firstname | Jonathan M | en |
local.contributor.firstname | Adam Andrew | en |
local.contributor.firstname | Katherine M | en |
local.subject.for2008 | 030799 Theoretical and Computational Chemistry not elsewhere classified | en |
local.subject.for2008 | 030606 Structural Chemistry and Spectroscopy | en |
local.subject.for2008 | 030505 Physical Organic Chemistry | en |
local.subject.seo2008 | 970103 Expanding Knowledge in the Chemical Sciences | en |
local.profile.school | School of Science and Technology | en |
local.profile.school | Chemistry | en |
local.profile.school | School of Science and Technology | en |
local.profile.school | Chemistry | en |
local.profile.email | sglover@une.edu.au | en |
local.profile.email | whitejm@unimelb.edu.au | en |
local.profile.email | arosser3@une.edu.au | en |
local.profile.email | kdigiana@princeton.edu | en |
local.output.category | C1 | en |
local.record.place | au | en |
local.record.institution | University of New England | en |
local.identifier.epublicationsrecord | une-20111116-082313 | en |
local.publisher.place | United States of America | en |
local.format.startpage | 9757 | en |
local.format.endpage | 9763 | en |
local.identifier.scopusid | 82255170733 | en |
local.peerreviewed | Yes | en |
local.identifier.volume | 76 | en |
local.identifier.issue | 23 | en |
local.title.subtitle | Pyramidal Anomeric Amides with Low Amidicity | en |
local.contributor.lastname | Glover | en |
local.contributor.lastname | White | en |
local.contributor.lastname | Rosser | en |
local.contributor.lastname | Digianantonio | en |
dc.identifier.staff | une-id:sglover | en |
dc.identifier.staff | une-id:arosser3 | en |
local.profile.orcid | 0000-0002-9344-8669 | en |
local.profile.orcid | 0000-0002-4123-7704 | en |
local.profile.role | author | en |
local.profile.role | author | en |
local.profile.role | author | en |
local.profile.role | author | en |
local.identifier.unepublicationid | une:9494 | en |
dc.identifier.academiclevel | Academic | en |
dc.identifier.academiclevel | Academic | en |
local.title.maintitle | Structures of N,N-Dialkoxyamides | en |
local.output.categorydescription | C1 Refereed Article in a Scholarly Journal | en |
local.search.author | Glover, Stephen | en |
local.search.author | White, Jonathan M | en |
local.search.author | Rosser, Adam Andrew | en |
local.search.author | Digianantonio, Katherine M | en |
local.uneassociation | Unknown | en |
local.identifier.wosid | 000297274800023 | en |
local.year.published | 2011 | en |
Appears in Collections: | Journal Article School of Science and Technology |
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