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Substituent-dependent negative hyperconjugation in 2-aryl-1,3-N,N-heterocycles. Fine-tuned anomeric effect?
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The epimerization reactions of conformationally inflexible 2-aryl-1,3-N,N-heterocycles were used as model systems to study the role of the nitrogen lone pair-C2 associated antibonding orbital hyperconjugative interactions in the experimentally observed substituent-dependent generalized anomeric effect. The measured reaction free enthalpies were found to correlate well with the sum of the hyperconjugative stabilization energies of all the vicinal donor-acceptor orbital overlaps around C2, obtained from ab initio NBO analysis, and both quantities correlated linearly with the Hammett-Brown substituent constant. The individual stereoelectronic interactions (n(N)-sigma*(C2-N), n(N)-sigma*(C2-Ar), n(N-sigma)*(C2-H)) were also observed to exhibit a substituent dependence, despite their distance from the 2-aryl substituent and their nonperiplanar arrangement. The higher the electron-withdrawing effect of the 2-aryl substituent, the larger was the stabilization for n(N)-sigma*(C2-Ar), while the overlaps n(N)-sigma*(C2-N) and n(N)-sigma*(C2-H) changed in the opposite sense. The different polarization of the acceptor sigma* orbitals, caused by the 2-aryl substituent, accounted for the observed propagation of the substituent effect. These results promote a detailed explanation of the useful tautomeric behavior of the 2-aryl-1,3-X,N-heterocycles, and reveal the nature of the connection between the anomeric effect and the Hammett-type linear free energy relationship.
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<div class="JournalArticle Publication short-list"> <div class="authors"> <span class="author-name" mtid="10001147"> <a href="/gui2/?type=authors&mode=browse&sel=10001147" target="_blank">Hetenyi, A N</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10001168"> <a href="/gui2/?type=authors&mode=browse&sel=10001168" target="_blank">Martinek, T A</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10002383"> <a href="/gui2/?type=authors&mode=browse&sel=10002383" target="_blank">Lazar, L</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="10012454"> <a href="/gui2/?type=authors&mode=browse&sel=10012454" target="_blank">Zalan, Z</a> </span> <span class="author-type"> </span> ; <span class="author-name" mtid="1381350"> <a href="/gui2/?type=authors&mode=browse&sel=1381350" target="_blank">Fulop, F</a> </span> <span class="author-type"> </span> </div ><div class="title"><a href="/gui2/?mode=browse¶ms=publication;1013527" mtid="1013527" target="_blank">Substituent-dependent negative hyperconjugation in 2-aryl-1,3-N,N-heterocycles. Fine-tuned anomeric effect?</a></div> <div class="pub-info"> <span class="journal-title">JOURNAL OF ORGANIC CHEMISTRY</span> <span class="journal-volume">68</span> : <span class="journal-issue">14</span> <span class="page"> pp. 5705-5712. , 8 p. </span> <span class="year">(2003)</span> </div> <div class="pub-end"><div class="identifier-list"> <span class="identifiers"> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="10.1021/jo034417" target="_blank" href="https://doi.org/10.1021/jo034417"> DOI </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="10.1021/jo034417+" target="_blank" href="https://doi.org/10.1021/jo034417%2B"> DOI </a> </span> <span class="id identifier oa_RESTRICTED" title=" Korlátozott "> <a style="color:black" title="36253" target="_blank" href="http://real.mtak.hu/36253"> REAL </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="000184060600033" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000184060600033"> WoS </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="0037662044" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-0037662044"> Scopus </a> </span> <span class="id identifier oa_none" title="none"> <a style="color:blue" title="12839466" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12839466&dopt=Abstract"> PubMed </a> </span> <span class="id identifier oa_RESTRICTED" title=" Korlátozott "> <a style="color:blue" title="7564" target="_blank" href="http://publicatio.bibl.u-szeged.hu/7564"> SZTE Publicatio </a> </span> </span> </div> <div class="short-pub-prop-list"> <span class="short-pub-mtid"> Közlemény:1013527 </span> <span class="status-holder"><span class="status-data status-VALIDATED"> Egyeztetett </span></span> <span class="pub-core">Forrás Idéző </span> <span class="pub-type">Folyóiratcikk (Szakcikk ) </span> <!-- && !record.category.scientific --> <span class="pub-category">Tudományos</span> <div class="publication-citation" style="margin-left: 0.5cm;"> <span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 42</span> | Független: 30 | Függő: 12 | Nem jelölt: 0 | WoS jelölt: 31 | Scopus jelölt: 33 | WoS/Scopus jelölt: 33 | DOI jelölt: 30 </div> </div> </div> </div><div class="JournalArticle Publication long-list">
<div class="authors">
<img title="Forrásközlemény" style="float: left" src="/frontend/resources/grid/publication-core-icon.png">
<img title="Idézőközlemény" style="float: left" src="/frontend/resources/grid/publication-citation-icon.png">
<div class="autype autype0"> <span class="author-name" mtid="10001147"><a
href="/gui2/?type=authors&mode=browse&sel=10001147" target="_blank">Hetenyi A N
(<span class="authorship-author-name">Hetényi Anasztázia</span>
<span class="authorAux-mtmt"> NMR spektroszkópia, molekulamodellezés</span>)
</a>
</span>
<span class="author-affil"><span title="Szegedi Tudományegyetem">SZTE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Gyógyszerkémiai Intézet</span>
;
<span class="author-name" mtid="10001168"><a
href="/gui2/?type=authors&mode=browse&sel=10001168" target="_blank">Martinek T A
(<span class="authorship-author-name">Martinek Tamás</span>
<span class="authorAux-mtmt"> Gyógyszerkémia</span>)
</a>
</span>
<span class="author-affil"><span title="Szegedi Tudományegyetem">SZTE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Gyógyszerkémiai Intézet</span>
;
<span class="author-name" mtid="10002383"><a
href="/gui2/?type=authors&mode=browse&sel=10002383" target="_blank">Lazar L
(<span class="authorship-author-name">Lázár László</span>
<span class="authorAux-mtmt"> Szerves kémia, gyógyszerkémia</span>)
</a>
</span>
<span class="author-affil"><span title="Szegedi Tudományegyetem">SZTE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Gyógyszerkémiai Intézet</span>
;
<span class="author-name" mtid="10012454"><a
href="/gui2/?type=authors&mode=browse&sel=10012454" target="_blank">Zalan Z
(<span class="authorship-author-name">Zalán Zita</span>
<span class="authorAux-mtmt"> Szerves kémia, gyógyszerkémia</span>)
</a>
</span>
<span class="author-affil"><span title="Szegedi Tudományegyetem">SZTE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Gyógyszerkémiai Intézet</span>
;
<span class="author-name" mtid="1381350"><a
href="/gui2/?type=authors&mode=browse&sel=1381350" target="_blank">Fulop F
(<span class="authorship-author-name">Fülöp Ferenc</span>
<span class="authorAux-mtmt"> Kémia</span>)
</a>
</span>
<span class="author-affil"><span title="Szegedi Tudományegyetem">SZTE</span>/<span title="Gyógyszerésztudományi Kar">GYTK</span>/Gyógyszerkémiai Intézet</span>
</div>
</div>
<div class="title"><a href="/gui2/?mode=browse¶ms=publication;1013527" target="_blank">Substituent-dependent negative hyperconjugation in 2-aryl-1,3-N,N-heterocycles. Fine-tuned anomeric effect?</a></div> <div> <span class="journal-title">JOURNAL OF ORGANIC CHEMISTRY</span>
<span class="journal-issn">(<a target="_blank" href="https://portal.issn.org/resource/ISSN/0022-3263">0022-3263</a> <a target="_blank" href="https://portal.issn.org/resource/ISSN/1520-6904">1520-6904</a>)</span>:
<span class="journal-volume">68</span> <span class="journal-issue">14</span>
<span class="page">
pp 5705-5712
</span> <span class="year">(2003)</span>
</div>
<div class="pub-footer">
<span class="language" xmlns="http://www.w3.org/1999/html">Nyelv:
Angol
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<span class="id identifier oa_none" title="none">
<a style="color:blue" title="10.1021/jo034417" target="_blank" href="https://doi.org/10.1021/jo034417">
DOI
</a>
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<span class="id identifier oa_none" title="none">
<a style="color:blue" title="10.1021/jo034417+" target="_blank" href="https://doi.org/10.1021/jo034417%2B">
DOI
</a>
</span>
<span class="id identifier oa_RESTRICTED" title=" Korlátozott
">
<a style="color:black" title="36253" target="_blank" href="http://real.mtak.hu/36253">
REAL
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<a style="color:blue" title="000184060600033" target="_blank" href="https://www.webofscience.com/wos/woscc/full-record/000184060600033">
WoS
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<a style="color:blue" title="0037662044" target="_blank" href="http://www.scopus.com/record/display.url?origin=inward&eid=2-s2.0-0037662044">
Scopus
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<a style="color:blue" title="12839466" target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12839466&dopt=Abstract">
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<a style="color:blue" title="7564" target="_blank" href="http://publicatio.bibl.u-szeged.hu/7564">
SZTE Publicatio
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<span title="Nyilvános idézőközlemények összesen, említések nélkül" class="citingPub-count">Nyilvános idéző összesen: 42</span>
| Független: 30
| Függő: 12
| Nem jelölt: 0
| WoS jelölt: 31
| Scopus jelölt: 33
| WoS/Scopus jelölt: 33
| DOI jelölt: 30
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<a target="_blank" href="/api/publication?cond=citations.related;eq;1013527&sort=publishedYear,desc&sort=title">
Idézett közlemények száma: 3
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<div class="mtid"><span class="long-pub-mtid">Közlemény: 1013527</span>
| <span class="status-data status-VALIDATED"> Egyeztetett
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<span class="oldId">Régi azonosító: 1013527</span> |
Forrás Idéző
| <span class="type-subtype">Folyóiratcikk
( Szakcikk
)
</span>
| <span class="pub-category">Tudományos</span>
| <span class="publication-sourceOfData">WOS</span>
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<div class="lastModified">Utolsó módosítás: 2022.07.13. 02:54 Áts József (admin)
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