Aromaticity of ring carbo-mers of [N]annulenes and [N]cycloalkanes.
Identifieur interne : 002A05 ( Main/Exploration ); précédent : 002A04; suivant : 002A06Aromaticity of ring carbo-mers of [N]annulenes and [N]cycloalkanes.
Auteurs : Alessandro Soncini [Belgique] ; Patrick W. Fowler ; Christine Lepetit ; Remi ChauvinSource :
- Physical chemistry chemical physics : PCCP [ 1463-9076 ] ; 2008.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Heterocyclic Compounds, Hydrocarbons, Cyclic.
- Electrons, Magnetics, Models, Chemical, Quantum Theory.
Abstract
Maps of current density induced by a perpendicular external magnetic field are calculated at the ipsocentric CTOCD-DZ/6-31G**//B3PW91/6-31G** level for ring carbo-mers of [N]-annulenes (closed-shell singlet states of C(3N)H, N = 3 to 7, with q = -1, 0, +1, 0, -1, respectively, and also the triplet ground state for N = 4) and of [N]-cycloalkanes (C(3N)H(qN), N = 3, 4, 5). Strong four-electron diatropic ring currents indicate conventional pi aromaticity for all the singlet and triplet carbo-[N]annulenes studied, with the exception of C(12)H(4), where instead the strong two-electron paratropic ring current is the signature of pi antiaromaticity. The carbo-[N]cycloalkanes (also known as [N]pericyclynes) show only localized pi currents, consistent with non-aromaticity. There is no indication of a 'homo-aromatic' ring current attributable to the in-plane pi orbitals of the inserted C2 units in any of the maps. Consequences for the interpretation of ELF (electron localisation function) populations are discussed.
DOI: 10.1039/b715389a
PubMed: 18259634
Affiliations:
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Fowler</name></author><author><name sortKey="Lepetit, Christine" sort="Lepetit, Christine" uniqKey="Lepetit C" first="Christine" last="Lepetit">Christine Lepetit</name></author><author><name sortKey="Chauvin, Remi" sort="Chauvin, Remi" uniqKey="Chauvin R" first="Remi" last="Chauvin">Remi Chauvin</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2008">2008</date><idno type="RBID">pubmed:18259634</idno><idno type="pmid">18259634</idno><idno type="doi">10.1039/b715389a</idno><idno type="wicri:Area/PubMed/Corpus">002123</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002123</idno><idno type="wicri:Area/PubMed/Curation">002123</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">002123</idno><idno type="wicri:Area/PubMed/Checkpoint">002013</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">002013</idno><idno type="wicri:Area/Ncbi/Merge">000583</idno><idno type="wicri:Area/Ncbi/Curation">000583</idno><idno type="wicri:Area/Ncbi/Checkpoint">000583</idno><idno type="wicri:doubleKey">1463-9076:2008:Soncini A:aromaticity:of:ring</idno><idno type="wicri:Area/Main/Merge">002A31</idno><idno type="wicri:Area/Main/Curation">002A05</idno><idno type="wicri:Area/Main/Exploration">002A05</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Aromaticity of ring carbo-mers of [N]annulenes and [N]cycloalkanes.</title><author><name sortKey="Soncini, Alessandro" sort="Soncini, Alessandro" uniqKey="Soncini A" first="Alessandro" last="Soncini">Alessandro Soncini</name><affiliation wicri:level="4"><nlm:affiliation>Laboratory of Quantum Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, B-3001, Heverlee-Leuven, Belgium.</nlm:affiliation><country xml:lang="fr">Belgique</country><wicri:regionArea>Laboratory of Quantum Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, B-3001, Heverlee-Leuven</wicri:regionArea><orgName type="university">Katholieke Universiteit Leuven</orgName><placeName><settlement type="city">Louvain</settlement><region>Région flamande</region><region type="district" nuts="2">Province du Brabant flamand</region></placeName></affiliation></author><author><name sortKey="Fowler, Patrick W" sort="Fowler, Patrick W" uniqKey="Fowler P" first="Patrick W" last="Fowler">Patrick W. Fowler</name></author><author><name sortKey="Lepetit, Christine" sort="Lepetit, Christine" uniqKey="Lepetit C" first="Christine" last="Lepetit">Christine Lepetit</name></author><author><name sortKey="Chauvin, Remi" sort="Chauvin, Remi" uniqKey="Chauvin R" first="Remi" last="Chauvin">Remi Chauvin</name></author></analytic><series><title level="j">Physical chemistry chemical physics : PCCP</title><idno type="ISSN">1463-9076</idno><imprint><date when="2008" type="published">2008</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Electrons</term><term>Heterocyclic Compounds (chemistry)</term><term>Hydrocarbons, Cyclic (chemistry)</term><term>Magnetics</term><term>Models, Chemical</term><term>Quantum Theory</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Composés hétérocycliques ()</term><term>Hydrocarbures cycliques ()</term><term>Magnétisme</term><term>Modèles chimiques</term><term>Théorie quantique</term><term>Électrons</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Heterocyclic Compounds</term><term>Hydrocarbons, Cyclic</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Electrons</term><term>Magnetics</term><term>Models, Chemical</term><term>Quantum Theory</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Composés hétérocycliques</term><term>Hydrocarbures cycliques</term><term>Magnétisme</term><term>Modèles chimiques</term><term>Théorie quantique</term><term>Électrons</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Maps of current density induced by a perpendicular external magnetic field are calculated at the ipsocentric CTOCD-DZ/6-31G**//B3PW91/6-31G** level for ring carbo-mers of [N]-annulenes (closed-shell singlet states of C(3N)H, N = 3 to 7, with q = -1, 0, +1, 0, -1, respectively, and also the triplet ground state for N = 4) and of [N]-cycloalkanes (C(3N)H(qN), N = 3, 4, 5). Strong four-electron diatropic ring currents indicate conventional pi aromaticity for all the singlet and triplet carbo-[N]annulenes studied, with the exception of C(12)H(4), where instead the strong two-electron paratropic ring current is the signature of pi antiaromaticity. The carbo-[N]cycloalkanes (also known as [N]pericyclynes) show only localized pi currents, consistent with non-aromaticity. There is no indication of a 'homo-aromatic' ring current attributable to the in-plane pi orbitals of the inserted C2 units in any of the maps. Consequences for the interpretation of ELF (electron localisation function) populations are discussed.</div></front></TEI><affiliations><list><country><li>Belgique</li></country><region><li>Province du Brabant flamand</li><li>Région flamande</li></region><settlement><li>Louvain</li></settlement><orgName><li>Katholieke Universiteit Leuven</li></orgName></list><tree><noCountry><name sortKey="Chauvin, Remi" sort="Chauvin, Remi" uniqKey="Chauvin R" first="Remi" last="Chauvin">Remi Chauvin</name><name sortKey="Fowler, Patrick W" sort="Fowler, Patrick W" uniqKey="Fowler P" first="Patrick W" last="Fowler">Patrick W. Fowler</name><name sortKey="Lepetit, Christine" sort="Lepetit, Christine" uniqKey="Lepetit C" first="Christine" last="Lepetit">Christine Lepetit</name></noCountry><country name="Belgique"><region name="Région flamande"><name sortKey="Soncini, Alessandro" sort="Soncini, Alessandro" uniqKey="Soncini A" first="Alessandro" last="Soncini">Alessandro Soncini</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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