Carbo-benzene's aromaticity, before and beyond: a tribute to Nozoe.
Identifieur interne : 001715 ( PubMed/Curation ); précédent : 001714; suivant : 001716Carbo-benzene's aromaticity, before and beyond: a tribute to Nozoe.
Auteurs : Kévin Cocq [France] ; Valérie Maraval ; Nathalie Saffon-Merceron ; Remi ChauvinSource :
- Chemical record (New York, N.Y.) [ 1528-0691 ] ; 2015.
Abstract
Beyond rigorous inspection of the literature, selected comments and drawings from the Nozoe Autograph Books show how concepts and targets of the chemistry of today already existed 40 years ago. This is illustrated for the chemistry of carbo-mers, which was actually unknowingly inspired by chemists of the golden age. After a personal travel through time and pages by the last author of this essay, who meets autographs by people who have been important in his career, in particular on the occasions of Nozoe's visits to France or past ISNA events, unpublished results in non-benzenoid chemistry are dedicated to Nozoe's memory. Experimental advances are first disclosed on the comparative chemistry of the three ortho, meta and para isomers of tetraphenyl-carbo-benzene C18 H2 Ph4 , the known ortho isomer serving as a reference. The two CH vertices of these chromophores make their [6]pericyclyne precursors quite sensitive and their yields and purifications challenging to optimize. The meta isomer was, however, isolated in 18% yield, and described by NMR and UV-vis absorption spectroscopy and crystallography. The para isomer was characterized both in pure form and in a 1:1 mixture with a single isomer of its HCl adduct, including by X-ray diffraction analysis of a co-crystal showing that the interior of the C18 ring of the HCl adduct is filled by the Cl atom. Theoretical advances are then offered regarding the "aromatic character" of a triple bond, by showing that the topological acyclic reference of acetylene is the Möbius-twisted cyclobutadiene. Acetylenoids are finally proposed as a novel class of non-benzenoid aromatics.
DOI: 10.1002/tcr.201402091
PubMed: 25630606
Links toward previous steps (curation, corpus...)
- to stream PubMed, to step Corpus: Pour aller vers cette notice dans l'étape Curation :001715
Links to Exploration step
pubmed:25630606Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Carbo-benzene's aromaticity, before and beyond: a tribute to Nozoe.</title>
<author><name sortKey="Cocq, Kevin" sort="Cocq, Kevin" uniqKey="Cocq K" first="Kévin" last="Cocq">Kévin Cocq</name>
<affiliation wicri:level="1"><nlm:affiliation>CNRS, Laboratoire de Chimie de Coordination (LCC), 205 route de Narbonne, BP 44099, F-31077, Toulouse, France; Université de Toulouse, UPS, Institut de Chimie de Toulouse, ICT-FR2599, 118 route de Narbonne, F-31062, Toulouse, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>CNRS, Laboratoire de Chimie de Coordination (LCC), 205 route de Narbonne, BP 44099, F-31077, Toulouse, France; Université de Toulouse, UPS, Institut de Chimie de Toulouse, ICT-FR2599, 118 route de Narbonne, F-31062, Toulouse</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Maraval, Valerie" sort="Maraval, Valerie" uniqKey="Maraval V" first="Valérie" last="Maraval">Valérie Maraval</name>
</author>
<author><name sortKey="Saffon Merceron, Nathalie" sort="Saffon Merceron, Nathalie" uniqKey="Saffon Merceron N" first="Nathalie" last="Saffon-Merceron">Nathalie Saffon-Merceron</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="2015">2015</date>
<idno type="RBID">pubmed:25630606</idno>
<idno type="pmid">25630606</idno>
<idno type="doi">10.1002/tcr.201402091</idno>
<idno type="wicri:Area/PubMed/Corpus">001715</idno>
<idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">001715</idno>
<idno type="wicri:Area/PubMed/Curation">001715</idno>
<idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">001715</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en">Carbo-benzene's aromaticity, before and beyond: a tribute to Nozoe.</title>
<author><name sortKey="Cocq, Kevin" sort="Cocq, Kevin" uniqKey="Cocq K" first="Kévin" last="Cocq">Kévin Cocq</name>
<affiliation wicri:level="1"><nlm:affiliation>CNRS, Laboratoire de Chimie de Coordination (LCC), 205 route de Narbonne, BP 44099, F-31077, Toulouse, France; Université de Toulouse, UPS, Institut de Chimie de Toulouse, ICT-FR2599, 118 route de Narbonne, F-31062, Toulouse, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>CNRS, Laboratoire de Chimie de Coordination (LCC), 205 route de Narbonne, BP 44099, F-31077, Toulouse, France; Université de Toulouse, UPS, Institut de Chimie de Toulouse, ICT-FR2599, 118 route de Narbonne, F-31062, Toulouse</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Maraval, Valerie" sort="Maraval, Valerie" uniqKey="Maraval V" first="Valérie" last="Maraval">Valérie Maraval</name>
</author>
<author><name sortKey="Saffon Merceron, Nathalie" sort="Saffon Merceron, Nathalie" uniqKey="Saffon Merceron N" first="Nathalie" last="Saffon-Merceron">Nathalie Saffon-Merceron</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">Chemical record (New York, N.Y.)</title>
<idno type="eISSN">1528-0691</idno>
<imprint><date when="2015" type="published">2015</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass></textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">Beyond rigorous inspection of the literature, selected comments and drawings from the Nozoe Autograph Books show how concepts and targets of the chemistry of today already existed 40 years ago. This is illustrated for the chemistry of carbo-mers, which was actually unknowingly inspired by chemists of the golden age. After a personal travel through time and pages by the last author of this essay, who meets autographs by people who have been important in his career, in particular on the occasions of Nozoe's visits to France or past ISNA events, unpublished results in non-benzenoid chemistry are dedicated to Nozoe's memory. Experimental advances are first disclosed on the comparative chemistry of the three ortho, meta and para isomers of tetraphenyl-carbo-benzene C18 H2 Ph4 , the known ortho isomer serving as a reference. The two CH vertices of these chromophores make their [6]pericyclyne precursors quite sensitive and their yields and purifications challenging to optimize. The meta isomer was, however, isolated in 18% yield, and described by NMR and UV-vis absorption spectroscopy and crystallography. The para isomer was characterized both in pure form and in a 1:1 mixture with a single isomer of its HCl adduct, including by X-ray diffraction analysis of a co-crystal showing that the interior of the C18 ring of the HCl adduct is filled by the Cl atom. Theoretical advances are then offered regarding the "aromatic character" of a triple bond, by showing that the topological acyclic reference of acetylene is the Möbius-twisted cyclobutadiene. Acetylenoids are finally proposed as a novel class of non-benzenoid aromatics. </div>
</front>
</TEI>
<pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">25630606</PMID>
<DateCompleted><Year>2015</Year>
<Month>05</Month>
<Day>21</Day>
</DateCompleted>
<DateRevised><Year>2015</Year>
<Month>02</Month>
<Day>18</Day>
</DateRevised>
<Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1528-0691</ISSN>
<JournalIssue CitedMedium="Internet"><Volume>15</Volume>
<Issue>1</Issue>
<PubDate><Year>2015</Year>
<Month>Feb</Month>
</PubDate>
</JournalIssue>
<Title>Chemical record (New York, N.Y.)</Title>
<ISOAbbreviation>Chem Rec</ISOAbbreviation>
</Journal>
<ArticleTitle>Carbo-benzene's aromaticity, before and beyond: a tribute to Nozoe.</ArticleTitle>
<Pagination><MedlinePgn>347-61</MedlinePgn>
</Pagination>
<ELocationID EIdType="doi" ValidYN="Y">10.1002/tcr.201402091</ELocationID>
<Abstract><AbstractText>Beyond rigorous inspection of the literature, selected comments and drawings from the Nozoe Autograph Books show how concepts and targets of the chemistry of today already existed 40 years ago. This is illustrated for the chemistry of carbo-mers, which was actually unknowingly inspired by chemists of the golden age. After a personal travel through time and pages by the last author of this essay, who meets autographs by people who have been important in his career, in particular on the occasions of Nozoe's visits to France or past ISNA events, unpublished results in non-benzenoid chemistry are dedicated to Nozoe's memory. Experimental advances are first disclosed on the comparative chemistry of the three ortho, meta and para isomers of tetraphenyl-carbo-benzene C18 H2 Ph4 , the known ortho isomer serving as a reference. The two CH vertices of these chromophores make their [6]pericyclyne precursors quite sensitive and their yields and purifications challenging to optimize. The meta isomer was, however, isolated in 18% yield, and described by NMR and UV-vis absorption spectroscopy and crystallography. The para isomer was characterized both in pure form and in a 1:1 mixture with a single isomer of its HCl adduct, including by X-ray diffraction analysis of a co-crystal showing that the interior of the C18 ring of the HCl adduct is filled by the Cl atom. Theoretical advances are then offered regarding the "aromatic character" of a triple bond, by showing that the topological acyclic reference of acetylene is the Möbius-twisted cyclobutadiene. Acetylenoids are finally proposed as a novel class of non-benzenoid aromatics. </AbstractText>
<CopyrightInformation>Copyright © 2014 The Chemical Society of Japan and Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</CopyrightInformation>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Cocq</LastName>
<ForeName>Kévin</ForeName>
<Initials>K</Initials>
<AffiliationInfo><Affiliation>CNRS, Laboratoire de Chimie de Coordination (LCC), 205 route de Narbonne, BP 44099, F-31077, Toulouse, France; Université de Toulouse, UPS, Institut de Chimie de Toulouse, ICT-FR2599, 118 route de Narbonne, F-31062, Toulouse, France.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Maraval</LastName>
<ForeName>Valérie</ForeName>
<Initials>V</Initials>
</Author>
<Author ValidYN="Y"><LastName>Saffon-Merceron</LastName>
<ForeName>Nathalie</ForeName>
<Initials>N</Initials>
</Author>
<Author ValidYN="Y"><LastName>Chauvin</LastName>
<ForeName>Remi</ForeName>
<Initials>R</Initials>
</Author>
</AuthorList>
<Language>eng</Language>
<PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType>
</PublicationTypeList>
<ArticleDate DateType="Electronic"><Year>2015</Year>
<Month>01</Month>
<Day>29</Day>
</ArticleDate>
</Article>
<MedlineJournalInfo><Country>United States</Country>
<MedlineTA>Chem Rec</MedlineTA>
<NlmUniqueID>101085550</NlmUniqueID>
<ISSNLinking>1528-0691</ISSNLinking>
</MedlineJournalInfo>
<KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Möbius rings</Keyword>
<Keyword MajorTopicYN="N">acetylenes</Keyword>
<Keyword MajorTopicYN="N">annulenes</Keyword>
<Keyword MajorTopicYN="N">aromaticity</Keyword>
<Keyword MajorTopicYN="N">carbo-benzenes</Keyword>
</KeywordList>
</MedlineCitation>
<PubmedData><History><PubMedPubDate PubStatus="received"><Year>2014</Year>
<Month>10</Month>
<Day>13</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez"><Year>2015</Year>
<Month>1</Month>
<Day>30</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="pubmed"><Year>2015</Year>
<Month>1</Month>
<Day>30</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline"><Year>2015</Year>
<Month>1</Month>
<Day>30</Day>
<Hour>6</Hour>
<Minute>1</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>ppublish</PublicationStatus>
<ArticleIdList><ArticleId IdType="pubmed">25630606</ArticleId>
<ArticleId IdType="doi">10.1002/tcr.201402091</ArticleId>
</ArticleIdList>
</PubmedData>
</pubmed>
</record>
Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Sante/explor/MersV1/Data/PubMed/Curation
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 001715 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/PubMed/Curation/biblio.hfd -nk 001715 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien |wiki= Sante |area= MersV1 |flux= PubMed |étape= Curation |type= RBID |clé= pubmed:25630606 |texte= Carbo-benzene's aromaticity, before and beyond: a tribute to Nozoe. }}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/PubMed/Curation/RBID.i -Sk "pubmed:25630606" \ | HfdSelect -Kh $EXPLOR_AREA/Data/PubMed/Curation/biblio.hfd \ | NlmPubMed2Wicri -a MersV1
This area was generated with Dilib version V0.6.33. |