Seleniranium Ions Undergo π-Ligand Exchange via an Associative Mechanism in the Gas Phase.
Identifieur interne : 000B27 ( PubMed/Curation ); précédent : 000B26; suivant : 000B28Seleniranium Ions Undergo π-Ligand Exchange via an Associative Mechanism in the Gas Phase.
Auteurs : S Fern Lim [Australie] ; Benjamin L. Harris [Australie] ; George N. Khairallah [Australie] ; E J Bieske [Australie] ; Philippe Maître [France] ; Gabriel Da Silva [Australie] ; Brian D. Adamson [Australie] ; Michael S. Scholz [Australie] ; Neville J A. Coughlan [Australie] ; Richard A J. O'Hair [Australie] ; Michael Rathjen [Australie] ; Daniel Stares [Australie] ; Jonathan M. White [Australie]Source :
- The Journal of organic chemistry [ 1520-6904 ] ; 2017.
Abstract
Collision-induced dissociation mass spectrometry of the ammonium ions 4a and 4b results in the formation of the seleniranium ion 5, the structure and purity of which were verified using gas-phase infrared spectroscopy coupled to mass spectrometry and gas-phase ion-mobility measurements. Ion-molecule reactions between the ion 5 (m/z = 261) and cyclopentene, cyclohexene, cycloheptene, and cyclooctene resulted in the formation of the seleniranium ions 7 (m/z = 225), 6 (m/z = 239), 8 (m/z = 253), and 9 (m/z = 267), respectively. Further reaction of seleniranium 6 with cyclopentene resulted in further π-ligand exchange giving seleniranium ion 7, confirming that direct π-ligand exchange between seleniranium ion 5 and cycloalkenes occurs in the gas phase. Pseudo-first-order kinetics established relative reaction efficiencies for π-ligand exchange for cyclopentene, cyclohexene, cycloheptene. and cyclooctene as 0.20, 0.07, 0.43, and 4.32. respectively. DFT calculations at the M06/6-31+G(d) level of theory provide the following insights into the mechanism of the π-ligand exchange reactions; the cycloalkene forms a complex with the seleniranium ion 5 with binding energies of 57 and 62 kJ/mol for cyclopentene and cyclohexene, respectively, with transition states for π-ligand exchange having barriers of 17.8 and 19.3 kJ/mol for cyclopentene and cyclohexene, respectively.
DOI: 10.1021/acs.joc.7b00877
PubMed: 28530810
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Harris</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010</wicri:regionArea></affiliation></author><author><name sortKey="Khairallah, George N" sort="Khairallah, George N" uniqKey="Khairallah G" first="George N" last="Khairallah">George N. Khairallah</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010</wicri:regionArea></affiliation></author><author><name sortKey="Bieske, E J" sort="Bieske, E J" uniqKey="Bieske E" first="E J" last="Bieske">E J Bieske</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010</wicri:regionArea></affiliation></author><author><name sortKey="Maitre, Philippe" sort="Maitre, Philippe" uniqKey="Maitre P" first="Philippe" last="Maître">Philippe Maître</name><affiliation wicri:level="1"><nlm:affiliation>Laboratoire de Chimie Physique, Université Paris-Sud, CNRS, Université Paris-Saclay , F-91405 Orsay, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Laboratoire de Chimie Physique, Université Paris-Sud, CNRS, Université Paris-Saclay , F-91405 Orsay</wicri:regionArea></affiliation></author><author><name sortKey="Da Silva, Gabriel" sort="Da Silva, Gabriel" uniqKey="Da Silva G" first="Gabriel" last="Da Silva">Gabriel Da Silva</name><affiliation wicri:level="1"><nlm:affiliation>Chemical and Biomolecular Engineering, University of Melbourne , Parkville, Melbourne 3010, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>Chemical and Biomolecular Engineering, University of Melbourne , Parkville, Melbourne 3010</wicri:regionArea></affiliation></author><author><name sortKey="Adamson, Brian D" sort="Adamson, Brian D" uniqKey="Adamson B" first="Brian D" last="Adamson">Brian D. Adamson</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010</wicri:regionArea></affiliation></author><author><name sortKey="Scholz, Michael S" sort="Scholz, Michael S" uniqKey="Scholz M" first="Michael S" last="Scholz">Michael S. Scholz</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010</wicri:regionArea></affiliation></author><author><name sortKey="Coughlan, Neville J A" sort="Coughlan, Neville J A" uniqKey="Coughlan N" first="Neville J A" last="Coughlan">Neville J A. Coughlan</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010</wicri:regionArea></affiliation></author><author><name sortKey="O Hair, Richard A J" sort="O Hair, Richard A J" uniqKey="O Hair R" first="Richard A J" last="O'Hair">Richard A J. O'Hair</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010</wicri:regionArea></affiliation></author><author><name sortKey="Rathjen, Michael" sort="Rathjen, Michael" uniqKey="Rathjen M" first="Michael" last="Rathjen">Michael Rathjen</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010</wicri:regionArea></affiliation></author><author><name sortKey="Stares, Daniel" sort="Stares, Daniel" uniqKey="Stares D" first="Daniel" last="Stares">Daniel Stares</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010</wicri:regionArea></affiliation></author><author><name sortKey="White, Jonathan M" sort="White, Jonathan M" uniqKey="White J" first="Jonathan M" last="White">Jonathan M. White</name><affiliation wicri:level="1"><nlm:affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010</wicri:regionArea></affiliation></author></analytic><series><title level="j">The Journal of organic chemistry</title><idno type="eISSN">1520-6904</idno><imprint><date when="2017" type="published">2017</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Collision-induced dissociation mass spectrometry of the ammonium ions 4a and 4b results in the formation of the seleniranium ion 5, the structure and purity of which were verified using gas-phase infrared spectroscopy coupled to mass spectrometry and gas-phase ion-mobility measurements. Ion-molecule reactions between the ion 5 (m/z = 261) and cyclopentene, cyclohexene, cycloheptene, and cyclooctene resulted in the formation of the seleniranium ions 7 (m/z = 225), 6 (m/z = 239), 8 (m/z = 253), and 9 (m/z = 267), respectively. Further reaction of seleniranium 6 with cyclopentene resulted in further π-ligand exchange giving seleniranium ion 7, confirming that direct π-ligand exchange between seleniranium ion 5 and cycloalkenes occurs in the gas phase. Pseudo-first-order kinetics established relative reaction efficiencies for π-ligand exchange for cyclopentene, cyclohexene, cycloheptene. and cyclooctene as 0.20, 0.07, 0.43, and 4.32. respectively. DFT calculations at the M06/6-31+G(d) level of theory provide the following insights into the mechanism of the π-ligand exchange reactions; the cycloalkene forms a complex with the seleniranium ion 5 with binding energies of 57 and 62 kJ/mol for cyclopentene and cyclohexene, respectively, with transition states for π-ligand exchange having barriers of 17.8 and 19.3 kJ/mol for cyclopentene and cyclohexene, respectively.</div></front></TEI><pubmed><MedlineCitation Status="In-Data-Review" Owner="NLM"><PMID Version="1">28530810</PMID><DateCreated><Year>2017</Year><Month>05</Month><Day>22</Day></DateCreated><DateRevised><Year>2017</Year><Month>06</Month><Day>16</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-6904</ISSN><JournalIssue CitedMedium="Internet"><Volume>82</Volume><Issue>12</Issue><PubDate><Year>2017</Year><Month>Jun</Month><Day>16</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>Seleniranium Ions Undergo π-Ligand Exchange via an Associative Mechanism in the Gas Phase.</ArticleTitle><Pagination><MedlinePgn>6289-6297</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/acs.joc.7b00877</ELocationID><Abstract><AbstractText>Collision-induced dissociation mass spectrometry of the ammonium ions 4a and 4b results in the formation of the seleniranium ion 5, the structure and purity of which were verified using gas-phase infrared spectroscopy coupled to mass spectrometry and gas-phase ion-mobility measurements. Ion-molecule reactions between the ion 5 (m/z = 261) and cyclopentene, cyclohexene, cycloheptene, and cyclooctene resulted in the formation of the seleniranium ions 7 (m/z = 225), 6 (m/z = 239), 8 (m/z = 253), and 9 (m/z = 267), respectively. Further reaction of seleniranium 6 with cyclopentene resulted in further π-ligand exchange giving seleniranium ion 7, confirming that direct π-ligand exchange between seleniranium ion 5 and cycloalkenes occurs in the gas phase. Pseudo-first-order kinetics established relative reaction efficiencies for π-ligand exchange for cyclopentene, cyclohexene, cycloheptene. and cyclooctene as 0.20, 0.07, 0.43, and 4.32. respectively. DFT calculations at the M06/6-31+G(d) level of theory provide the following insights into the mechanism of the π-ligand exchange reactions; the cycloalkene forms a complex with the seleniranium ion 5 with binding energies of 57 and 62 kJ/mol for cyclopentene and cyclohexene, respectively, with transition states for π-ligand exchange having barriers of 17.8 and 19.3 kJ/mol for cyclopentene and cyclohexene, respectively.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Lim</LastName><ForeName>S Fern</ForeName><Initials>SF</Initials><AffiliationInfo><Affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Harris</LastName><ForeName>Benjamin L</ForeName><Initials>BL</Initials><AffiliationInfo><Affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Khairallah</LastName><ForeName>George N</ForeName><Initials>GN</Initials><AffiliationInfo><Affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Accurate Mass Scientific Pty Ltd., P.O. Box 92, Keilor, VIC 3036, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Bieske</LastName><ForeName>E J</ForeName><Initials>EJ</Initials><Identifier Source="ORCID">http://orcid.org/0000-0003-1848-507X</Identifier><AffiliationInfo><Affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Maître</LastName><ForeName>Philippe</ForeName><Initials>P</Initials><Identifier Source="ORCID">http://orcid.org/0000-0001-6499-5922</Identifier><AffiliationInfo><Affiliation>Laboratoire de Chimie Physique, Université Paris-Sud, CNRS, Université Paris-Saclay , F-91405 Orsay, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>da Silva</LastName><ForeName>Gabriel</ForeName><Initials>G</Initials><Identifier Source="ORCID">http://orcid.org/0000-0003-4284-4474</Identifier><AffiliationInfo><Affiliation>Chemical and Biomolecular Engineering, University of Melbourne , Parkville, Melbourne 3010, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Adamson</LastName><ForeName>Brian D</ForeName><Initials>BD</Initials><AffiliationInfo><Affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Scholz</LastName><ForeName>Michael S</ForeName><Initials>MS</Initials><Identifier Source="ORCID">http://orcid.org/0000-0003-3290-2722</Identifier><AffiliationInfo><Affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Coughlan</LastName><ForeName>Neville J A</ForeName><Initials>NJA</Initials><AffiliationInfo><Affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>O'Hair</LastName><ForeName>Richard A J</ForeName><Initials>RAJ</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-8044-0502</Identifier><AffiliationInfo><Affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Rathjen</LastName><ForeName>Michael</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Stares</LastName><ForeName>Daniel</ForeName><Initials>D</Initials><AffiliationInfo><Affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>White</LastName><ForeName>Jonathan M</ForeName><Initials>JM</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-0707-6257</Identifier><AffiliationInfo><Affiliation>School of Chemistry and Bio21 Institute, University of Melbourne , Parkville, Melbourne 3010, Australia.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2017</Year><Month>06</Month><Day>02</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Org Chem</MedlineTA><NlmUniqueID>2985193R</NlmUniqueID><ISSNLinking>0022-3263</ISSNLinking></MedlineJournalInfo></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2017</Year><Month>5</Month><Day>23</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2017</Year><Month>5</Month><Day>23</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2017</Year><Month>5</Month><Day>23</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">28530810</ArticleId><ArticleId IdType="doi">10.1021/acs.joc.7b00877</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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