Seleniranium Ions Undergo π-Ligand Exchange via an Associative Mechanism in the Gas Phase.
Identifieur interne : 000388 ( Main/Exploration ); précédent : 000387; suivant : 000389Seleniranium 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
Affiliations:
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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><placeName><settlement type="city">Melbourne</settlement><region type="état">Victoria (État)</region></placeName></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><placeName><settlement type="city">Melbourne</settlement><region type="état">Victoria (État)</region></placeName></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><placeName><settlement type="city">Melbourne</settlement><region type="état">Victoria (État)</region></placeName></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><placeName><settlement type="city">Melbourne</settlement><region type="état">Victoria (État)</region></placeName></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><placeName><settlement type="city">Melbourne</settlement><region type="état">Victoria (État)</region></placeName></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><placeName><settlement type="city">Melbourne</settlement><region type="état">Victoria (État)</region></placeName></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><placeName><settlement type="city">Melbourne</settlement><region type="état">Victoria (État)</region></placeName></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><affiliations><list><country><li>Australie</li><li>France</li></country><region><li>Victoria (État)</li><li>Île-de-France</li></region><settlement><li>Melbourne</li><li>Orsay</li></settlement><orgName><li>Université Paris-Sud</li></orgName></list><tree><country name="Australie"><region name="Victoria (État)"><name sortKey="Lim, S Fern" sort="Lim, S Fern" uniqKey="Lim S" first="S Fern" last="Lim">S Fern Lim</name></region><name sortKey="Adamson, Brian D" sort="Adamson, Brian D" uniqKey="Adamson B" first="Brian D" last="Adamson">Brian D. Adamson</name><name sortKey="Bieske, E J" sort="Bieske, E J" uniqKey="Bieske E" first="E J" last="Bieske">E J Bieske</name><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><name sortKey="Da Silva, Gabriel" sort="Da Silva, Gabriel" uniqKey="Da Silva G" first="Gabriel" last="Da Silva">Gabriel Da Silva</name><name sortKey="Harris, Benjamin L" sort="Harris, Benjamin L" uniqKey="Harris B" first="Benjamin L" last="Harris">Benjamin L. Harris</name><name sortKey="Khairallah, George N" sort="Khairallah, George N" uniqKey="Khairallah G" first="George N" last="Khairallah">George N. Khairallah</name><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><name sortKey="Rathjen, Michael" sort="Rathjen, Michael" uniqKey="Rathjen M" first="Michael" last="Rathjen">Michael Rathjen</name><name sortKey="Scholz, Michael S" sort="Scholz, Michael S" uniqKey="Scholz M" first="Michael S" last="Scholz">Michael S. Scholz</name><name sortKey="Stares, Daniel" sort="Stares, Daniel" uniqKey="Stares D" first="Daniel" last="Stares">Daniel Stares</name><name sortKey="White, Jonathan M" sort="White, Jonathan M" uniqKey="White J" first="Jonathan M" last="White">Jonathan M. White</name></country><country name="France"><region name="Île-de-France"><name sortKey="Maitre, Philippe" sort="Maitre, Philippe" uniqKey="Maitre P" first="Philippe" last="Maître">Philippe Maître</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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