Seeking the most stable isomer of azahomocubanes
This study examines the stability and protonation properties of four potential azahomocubanes. Through high-level ab initio computations, we find that 9-azahomocubane is the most stable isomer, closely followed by 5-azahomocubane, 1-azahomocubane, and 2-azahomocubane. However, understanding the stab...
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| Veröffentlicht in: | RSC advances 2023-09, Vol.13 (4), p.27672-27675 |
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| creator | Fernández-Herrera, María A Barroso-Flores, Joaquín Merino, Gabriel |
| description | This study examines the stability and protonation properties of four potential azahomocubanes. Through high-level
ab initio
computations, we find that 9-azahomocubane is the most stable isomer, closely followed by 5-azahomocubane, 1-azahomocubane, and 2-azahomocubane. However, understanding the stability of the systems with a nitrogen atom incorporated into a highly constrained polycyclic environment extends beyond mere bond angles or hybridization considerations. Strain energy analysis reveals that azahomocubanes experience less strain compared to their carbon congeners. An exploration of multiple solvents shows that their impact on relative energies and geometries is negligible. On the other hand, among the four isomers, 2-azahomocubane exhibits the highest tendency for protonation. Basicity, as assessed through the minimum electrostatic potential, correlates well with protonation affinities.
The stability and protonation properties of four potential azahomocubanes are examined. |
| doi_str_mv | 10.1039/d3ra05117j |
| format | Article |
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ab initio
computations, we find that 9-azahomocubane is the most stable isomer, closely followed by 5-azahomocubane, 1-azahomocubane, and 2-azahomocubane. However, understanding the stability of the systems with a nitrogen atom incorporated into a highly constrained polycyclic environment extends beyond mere bond angles or hybridization considerations. Strain energy analysis reveals that azahomocubanes experience less strain compared to their carbon congeners. An exploration of multiple solvents shows that their impact on relative energies and geometries is negligible. On the other hand, among the four isomers, 2-azahomocubane exhibits the highest tendency for protonation. Basicity, as assessed through the minimum electrostatic potential, correlates well with protonation affinities.
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ab initio
computations, we find that 9-azahomocubane is the most stable isomer, closely followed by 5-azahomocubane, 1-azahomocubane, and 2-azahomocubane. However, understanding the stability of the systems with a nitrogen atom incorporated into a highly constrained polycyclic environment extends beyond mere bond angles or hybridization considerations. Strain energy analysis reveals that azahomocubanes experience less strain compared to their carbon congeners. An exploration of multiple solvents shows that their impact on relative energies and geometries is negligible. On the other hand, among the four isomers, 2-azahomocubane exhibits the highest tendency for protonation. Basicity, as assessed through the minimum electrostatic potential, correlates well with protonation affinities.
The stability and protonation properties of four potential azahomocubanes are examined.</description><subject>Angles (geometry)</subject><subject>Basicity</subject><subject>Chemistry</subject><subject>Congeners</subject><subject>Isomers</subject><subject>Protonation</subject><subject>Stability</subject><subject>Strain analysis</subject><subject>Strain energy</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdkdtLwzAYxYsoOOZefBcKvohQ_ZI0afskY94ZCF6eQ5ImW2fbzKQV9K83c2Ne8pLDl18O3-FE0SGCMwSkOC-JE0ARyhY70QBDyhIMrNj9pfejkfcLCIdRhBkaRPCk9WvVzuJuruPG-i72nZC1jitvG-1ia2LxKea2saqXotX-INozovZ6tLmH0cv11fPkNpk-3NxNxtNEpcC6RMrUkFIVuSmhYFpRotMCqVJpU9IMS8NyHWYIixTKHFOQQUsFGGOJDMrIMLpY-y572ejwr-2cqPnSVY1wH9yKiv99aas5n9l3joCGdIQFh5ONg7NvvfYdbyqvdF2HGLb3HOeMZbQAggN6_A9d2N61IV-gMkRJSrIVdbqmlLPeO2222yDgqwb4JXkcfzdwH-CjNey82nI_DZEvMRqCaQ</recordid><startdate>20230918</startdate><enddate>20230918</enddate><creator>Fernández-Herrera, María A</creator><creator>Barroso-Flores, Joaquín</creator><creator>Merino, Gabriel</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-0554-7569</orcidid><orcidid>https://orcid.org/0000-0003-2527-9848</orcidid><orcidid>https://orcid.org/0000-0003-1961-8321</orcidid></search><sort><creationdate>20230918</creationdate><title>Seeking the most stable isomer of azahomocubanes</title><author>Fernández-Herrera, María A ; Barroso-Flores, Joaquín ; Merino, Gabriel</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c406t-bb4f3dc98fd096ec53e491cdcefd572bf68e53e12a40d8250be12bc0222b1f173</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Angles (geometry)</topic><topic>Basicity</topic><topic>Chemistry</topic><topic>Congeners</topic><topic>Isomers</topic><topic>Protonation</topic><topic>Stability</topic><topic>Strain analysis</topic><topic>Strain energy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fernández-Herrera, María A</creatorcontrib><creatorcontrib>Barroso-Flores, Joaquín</creatorcontrib><creatorcontrib>Merino, Gabriel</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fernández-Herrera, María A</au><au>Barroso-Flores, Joaquín</au><au>Merino, Gabriel</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Seeking the most stable isomer of azahomocubanes</atitle><jtitle>RSC advances</jtitle><date>2023-09-18</date><risdate>2023</risdate><volume>13</volume><issue>4</issue><spage>27672</spage><epage>27675</epage><pages>27672-27675</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>This study examines the stability and protonation properties of four potential azahomocubanes. Through high-level
ab initio
computations, we find that 9-azahomocubane is the most stable isomer, closely followed by 5-azahomocubane, 1-azahomocubane, and 2-azahomocubane. However, understanding the stability of the systems with a nitrogen atom incorporated into a highly constrained polycyclic environment extends beyond mere bond angles or hybridization considerations. Strain energy analysis reveals that azahomocubanes experience less strain compared to their carbon congeners. An exploration of multiple solvents shows that their impact on relative energies and geometries is negligible. On the other hand, among the four isomers, 2-azahomocubane exhibits the highest tendency for protonation. Basicity, as assessed through the minimum electrostatic potential, correlates well with protonation affinities.
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; PubMed Central Open Access |
| subjects | Angles (geometry) Basicity Chemistry Congeners Isomers Protonation Stability Strain analysis Strain energy |
| title | Seeking the most stable isomer of azahomocubanes |
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