Deprotonation of Lithiated Benzenes.
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| Title: | Deprotonation of Lithiated Benzenes. |
|---|---|
| Authors: | Bachrach, Steven M.1 sbachrach@trinity.edu, Chamberlin, Adam C.1 |
| Source: | Journal of Organic Chemistry. 3/19/2004, Vol. 69 Issue 6, p2111-2122. 12p. 8 Diagrams, 7 Charts. |
| Subjects: | Organolithium compounds, Benzene, Aromatic compounds, Organometallic compounds, Protons, Organic chemistry |
| Abstract: | The deprotonation energies of all possible lithiobenzenes (C6LinH6-n, n = 0-5) were computed at B3LYP/6-311+G(d,p). Based on natural population analysis, the conjugate bases can be thought of as salts between a polyanionic phenyl core and associated lithium cations. The most stable structures maximize the electrostatic attraction between these two species, typically by positioning the lithium cations to bridge in the ring plane across two adjacent carbanion centers. Favorable deprotonation occurs when the formal carbanion centers are adjacent to each other and then the proton is removed from an adjacent carbon. The deprotonation free energies range from 365.0 to 397.2 kcal mol-1, with most of them less than the deprotonation free energy of benzene (391.8 kcal mol-1). [ABSTRACT FROM AUTHOR] |
| Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| Database: | Engineering Source |
| FullText | Text: Availability: 0 |
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| Header | DbId: egs DbLabel: Engineering Source An: 12879525 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Deprotonation of Lithiated Benzenes. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Bachrach%2C+Steven+M%2E%22">Bachrach, Steven M.</searchLink><relatesTo>1</relatesTo><i> sbachrach@trinity.edu</i><br /><searchLink fieldCode="AR" term="%22Chamberlin%2C+Adam+C%2E%22">Chamberlin, Adam C.</searchLink><relatesTo>1</relatesTo> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 3/19/2004, Vol. 69 Issue 6, p2111-2122. 12p. 8 Diagrams, 7 Charts. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Organolithium+compounds%22">Organolithium compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Benzene%22">Benzene</searchLink><br /><searchLink fieldCode="DE" term="%22Aromatic+compounds%22">Aromatic compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Organometallic+compounds%22">Organometallic compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Protons%22">Protons</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+chemistry%22">Organic chemistry</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: The deprotonation energies of all possible lithiobenzenes (C6LinH6-n, n = 0-5) were computed at B3LYP/6-311+G(d,p). Based on natural population analysis, the conjugate bases can be thought of as salts between a polyanionic phenyl core and associated lithium cations. The most stable structures maximize the electrostatic attraction between these two species, typically by positioning the lithium cations to bridge in the ring plane across two adjacent carbanion centers. Favorable deprotonation occurs when the formal carbanion centers are adjacent to each other and then the proton is removed from an adjacent carbon. The deprotonation free energies range from 365.0 to 397.2 kcal mol-1, with most of them less than the deprotonation free energy of benzene (391.8 kcal mol-1). [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1021/jo035265l Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 12 StartPage: 2111 Subjects: – SubjectFull: Organolithium compounds Type: general – SubjectFull: Benzene Type: general – SubjectFull: Aromatic compounds Type: general – SubjectFull: Organometallic compounds Type: general – SubjectFull: Protons Type: general – SubjectFull: Organic chemistry Type: general Titles: – TitleFull: Deprotonation of Lithiated Benzenes. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Bachrach, Steven M. – PersonEntity: Name: NameFull: Chamberlin, Adam C. IsPartOfRelationships: – BibEntity: Dates: – D: 19 M: 03 Text: 3/19/2004 Type: published Y: 2004 Identifiers: – Type: issn-print Value: 00223263 Numbering: – Type: volume Value: 69 – Type: issue Value: 6 Titles: – TitleFull: Journal of Organic Chemistry Type: main |
| ResultId | 1 |
