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https://hdl.handle.net/2440/4714
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Type: | Journal article |
Title: | Search for charge-remote reactions of even-electron organic negative ions in the gas phase. Anions derived from disubstituted adamantanes |
Author: | Dua, S. Bowie, J. Cerda, B. Wesdemiotis, C. |
Citation: | Journal of the Chemical Society, Perkin Transactions 2, 1998; 2(6):1443-1448 |
Publisher: | ROYAL SOC CHEMISTRY |
Issue Date: | 1998 |
ISSN: | 1472-779X 1364-5471 |
Statement of Responsibility: | Dua, Suresh; Bowie, John H.; Cerda, Blas A.; Wesdemiotis, Chrys |
Abstract: | The collision induced decompositions of 3-substituted adamantanecarboxylate anions have been studied with a view to uncover charge-remote fragmentations of the 3-substituent. The 3-substituent is chosen so that it cannot approach the anion site and therefore any fragmentations of that substituent should proceed independently of the charged centre, (i) Charge-remote radical losses are observed from a 3-CH(Et)2 substituent [e.g. Eṫ and ̇CH(Et)2 losses], but the classical Adams-Gross charge remote loss of an ethene plus dihydrogen is not observed, (ii) Charge-remote loss of MeOD is observed from a 3-C(CD3)2(OMe) substituent together with a number of charge-remote radical losses [e.g. Mė, MeȮ and ̇C(CD3)2(OMe)]. (iii) The 3-substituent C(CD3)2 (OCH=O) undergoes charge-remote loss of HCO2D for both the carboxylate anion and its corresponding cation, a neutral reaction analogous to both the McLafferty rearrangement of radical cations and the Norrish II diradical rearrangement of aliphatic ketones. (iv) The charge-remote radical losses of MeȮ and ̇CO2Me occur from a 3-CO2Me substituent. |
DOI: | 10.1039/a708654g |
Published version: | http://dx.doi.org/10.1039/a708654g |
Appears in Collections: | Aurora harvest 2 Chemistry publications |
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