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Evidence for the cyclic CN carbene in the gas phase

Organic Letters, ISSN: 1523-7052, Vol: 16, Issue: 20, Page: 5482-5485
2014
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Article Description

3-Halodiazirine-3-carboxylic acids (c-CN XCOOH, X = Cl or Br) were prepared from their esters and converted to the corresponding sodium salts. Collision-induced dissociation (CID) of the carboxylate ions led exclusively to the loss of CO and the resulting c-CN X ions dissociated to c-CN carbene at low energies. The bond dissociation energy (BDE) for c-CN Br was found to be less than 8 kcal/mol using CID of the anion generated by electrospray ionization of the carboxylate. The analogous difluoro system (CF XCOOH/CF X /CF ) exhibits similar dissociative behavior. All experimental BDEs are in very good agreement with MP4/aug-cc-pVTZ calculations. (Chemical Equation Presented).

Bibliographic Details

Hanzlová, Eva; Váňa, Jiří; Shaffer, Christopher J; Roithová, Jana; Martinů, Tomáš

American Chemical Society (ACS)

Biochemistry, Genetics and Molecular Biology; Chemistry

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