Coordination of Sodium Cation to an Oxygen Function and Olefinic Double Bond to Form Molecular Adduct Ion in Fast Atom Bombardment Mass Spectrometry

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Steroidal allylic alcohols formed Na⁺ adduct ion peaks [M+Na]⁺ by the addition of NaCl in FAB mass spectrometry. A comparison of the intensities of the adduct ion peaks of allylic alcohols with those of the corresponding saturated alcohols and olefin suggested that the olefinic double bond and the proximal hydroxyl group had coordinated to Na⁺. The adduct ion was stable and did not undergo dehydroxylation. We suggest that the Na⁺ adduction will be useful for the molecular weight determination of allylic alcohols which are susceptible to dehydroxylation under FAB mass spectrometric conditions. Na⁺ adduct ions of α,β-unsaturated carbonyl compounds were also investigated.