Mass spectrometry of diamantane and some adamantane derivatives

Abstract

The mass spectrometric fragmentation of adamantane, adamantane-d6, diamantane, 1- and 2-adamantanol, and 3,5,7-trimethyl-1-adamantanol has been re-examined, and new data for diamantane and 3,5,7-trimethyl-1-adamantanol are presented in more detail. Metastable peak data have been used to support potential fragmentation pathways. Simple statistical considerations applied to peak intensity data seem to indicate that ionization occurs at the primary bridgehead in both adamantane and diamantane, and that loss of a primary hydrogen is favored over loss of a secondary hydrogen atom.

Diamondoid diacids ('O4' species) in oil sands process‐affected water

“…in addition to the 1,3disubstituted adamantane the 1,2-, 2,4-isomers, two isomers of the 1,4,-2,6-disubstituted adamantane and maybe the dimethyl adamantane-2,2-dicarboxylate (which might not be favoured for steric reasons). [16] While Ib and Ic showed a base peak at m/z 193, indicating a loss of COOCH 3 , the base peak of Id and Ie was at m/z 192, suggesting the loss of the methyl ester molecule via a concerted process involving H-transfer from the charge-retaining fragment, as shown by Waltman and Ling, [17] who described such fragmentations in detail. This has also been reported previously for the EI mass spectrum of the methyl ester of adamantane-2-carboxylic acid.…”

Dissociative ionisation of adamantane: a combined theoretical and experimental study

“…The dissociation of adamantane and diamantane was also studied experimentally in an electron impact mass spectrometer. 19 It was suggested that, analogous to pyrolysis reactions, i.e. dissociation on the neutral surface, the dissociative ionisation of diamondoids yields mostly benzene derivatives.…”

Spectroscopic Characterization of the Product Ions Formed by Electron Ionization of Adamantane

“…IR spectra have been reported for adamantane [26][27][28] and its radical cation, the latter undergoing Jahn-Teller distortion, lowering the symmetry to from T d to C 3v . [32][33][34] Very recently, the gas phase dissociation of adamantane was studied using a combination of Vacuum Ultraviolet (VUV) single photon dissociative ionization measurements and quantum-chemical computations. The dissociation of adamantane (C 10 H 16 ) has been studied in some detail, both experimentally and computationally.…”

“…[31] The fragmentation of adamantane by electron ionization (EI) and proton transfer ionization (PTI) have been studied by mass spectrometry and it was suggested that the cage opens up to form aromatic species. [32][33][34] Very recently, the gas phase dissociation of adamantane was studied using a combination of Vacuum Ultraviolet (VUV) single photon dissociative ionization measurements and quantum-chemical computations. [35] Based on potential energy surface (PES) calculations, structures were suggested for the dissociation products and accurate appearance energies were derived from a statistical model.…”