Collision-induced dissociations of carboxylate negative ions from 2-ethylbutanoic, 2-methylpropanoic, and pivalic acids. An isotopic labelling study

Abstract
Deprotonation of Et2CHCO2H yields Et2CHCO2 . On collisional activation this ion forms CO2 ˙, CH2 CH, and MeCHCH. In addition, elimination of H˙ and Et˙ yield Et(R)CCO2 ˙(R = Et and H, respectively). The elimination of Et˙ is not a simple cleavage but occurs by loss of H˙ from a methyl group followed by loss of ethene. The carboxylate ion also rearranges to Et2CCO2H; this species decomposes to HO, EtCCH2, and also eliminates the elements of C3H8 and CH4. All fragmentations have been studied using 2H and 13C labelling: for example it is proposed that loss of CH4 from Et2CCO2H occurs by a six-centre stepwise process in which the first step (formation of an incipient methyl anion) is rate determining. The collisional activation mass spectra of Et2CHCO2 , Me2CHCO2 , and Me3CCO2 are different, all showing characteristic decompositions. For example, all three ions eliminate methane; the mechanism is different in each case.