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Borinium Adduct Ion Formation with Barbiturates in a Quadrupole Ion‐trap Mass Spectrometer
Author(s) -
Colorado Armando,
Brodbelt Jennifer
Publication year - 1996
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/(sici)1096-9888(199604)31:4<403::aid-jms313>3.0.co;2-0
Subject(s) - chemistry , adduct , mass spectrometry , ion trap , ion , molecule , hydrogen , quadrupole ion trap , organic chemistry , chromatography
Barbiturates are a class of drugs that are utilized as anesthetics and sleeping agents and are used for the treatment of anxiety, epilepsy and other psychiatric disorders. Because of their pyrimidine structures, barbiturates are highly basic compounds. The evaluation of the formation of adducts involving the borinium ion, B(OCH 3 ) 2 + , and the barbiturates in a quadrupole ion trap is described. The adducts [M+73] + dissociate by elimination of methanol followed by the attachment of a trimethylborate or water molecule. This multi‐step pathway is characteristic of a basic, nitrogen‐containing structure that has at least one acidic hydrogen. Model compounds were used to probe the nature of this unusual reaction pathway, which involves nucleophilic attack by a methoxyl oxygen of neutral trimethyl borate at the boron atom of the adduct.