Regio-isomeric effects in tandem mass spectra of sulfonium cations generated from thiacyclane based sulfonium salts under soft ionization conditions

The influence of regio-isomerism of even-electron sulfonium ions on tandem electrospray and matrix-assisted laser desorption/ionization mass spectra recorded by using collision-induced dissociation was investigated. The initial organic sulfides belonged to isomeric thiabicyclane series (substituted 7- and 8-thiabicyclo[4.3.0]nonanes, 2- and 3-thiabicyclo[4.4.0]decanes) and phenylthiolanes. To investigate by the abovementioned mass spectrometry methods, the sulfides were preliminary S-alkylated by methyl, ethyl iodides, their deuterated analogs and trialkoxonium tetrafluoroborates to form corresponding sulfonium salts. The latter salts readily gave off corresponding sulfonium cations under abovementioned desorption/ionization conditions and these cations were precursor ions in collision-induced dissociation experiments. The main quantitative and frequently qualitative differences between collision-induced dissociation spectra of isomers were manifested in mass numbers and relative intensities of the ions Alk-S+= CHR (formal structure) that originated from the destruction of sulfur-containing ring. Corresponding peaks are particularly abundant for cations Alk-S+= CH2 and their intensities are usually greater than for other C-substituted homologues. Qualitative difference between fragmentation features of 2- and 3-phenylthiolanium cations is that only the latter can eliminate neutral C2H4S molecule. © 2017, © The Author(s) 2017.

Авторы
Zaikin V.G. 1 , Kozlov A.V. 1 , Borisov R.S. 1, 2 , Shchapin I.Y.3
Редакторы
-
Издательство
IM Publications LLP
Номер выпуска
1
Язык
Английский
Страницы
108-115
Статус
Опубликовано
Подразделение
-
Номер
-
Том
24
Год
2018
Организации
  • 1 A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Moscow, Russian Federation
  • 2 People’s Friendship University of Russia, Faculty of physics-mathematics and natural sciences, Moscow, Russian Federation
  • 3 D. I. Mendeleev University of Chemical Technology of Russia, Department of High Energy Chemistry and Radioecology, Moscow, Russian Federation
Ключевые слова
collision-induced dissociation; electrospray; Mass spectrometry; matrix-assisted laser desorption/ionization; regio-isomers; sulfonium salts; thiacyclanes
Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/6876/