Gaseous anion chemistry. Hydrogen-deuterium exchange in mono- and dialcohol alkoxide ions: ionization reactions in dialcohols

Journal Article · Fri Aug 15 04:00:00 EDT 1980 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo01305a023· OSTI ID:5130196

Lloyd, J R; Agosta, W C; Field, F H

The subject of this work is H-D exchange in certain gaseous anions using D/sub 2/ as the exchanging agent. The anions involved are produced from ethylene glycol, 1,3-propanediol, 1,4-butanediol, ethanol, 1-propanol, and 1-butanol. Spectra and postulated ionization reactions for these mono- and dialcohols are given. Hydrogen-deuterium exchange occurs in the (M - 1)/sup -/ and (2M - 1)/sup -/ ions of ethylene glycol, 1,3-propanediol, and 1,4-butanediol. The amount of exchange occurring is 3-8 times greater in (2M - 1)/sup -/ than in (M - 1)/sup -/. The amount of H-D exchange occurring in ethanol, 1-propanol, and 1-butanol is small or zero in the (2M - 1)/sup -/ ions and in the (M - 1)/sup -/ ion for 1-butanol (the only (M - 1)/sup -/ ion which could be examined experimentally). The amount of exchange occurring in the (2M - 1)/sup -/ and (M - 1)/sup -/ ions from ethylene glycol is not affected by the total pressure or composition of the reaction mixture in the ionization chamber of the mass spectrometer. A novel hydrogen-bridging mechanism is suggested to account for the observed exchange occurring in the dialcohols.

• Research Organization: Rockefeller Univ., New York
• OSTI ID: 5130196
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 45:17; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400303* -- Organic Chemistry-- Isotope Exchange & Isotope Separation-- (-1987)
ALCOHOLS
BUTANOLS
DEUTERIUM
ETHANOL
GLYCOLS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
ISOTOPES
ISOTOPIC EXCHANGE
LIGHT NUCLEI
MASS SPECTROSCOPY
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
PROPANOLS
SPECTROSCOPY
STABLE ISOTOPES