Reduction of nitriles to amines in positive ion electrospray ionization mass spectrometry.
Some compounds readily form [M+46]+ adduct ions during positive ion electrospray ionization mass spectrometry ((+)ESI-MS) analysis. These [M+46]+ ions were characterized as [M+CH3CH2NH2+H]+ by accurate mass determination. Ethylamine involved in the adduct was proposed to be the reduction product of acetonitrile and this was confirmed using deuterated acetonitrile. Other nitrile-containing compounds tested, including isobutyronitrile and benzonitrile, also formed the adduct ions of the respective amine forms under (+)ESI-MS conditions. Hydrogen/deuterium exchange experiments demonstrated that the reductive hydrogen originated from water. Reduction of nitriles (R-CN) to their respective amines (R-CH2NH2) under (+)ESI-MS conditions expands the ability to identify nitrile-containing chemical unknowns.
Gu
Zhe-Ming
ZM
XenoBiotic Laboratories, Inc., Plainsboro, NJ 08536, USA. zheming@xbl.com
Ma
Jiyuan
J
Zhao
Xian-Guo
XG
Wu
Jinn
J
Zhang
Donglu
D
D000097:Acetonitriles / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D003903:Deuterium / Q000737:chemistry; D005021:Ethylamines / Q000737:chemistry; D007553:Isotope Labeling; D009570:Nitriles / Q000737:chemistry*; D010084:Oxidation-Reduction; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*
D000097:Acetonitriles; D000588:Amines; D005021:Ethylamines; D009570:Nitriles; C022246:isobutyronitrile; C014356:benzonitrile; D003903:Deuterium; C041564:ethylamine; C032159:acetonitrile