TY - JOUR
T1 - The mass spectrometry-induced cyclization of protonated N-[2-(benzoyloxy)phenyl]-benzamide
T2 - A gas-phase analog of a solution reaction
AU - Moolayil, Joseph T.
AU - George, M.
AU - Srinivas, R.
AU - Swamy, N. S.
AU - Russell, Amber L.
AU - Giblin, Daryl E.
AU - Gross, Michael L.
N1 - Funding Information:
The authors J.T.M. and M.G. thank the Kerala State Council for Science Technology and Environment for financial assistance and Principal, S.H. College, Thevara for providing infrastructure. R.S. and N.S.S. thank Dr J.S. Yadav, Director, IICT, Hyderabad, for facilities and Dr M. Vairamani for cooperation. Research at Washington University was supported by the National Centers for Research Resources of the NIH, Grant P41RR00954.
PY - 2006/3/1
Y1 - 2006/3/1
N2 - A cyclization of N-[2-(benzoyloxy)phenyl]-benzamide, accompanied by the elimination of a molecule of benzoic acid, takes place in a mass spectrometer upon protonation by fast atom bombardment (FAB) or electrospray ionization (ESI). The elimination of benzoic acid from the [M + H]+ yields protonated 2-phenylbenzoxazole by a process that is analogous to the acid catalyzed cyclization of N-[2-(benzoyloxy)phenyl]-benzamide in solution. A similar elimination of benzoic acid occurs from the molecular radical cation produced by electron ionization (EI). The proposed cyclization and elimination of benzoic acid are supported by accurate mass measurements, product-ion spectra in tandem mass spectrometry (MS/MS), mass spectra of reference compounds, isotopic labeling, and molecular modeling by density functional theory.
AB - A cyclization of N-[2-(benzoyloxy)phenyl]-benzamide, accompanied by the elimination of a molecule of benzoic acid, takes place in a mass spectrometer upon protonation by fast atom bombardment (FAB) or electrospray ionization (ESI). The elimination of benzoic acid from the [M + H]+ yields protonated 2-phenylbenzoxazole by a process that is analogous to the acid catalyzed cyclization of N-[2-(benzoyloxy)phenyl]-benzamide in solution. A similar elimination of benzoic acid occurs from the molecular radical cation produced by electron ionization (EI). The proposed cyclization and elimination of benzoic acid are supported by accurate mass measurements, product-ion spectra in tandem mass spectrometry (MS/MS), mass spectra of reference compounds, isotopic labeling, and molecular modeling by density functional theory.
KW - Cyclization
KW - Density functional theory
KW - Electrospray ionization
KW - Fast atom bombardment
KW - Solution analogy
UR - http://www.scopus.com/inward/record.url?scp=33344462982&partnerID=8YFLogxK
U2 - 10.1016/j.ijms.2006.01.014
DO - 10.1016/j.ijms.2006.01.014
M3 - Article
AN - SCOPUS:33344462982
SN - 1387-3806
VL - 249-250
SP - 21
EP - 30
JO - International Journal of Mass Spectrometry
JF - International Journal of Mass Spectrometry
ER -