The High-Resolution Mass Spectrum of Barbital

HISAO NAKATA; AKIRA TATEMATSU; HITOSHI TSUYAMA; HIROSHI DOI

doi:10.5702/massspec1953.15.112

HISAO NAKATA, AKIRA TATEMATSU, HITOSHI TSUYAMA, HIROSHI DOI

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1967 Volume 15 Issue 2 Pages 112-121

DOI https://doi.org/10.5702/massspec1953.15.112

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Published: June 25, 1967 Received: December 19, 1966 Available on J-STAGE: June 28, 2010 Accepted: - Advance online publication: - Revised: -
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Date of correction: June 28, 2010 Reason for correction: - Correction: DTRECEIVED Details: Right : 19661219

Date of correction: June 28, 2010 Reason for correction: - Correction: ABSTRACT Details: Wrong : The mass spectral fragmentation patterns of barbital(diethylbarbituric acid)were studied by using the high-resolution mass spectrometry. As is shown in Fig. 1, barbital exhibits several characteristic peaks correlated each other by the existence of meta-stable ion peaks(Fig. 2). The accurate masses of apeak at m/e156were determined by the peak-matching technique with an M+2peak of diphenyl as a standard(TableI). Peaks at m/e155, 141, 112, and83were examined in the similar manner with suitably chosen standard substances, and the results were summarized in Table II. Elemental compositions of the main fragment ions of peaks at m/e98, 70, 69, 55, 44, and41 were assigned from comparison of allowed atomic combinations with the number of observed peaks(Fig. 3∼8, Table III∼VIII). Fragment ions and fragmentation sequences of barbital were represented in Fig. 9. Plausible mechanistic formulations of each fragmentation step were depicted in Eq. 1, 2, 3, 4, and5, respectively. It was noted that the interconversion of keto-and enol-forms of M-28ion(m/e156)(Eq. 6)was not possible in a mass spectrometer.
Right : The mass spectral fragmentation patterns of barbital (diethylbarbituric acid) were studied by using the high-resolution mass spectrometry. As is shown in Fig. 1, barbital exhibits several characteristic peaks correlated each other by the existence of meta-stable ion peaks (Fig. 2) .
The accurate masses of apeak at m/e156 were determined by the peak-matching technique with an M+2 peak of diphenyl as a standard (TableI) . Peaks at m/e 155, 141, 112, and 83 were examined in the similar manner with suitably chosen standard substances, and the results were summarized in Table II.
Elemental compositions of the main fragment ions of peaks at m/e 98, 70, 69, 55, 44, and 41 were assigned from comparison of allowed atomic combinations with the number of observed peaks (Fig. 3-8, Table III-VIII). Fragment ions and fragmentation sequences of barbital were represented in Fig. 9.
Plausible mechanistic formulations of each fragmentation step were depicted in Eq. 1, 2, 3, 4, and 5, respectively. It was noted that the interconversion of keto-and enol-forms of M-28 ion(m/e156)(Eq. 6)was not possible in a mass spectrometer.

Date of correction: June 28, 2010 Reason for correction: - Correction: CITATION Details: Right : J. H. Beynon, A. E. Williams,“Mass and Abundance Tables for Use in Mass Spectrometry”, Elsevier, Amsterdam(1963).
A. Costopanagiotis, H. Budzikiewicz, Monatsh., 96, 1800(1965).
H-F. Grutzmacher, W. Arnold, Tetrahedron Letters, 1966, 1365.
T. Goto, A. Tatematsu, Y. Nakajima, H Tsuyama, Tetrahedron Letters, 5, 1965, 757.
T. Goto, A. Tatematsu, S. Matsuura, J. Org Chem., 30, 1844(1965).
F. W. McLafferty, Anal. Chem., 31, 477(1959).
M. M. Bursey, F. W. McLafferty, J. Am. Chem. Soc., 88, 529, 4484(1966)ibid, 89, 1(1967).

Abstract

The mass spectral fragmentation patterns of barbital (diethylbarbituric acid) were studied by using the high-resolution mass spectrometry. As is shown in Fig. 1, barbital exhibits several characteristic peaks correlated each other by the existence of meta-stable ion peaks (Fig. 2) .
The accurate masses of apeak at m/e156 were determined by the peak-matching technique with an M+2 peak of diphenyl as a standard (TableI) . Peaks at m/e 155, 141, 112, and 83 were examined in the similar manner with suitably chosen standard substances, and the results were summarized in Table II.
Elemental compositions of the main fragment ions of peaks at m/e 98, 70, 69, 55, 44, and 41 were assigned from comparison of allowed atomic combinations with the number of observed peaks (Fig. 3-8, Table III-VIII). Fragment ions and fragmentation sequences of barbital were represented in Fig. 9.
Plausible mechanistic formulations of each fragmentation step were depicted in Eq. 1, 2, 3, 4, and 5, respectively. It was noted that the interconversion of keto-and enol-forms of M-28 ion(m/e156)(Eq. 6)was not possible in a mass spectrometer.

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