Ortho effect in the mass spectrometric behaviour of N-(pyrimidin-4-yl)aminobenzoic acids and their methyl esters

Ortho-, mesa- and para-isomers of N-(pyrimidin-4yl)aminobenzoic acid and their methyl esters were investigated by electron impact mass spectrometry. Their fragmentation was found to be strongly dependent on the position of the substituent in the aminobenzoic moiety. Two different kinds of ortho effect were studied and confirmed with the aid of deuterium-labelled derivatives

[1]  J. Spychała,et al.  Mass spectrometry of N-(pyrimidin-2-yl)amino acids and their methyl esters , 1991 .

[2]  L. Celewicz,et al.  Mass spectrometry of pyrimidine derivatives: Electron impact‐induced decomposition of molecular ions of 4‐amino‐substituted and 4‐amino‐disubstituted 1,2‐dihydro‐1‐methylpyrimidin‐2‐ones , 1991 .

[3]  K. Golankiewicz,et al.  The Efficient Method of Synthesis of 4-N-Arylcytosines , 1990 .

[4]  L. Celewicz,et al.  Mass spectrometry of some methyl esters of N-4-pyrimidinylamino acids: Rearrangements of the ions occurring on electron-impact ionization , 1990 .

[5]  A. S. Plaziak,et al.  Stabilization of even-electron ions in 4-amino-substituted cytosines. Appearance of the strong ortho effect between an aryl substituent and the pyrimidinyl ring , 1989 .

[6]  J. Starrett,et al.  Preparation of 1-(2,3-dideoxy-.beta.-D-glycero-pent-2-enofuranosyl)thymine (d4T) and 2',3'-dideoxyadenosine (ddA): general methods for the synthesis of 2',3'-olefinic and 2',3'-dideoxy nucleoside analogs active against HIV , 1989 .

[7]  A. Matsuda,et al.  A NEW METHOD FOR SYNTHESIZING THE ANTINEOPLASTIC NUCLEOSIDES 1-(2-AZIDO-2-DEOXY-β-D-ARABINOFURANOSYL)CYTOSINE (CYTARAZID) AND 1-(2-AMINO-2-DEOXY-β-D-ARABINOFURANOSYL)CYTOSINE (CYTARAMIN) FROM URIDINE , 1989 .

[8]  L. Celewicz,et al.  Mass spectrometry of 4N-pyrimidinyl amino acids , 1989 .

[9]  L. Celewicz,et al.  Stabilization of even-electron ions by cyclization of substituents on 3N- and 4N-nitrogens in 4N-substituted cytosines , 1988 .

[10]  E. Clercq.  Chemotherapeutic approaches to the treatment of the acquired immune deficiency syndrome (AIDS). , 1986 .

[11]  Roland K. Robins,et al.  Synthetic Antiviral Agents , 1986 .

[12]  H. Schwarz.  Some newer aspects of mass spectrometric ortho effects , 1978 .

[13]  R. H. Hall.  The modified nucleosides in nucleic acids , 1971 .