Mass spectra interpretation of some thiophosphororganic compounds

Moldovan, Zaharie; Nicoarã, Simona; Culea, Monica; Cozar, O.; Fenesan, I.; Végh, Péter; Ríos, José Julián

doi:10.1016/0022-2860(95)08671-h

Cited by 3 publications

(7 citation statements)

References 6 publications

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“…Organophosphorus compounds exhibit biological activity in a large variety of ways,1–3 and have been widely studied by physical and physicochemical methods, especially by mass spectrometry 1–10. Substances 1–5 were synthesized11 and found to be biologically active 4.…”

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confidence: 99%

Electron impact mass spectral interpretation for some thiophosphoryl‐p‐acetylaminobenzenesulfonamides

Fenesan¹,

Popescu²,

Supuran³

et al. 2001

Rapid Comm Mass Spectrometry

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This work discusses the synthesis and the fragmentation patterns for 2-(p-acetylaminosulfonamido)-2-thiono-(5,5-dimethyl-1,3,2-dioxaphosphorinane)(1) and for the p-acetylaminosulfonylamides of O,O-diethylthiophosphoric acid (2), O,O-diphenylthiophosphoric acid (3), dimethylaminocyclohexylthiophosphoric acid (4), and diethylaminophenylthiophosphoric acid (5). A thionamidic-thiolimidic structure was attributed to compounds 1-5, consistent with their IR and NMR spectra. EI mass spectra at 70 eV, high resolution (HR) mass measurements and metastable ion spectra were used to elucidate the fragmentation processes and to determine the kinetic energy release values associated with the metastable ion dissociations. HR accurate mass measurements were used to confirm the compositions of the more abundant ions.

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mentioning

confidence: 99%

Electron impact mass spectral interpretation for some thiophosphoryl‐p‐acetylaminobenzenesulfonamides

Fenesan¹,

Popescu²,

Supuran³

et al. 2001

Rapid Comm Mass Spectrometry

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“…In the range of low masses, all the four spectra exhibit characteristic peaks at m/z 76, 51 and 50, typical aryl fragments 11,. 12b…”

Section: Resultsmentioning

confidence: 95%

“…This generates the ion o, m/z (104 + R), that produces detectable peaks (>10%) in all the spectra except that of compound 4 , for which fewer peaks were recorded in general. Simultaneous elimination of multiple neutrals has been encountered in other thioorganophosphorus molecules containing a phenyl group 11,. 12…”

Section: Resultsmentioning

confidence: 99%

“…Thiophosphororganic derivatives are well known as having a remarkable biological potential,1–4 and some new compounds have been proven to possess antimicrobial and therapeutic properties 5–8. Among other methods, the mass spectrometry technique is a useful tool in their structural characterisation, identification and quantitative determination 9–17…”

Section: Structures and Molecular Masses Of The Compounds Studiedmentioning

confidence: 99%

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Electron ionisation mass spectral analysis and fragmentation pathways for some thiophosphorylicp‐carboxybenzene sulfonamides

Nicoarã

Culea

2002

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The work presents the 70 eV electron impact mass spectra of some thiophosphorylic p-carboxybenzene sulfonamides, and proposes rationalisation of their fragmentation pathways. Accurate mass measurements of the fragment ions, and metastable ion analyses performed in the MIKES mode, were used to elucidate the most abundant ion compositions and to elucidate the fragmentation patterns of these pharmacologically interesting compounds.

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“…[4][5][6][7] The aim of this work is to study the electron impact mass spectra and to propose a fragmentation pattern for the new p-arylsulfonamides synthesized at the Chemistry Institute "Raluca Ripan". The compounds are expected to have biological activity, due to their structure and elemental composition:…”

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confidence: 99%

Mass spectral study of the fragmentation pathways for some new thiophosphororganic molecules

Culea

Palibroda

Moldovan

et al. 1998

Rapid Commun. Mass Spectrom.

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The electron impact ionization mass spectra of the p-carboxyphenylsulfonylamide (1), p-carbomethoxyphenylsulfonylamide (2), p-methoxyphenylsulfonylamide (3) and p-fluorophenylsulfonylamide (4), of O,Odiphenyl-thiophosphoric acid, are discussed and interpreted, based on accurate mass measurements and metastable ion analysis. The fragmentation pattern shows common features for all compounds. Some cleavage processes specific to the radicals bonded to the aryl site are observed in each spectrum. # 1998 John Wiley & Sons, Ltd. Received 20 June 1998; Revised 7 September 1998; Accepted 9 September 1998 Due to their biological activity, organic thiophosophonic compounds have been extensively studied lately.1-3 Mass spectrometry is an important tool in the molecular structure analysis of these substances. [4][5][6][7] The aim of this work is to study the electron impact mass spectra and to propose a fragmentation pattern for the new p-arylsulfonamides synthesized at the Chemistry Institute "Raluca Ripan". The compounds are expected to have biological activity, due to their structure and elemental composition: RESULTS AND DISCUSSIONFigures 1-4. present the 70 eV EI mass spectra of compounds 1-4, and in Table 1 are listed the mass-tocharge ratios and their relative abundances for the main fragment ions from the fragmentation pattern exhibited in Scheme 1. The molecular ion M Á , m/z (404 Y), has low abundance (3) or is even missing altogether (1 and 2), due to a higher degree of fragmentation. A fairly abundant (18 %) molecular ion is observed in the mass spectrum of 4, with a fluorine atom bonded to the aryl group. The ion a, m/z (294 Y), probably results from the cleavage of the thiolic isomer [M']Á of the molecular ion (Scheme 1), by the elimination of a neutral C 6 H 5 SH molecule. Similar eliminations, subsequent to a thionethiol isomerization, were observed in other O,O-diphenylthiophosphonic derivatives analysed in the same laboratory. 8 Metastable ion detection in the mass analysed kinetic energy (MIKES) mode confirmed that ion a further decomposes into ion b, m/z (76 Y), and ion e, m/z (139 Y), respectively, by losing the neutral group C 6 H 4 O 3 P. The kinetic energy released was estimated in the MIKE scanning mode, 9,10 from the width at half height of the Gaussian shaped peaks. The a → b transition appears to be different from a simple bond fission. It probably takes place by the cleavage of the S-C bond, involving electrons withdrawn by the SO 2 group with the positive charge left on the aryl group. The value found for the kinetic energy release for this reaction, T 50 = (30.3 AE 2.1) meV, is slightly greater than that usually found for usual simple fission and is consistent with the process described.During the a → e decomposition, sulphur changes its valence state from 6 to 4, as one O atom from the SO 2 group migrates to the neutral fragment eliminated through a fivemembered transition state. The value found for the kinetic energy release, T 50 = (25.3 AE 1.8) meV corresponds to the range previously foun...

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Mass spectra interpretation of some thiophosphororganic compounds

Cited by 3 publications

References 6 publications

Electron impact mass spectral interpretation for some thiophosphoryl‐p‐acetylaminobenzenesulfonamides

Electron impact mass spectral interpretation for some thiophosphoryl‐p‐acetylaminobenzenesulfonamides

Electron ionisation mass spectral analysis and fragmentation pathways for some thiophosphorylicp‐carboxybenzene sulfonamides

Mass spectral study of the fragmentation pathways for some new thiophosphororganic molecules

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