Gas-Phase Smiles Rearrangement Reactions of Deprotonated 2-(4, 6-Dimethoxypyrimidin-2-Ylsulfanyl)-N-Phenylbenzamide and Its Derivatives in Electrospray Ionization Mass Spectrometry

Journal of the American Society for Mass Spectrometry

Volumn 18, Issue 10, 2007, Pages 1813-1820

  Zhou, Yuping ^a   Pan, Yuanjiang ^a   Cao, Xiaoji ^a   Wu, Jun ^a   Jiang, Kezhi ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

INTENSITY RATIOS; REARRANGEMENT REACTIONS; SUBSTITUENT CONSTANTS;

COMPUTATION THEORY; IONIZATION; ISOMERS; MASS SPECTROMETRY; NEGATIVE IONS;

DEPROTONATION;

2 (4,6 DIMETHOXYPYRIMIDIN 2 YLSULFANYL) N PHENYLBENZAMIDE; BENZAMIDE DERIVATIVE; ION; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLLISIONALLY ACTIVATED DISSOCIATION; CORRELATION ANALYSIS; DEPROTONATION; ELECTROSPRAY MASS SPECTROMETRY; ENERGY; GAS; INFRARED SPECTROMETRY; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; SMILE REARRANGEMENT REACTION; TANDEM MASS SPECTROMETRY;

BENZAMIDES; COMPUTER SIMULATION; GASES; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHASE TRANSITION; PROTONS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 34548670267     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2007.07.012     Document Type: Article

References (24)

1. Nezu Y., Miyazaki M., Sugiyama K., and Kajiwara I. Dimethoxypyrimidines as a Novel Herbicide. Part 1. Synthesis and Herbicidal Activity of Dimethoxyphenoxypyrimidines and Analogues. J. Pestic. Sci 47 (1996) 103-113
2. Nezu Y., Miyazaki M., Sugiyama K., and Kajiwara I. Dimethoxypyrimidines as a Novel Herbicide. Part 2. Synthesis and Herbicidal Activity of O-Pyrimidinylsalicylates and Analogues. J. Pestic. Sci 47 (1996) 115-124
3. Luthy C., Zondler H., Rapold T., Seifert G., Urwyler B., Heinis T., Steinrucken H.C., and Allen J. 7-(4,6-Dimethoxypyrimidinyl)Oxy and Thiophthalides as Novel Herbicides: Part 1. CGA 279 233: A new Grass-Killer for Rice. Pest. Manag. Sci 57 (2001) 205-224
4. Nezu Y., Wada N., Saitoh Y., Takahashi S., and Miyazawa T. Synthesis and Herbicidal activity of Pyrimidinyl Salicylic and Thiosalicylic Acids. J. Pestic. Sci 21 (1996) 293-303
5. Wu J., Chen M.F., Wang L.H., and Zhang P.Z. 2-(4,6-Dimethoxypyrimidin-2-Ylsulfanyl) -N-Phenylbenzamide. Acta Crystallogr. E E61 (2005) o3728-o3729
6. Busch K.L., Glish G.L., and McLuckey S.A. Mass Spectrometry/ Mass Spectrometry: Techniques and Applications of Tandem Mass Spectrometry (1988), VCH Publishers, New York 53
7. Lobodin V.V., Ovcharenko V.V., Pihlaja K., Morzherin Y.Y., and Lebedev A.T. "Tert-Amino Effect" Induced by Electron Ionization and Comparison with Thermal Reaction in Solution. Rapid Commun. Mass Spectrom 18 (2004) 724-728
8. Glish G.L., and Cooks R.G. The Fischer Indole Synthesis and Pinacol Rearrangement in the Mass Spectrometer. J. Am. Chem. Soc 100 (1978) 6720-6725
9. Wang H.Y., Zhang X., and Guo Y.L. Using Tandem Mass Spectrometry to Predict Chemical Transformations of 2-Pyrimidinyloxy-N-Arylbenzyl Amine Derivatives in Solution. J. Am. Soc. Mass Spectrom 17 (2006) 253-263
10. Lin H.Y., Ridge D.P., Uggerud E., and Vulpius T. Unimolecular Chemistry of Protonated Formamide. Mass Spectrometry and ab Initio Quantum Chemical Calculations. J. Am. Chem. Soc 116 (1994) 2996-3004
11. Tu Y.P., and Harrison A.G. Fragmentation of Protonated Amides Through Intermediate Ion-Neutral Complexes: Neighboring Group Participation. J. Am. Soc. Mass Spectrom 9 (1998) 454-462
12. Warren L.A., and Smiles S. Iso-β-Naphthol Sulphide. J. Chem. Soc (1930) 956
13. Truce W.E., Kreider E.M., and Brand W.W. The Smiles and Related Rearrangements of Aromatic Systems. Org. React 18 (1970) 99-215
14. Eichinger P.C.H., Bowie J.H., and Hayes R.N. The Gas-Phase Smiles Rearrangement: A Heavy Atom Labeling Study. J. Am. Chem. Soc 111 (1989) 4224-4227
15. 18O Labelling Study. Org. Mass Spectrom 27 (1992) 995-999
16. Eichinger P.C.H., Dua S., and Bowie J.H. A Comparison of Skeletal Rearrangement Reactions of Even-Electron Anions in Solution and in the Gas Phase. Int. J. Mass Spectrom. Ion Processes 133 (1994) 1-12
17. Wang F. Collision-Induced Gas-Phase Smiles Rearrangement in Phenoxy-N-Phenylacetamide Derivatives. Rapid Commun. Mass Spectrom 20 (2006) 1820-1821
18. Hiserodt R.D., Pope B.M., Cossette M., and Dewis M.L. Proposed Mechanisms for the Fragmentation of Doubly Allylic Alkenamides (Tingle Compounds) by Low Energy Collisional Activation in a Triple Quadrupole Mass Spectrometer. J. Am. Soc. Mass Spectrom 15 (2004) 1462-1470
19. Filho E.R., Almeida A.M.P., and Tabak M. Fragmentation of Dipyridamole and Related Dipyrimidines by ESI-CAD Mass Spectrometry. J. Mass Spectrom 38 (2003) 540-547
20. Makowiecki J., Tolonen A., Uusitalo J., and Jalonen J. Cone Voltage and Collision Cell Collision-Induced Dissociation Study of Triphenylethylenes of Pharmaceutical Interest. Rapid Commun. Mass Spectrom 15 (2001) 1506-1513
21. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M.E., Replogle S., and Pople J.A. Gaussian 03 (2003), Gaussian Inc, Pittsburgh, PA
22. Bowie J.H. The Fragmentation of Even-Electron Organic Negative Ion. Mass Spectrom. Rev 9 (1990) 349-379
23. Smith M.B. Organic Synthesis (2002), McGraw-Hill, New York 164-166
24. Hansch C., Leo A., and Taft R.W. A Survey of Hammett Substituent Constant and Resonance and Field Parameters. Chem. Rev 91 (1991) 165-195