Relationships between DFT/RRKM branching ratios of the complementary fragment ions [C5H5O]+ and [M - C 5H5O]+ and relative abundances in the EI mass spectrum of N-(2-furylmethyl)aniline

Journal of Physical Chemistry A

Volumn 116, Issue 49, 2012, Pages 12136-12147

  Vallejo Narváez, Wilmer E ^a   Bacca Villota, Paula V ^a   Solano Espinoza, Eduardo A ^a  

^a UNIVERSIDAD DE NARIÑO   (Colombia)

Author keywords

[No Author keywords available]

Indexed keywords

BOND CLEAVAGES; BRANCHING RATIO; DENSITY FUNCTIONAL THEORIES (DFT); ELECTRON IONIZATION MASS SPECTRA; ENERGY DEPENDENT; ENERGY PROFILE; FRAGMENT IONS; FRAGMENTATION PATHWAYS; ISOMERIC STRUCTURES; KINETIC BARRIER; MASS SPECTRA; MOLECULAR IONS; POTENTIAL ENERGY PROFILES; PYRYLIUM; RATE COEFFICIENTS; REACTION CHANNELS; REACTION MECHANISM; RELATIVE ABUNDANCE; RICE-RAMSPERGER-KASSEL-MARCUS;

ANILINE; BROMINE; CHEMICAL BONDS; CHLORINE; DENSITY FUNCTIONAL THEORY; ION SOURCES; ISOMERIZATION; ISOMERS; MASS SPECTROMETERS; MASS SPECTROMETRY; POTENTIAL ENERGY;

FLUORINE;

ANILINE DERIVATIVE; FURAN DERIVATIVE; ION; N (2 FURYLMETHYL)ANILINE; N-(2-FURYLMETHYL)ANILINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; QUANTUM THEORY;

ANILINE COMPOUNDS; FURANS; IONS; MOLECULAR STRUCTURE; QUANTUM THEORY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84870988971     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp306643r     Document Type: Article

References (30)

1. Kouznetsov, V. V.; Astudillo, L. S.; Vargas, L. Y.; Cazar, M. E. Synthesis of some secondary amine derivatives bearing a heteroaryl fragment J. Chil. Chem. Soc. 2004, 49, 319-325
2. Suvire, F. D.; Sortino, M.; Kouznetsov, V. V.; Vargas, L. Y.; Zacchino, S. A.; Mora, U.; Enriz, R. D. Structure-activity relationship study of homoallylamines and related derivatives acting as antifungal agents Bioorg. Med. Chem. 2006, 14, 1851-1862
3. Kouznetsov, V. V.; Vargas Méndez, L. Y.; Sortino, M.; Vásquez, Y.; Gupta, M. P.; Freile, M.; Enrize, R. D.; Zacchino, S. A. Antifungal and cytotoxic activities of some N-substituted aniline derivatives bearing a hetaryl fragment Bioorg. Med. Chem. 2008, 16, 794-809
4. Solano Espinoza, E. A.; Stashenko, E.; Martínez, J.; Mora, U.; Kouznetsov, V. Linear free energy relationships in C-N bond dissociations in molecular ions of 4-substituted N -(2-furylmethyl)anilines in the gas phase J. Mass Spectrom. 2007, 42, 1496-1503
5. + formation in the electron-impact mass spectra of 4-substituted N -(2-furylmethyl)anilines. Relative abundance prediction ability of the DFT calculations J. Mol. Struct. 2006, 769, 83-85
6. Spilker, R.; Grützmacher, H. F. Isomerization and fragmentation of methylfuran ions and pyran ions in the gas phase Org. Mass Spectrom. 1986, 21, 459-466
7. Solano Espinoza, E. A.; Vallejo Narváez, W. E. Density functional theory and RRKM calculations of the gas-phase unimolecular rearrangements of methylfuran and pyran ions before fragmentations J. Mass Spectrom. 2009, 44, 1452-1458
8. Solano Espinoza, E. A.; Vallejo Narváez, W. E. Density functional theory and RRKM calculations of decompositions of the metastable E -2,4-pentadienal molecular ions J. Mass Spectrom. 2010, 45, 722-733
9. Robin, D.; Sarraf, M.; Audier, H. E.; Fétizon, M. Isomerisation des ions alkyl-furannes et alkyl-pyrannes protones en phase gazeuse Tetrahedron Lett. 1984, 25, 3815-3818
10. Audier, H. E.; Robin, D. Competing rearrangement reactions of protonated methylfuran Org. Mass Spectrom. 1986, 21, 445-446
11. Eberlin, M. N.; Augusti, D. V.; Augusti, R. Mass Spectrometry and Gas-Phase Chemistry of Anilines. In Patai Series: The Chemistry of Anilines Part I; Rappaport, Z., Ed; Jonh Willey & Sons: Chichester, U.K., 2007; pp 293-345.
12. Nguyen, M. T. General and Theoretical Aspects of Anilines. In Patai Series: The Chemistry of Anilines Part I; Rappaport, Z., Ed; Jonh Willey & Sons: Chichester, U.K., 2007; pp 75-165.
13. Choe, J. C.; Cheong, N. R.; Park, S. M. Unimolecular dissociation of aniline molecular ion: A theoretical study Int. J. Mass Spectrom. 2009, 279, 25-31
14. Baer, T.; Hase, W. L. Unimolecular Reaction Dynamics: Theory and Experiments; Oxford University Press: New York, 1996; p 142.
15. Baer, T.; Carney, T. The dissociation dynamics of state selected metastable aniline ions by single and multiphoton ionization J. Chem. Phys. 1982, 76, 1304-1307
16. + from benzyl chloride and chlorotoluene molecular ions: A theoretical study J. Phys. Chem. A 2008, 112, 6190-6197
17. Qi, C.; Lin, Q.; Li, Y.; Pang, S.; Zhang, R. C-N bond dissociation energies: An assessment of contemporary DFT methodologies J. Mol. Struct. 2010, 961, 97-100
18. Zierkiewicz, W.; Komorowski, L.; Michalska, D. The amino group in adenine: MP2 and CCSD(T) complete basis set limit calculations of the planarization barrier and DFT/B3LYP study of the anharmonic frequencies of adenine J. Phys. Chem. B 2008, 112, 16734-16740
19. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.01; Gaussian, Inc.: Wallingford, CT, 2003.
20. Fukuy, K. A formulation of the reaction coordinate J. Phys. Chem. 1970, 74, 4161-4163
21. Scott, P. A.; Radom, L. Harmonic vibrational frequencies: An evaluation of Hartree-Fock, Moller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors J. Phys. Chem. 1996, 100, 16502-16513
22. Baer, T.; Mayer, P. Statistical Rice-Ramsperger-Kassel-Marcus quasiequilibrium theory calculation in mass spectrometry J. Am. Soc. Mass Spectrom. 1997, 8, 103-115
23. Baer, T.; Hase, W. L. Unimolecular Reaction Dynamics: Theory and Experiments; Oxford University Press: New York, 1996; p 206.
24. Drahos, L.; Vékey, K. MassKinetics: A theoretical model of mass spectra incorporating physical processes, reaction kinetics and mathematical descriptions J. Mass Spectrom. 2001, 36, 237-263
25. Helfferich, F. G. Kinetics of Multistep Reactions. In Comprehensive Chemical Kinetics; Green, N. J. B., Ed.; Elsevier B. V.: Amsterdam, The Netherlands, 2004; Vol. 8, pp 77-93.
26. MATHEMATICA; Wolfram Res. Inc.; Champaign, IL. Available from http://www.wolfram.com.
27. Baer, T.; Hase, W. L. Unimolecular Reaction Dynamics: Theory and Experiments; Oxford University Press: New York, 1996; pp 26-31, 131-133, 212-281.
28. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO, version 3.1; Gaussian, Inc.: Wallingford, CT.
29. Choe, J. C. Isomerization and dissociation of ethylbenzene and xylene molecular ions: A DFT study Chem. Phys. Lett. 2007, 435, 39-44
30. Choe, J. C. Dissociation of bromo- and iodotoluene molecular ions: A theoretical study Int. J. Mass Spectrom. 2008, 278, 50-58