The ESI CAD fragmentations of protonated 2,4,6-tris(benzylamino)- and tris(benzyloxy)-1,3,5-triazines involve benzyl-benzyl interactions: A DFT study

Journal of Mass Spectrometry

Volumn 47, Issue 7, 2012, Pages 860-868

  Ramesh, M ^a   Raju, B ^a   George, M ^b   Srinivas, K ^a,c   Jayathirtha Rao, V ^a,c   Bhanuprakash, K ^a   Srinivas, R ^a,c  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b SACRED HEART COLLEGE   (India)

^c NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

benzyl benzyl interactions; DFT calculations; electrospray ionization; substituted triazines; tandem mass spectrometry

Indexed keywords

BENZYL CATIONS; BENZYL GROUP; COLLISION ENERGIES; COLLISIONALLY ACTIVATED DISSOCIATION; DENSITY FUNCTIONAL THEORY CALCULATIONS; DFT CALCULATION; DFT STUDY; FRAGMENTATION PROCESS; HIGH ENERGY; HIGH RESOLUTION MASS SPECTROMETRY; MASS SPECTRA; P-XYLENE; PROTONATED; PROTONATED MOLECULES; RING CARBONS; SUBSTITUTED TRIAZINES; TANDEM MASS SPECTROMETRY;

BENZENE; CARBON; DENSITY FUNCTIONAL THEORY; DEUTERIUM; DISSOCIATION; ELECTROSPRAY IONIZATION; MASS SPECTROMETRY; MOLECULES; OLEFINS; POSITIVE IONS; STYRENE; TOLUENE; XYLENE;

PROTONATION;

2,4,6 TRIS(BENZYLAMINO) 1,3,5 TRIAZINE; 2,4,6 TRIS(BENZYLOXY) 1,3,5 TRIAZINE; 3,6 DIMETHYLENECYCLOHEXA 1,4 DIENE; ALKADIENE; BENZENE; CARBON; CATION; DEUTERIUM; HYDROGEN; ION; PARA XYLENE; STYRENE; TOLUENE; TRIAZINE; UNCLASSIFIED DRUG;

ARTICLE; COLLISIONALLY ACTIVATED DISSOCIATION; DENSITY FUNCTIONAL THEORY; DISSOCIATION; ELECTRON SPIN RESONANCE; ENERGY; FRAGMENTATION REACTION; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTON TRANSPORT; STRUCTURE ANALYSIS;

BENZYL COMPOUNDS; IONS; QUANTUM THEORY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY; TRIAZINES;

EID: 84863970309     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.3037     Document Type: Article

References (52)

1. R. Menicagli, S. Samaritani, G. Signore, F. Vaglini, L. D. Via,. Triazine derivatives and their therapeutical applications. J. Med. Chem. 2004, 47, 4649.
2. V. K. Pandey, S. Tusi, Z. Tusi, M. Joshi, S. Bajpai,. Synthesis and biological activity of substituted 2,4,6-s-triazines. Acta Pharm. 2004, 54, 1.
3. (a), Z. Brzozowski, F. Saczewski, M. Gdaniec,. Synthesis, structural characterization and antitumor activity of novel 2,4-diamino-1,3,5-triazine derivatives. Eur. J. Med. Chem. 2000, 35, 1053
4. (b), K. Sztanke, K. Pasternak, J. Rzymowska, M. Sztanke, M. K. Szerszen,. Synthesis, structure elucidation and identification of antitumoural properties of novel fused 1,2,4-triazine aryl derivatives. Eur. J. Med. Chem. 2008, 43, 1085.
5. (a), P. Verite, D. Andre, S. Menager, O. Lafont,. Gas chromatographic-mass spectrometric method for analysis of a pyrimido-s-triazine and some of its metabolites in dog urine. J. Chromatogr. Biomed. Appl. 1992, 578, 134
6. (b), S. Menager, C. Loire, O. Lafont, B. Champeyrol, C. Delabos, J. Garnier, C. C. Farnoux,. Synthèse et étude de l'activité antimicrobienne de dérivés diversement chlorés du squelette 3-phényloctahydropyrimido [3,4-a]-s-triazine. Eur. J. Med. Chem. 1991, 26, 79
7. (c), J. C. A. Hunt, E. Briggs, E. D. Clarke, W. G. Whittingham,. Synthesis and SAR studies of novel antifungal 1,2,3-triazines. Bioorg. Med. Chem. Lett. 2007, 17, 5222.
8. J. P. Whitten, Y. F. Xie, P. E. Erickson, T. R. Webb, E. B. DeSouza, D. E. Grigoriasdis, J. R. McCarty,. Rapid microscale synthesis, a new method for lead optimization using robotics and solution phase chemistry: application to the synthesis and optimization of corticotropin-releasing factor receptor antagonists. J. Med. Chem. 1996, 39, 4354.
9. B. R. Henke, T. G. Consler, N. Go, R. Hohman, S. A. Jones, A. T. Lu, L. B. Moore, J. T. Moore, L. A. O. Miller, R. G. Robinett, J. Shearin, P. K. Spearing, L. Stewart, P. S. Turnball, S. L. Wearver, S. P. Willams, G. B. Wisely, M. H. Lambart,. A new series of estrogen receptor modulators that display selectivity for estrogen receptor β. J. Med. Chem. 2002, 45, 5492.
10. J. L. Seffernick, H. M. Tavish, J. P. Osborne, M. L. Souza, M. J. Sadowsky, L. P. Wackett,. Atrazine chlorohydrolase from Pseudomonas Sp. strain ADP is a metalloenzyme. Biochemistry 2002, 41, 14430.
11. (a), V. R. Thalladi, S. Brasselet, H. C. Weiss, D. Blaser, A. K. Katz, H. L. Carrell, R. Boese, J. Zyss, A. Nangia, G. R. Desiraju,. Crystal engineering of some 2,4,6-triaryloxy-1,3,5-triazines: octupolar nonlinear materials. J. Am. Chem. Soc. 1998, 120, 2563
12. (b), W. Zhu, G. S. Wu,. Molecular design for octupolar nonlinear optical systems: an ab initio study of first hyperpolarizabilities of symmetrically heteroaromatic-substituted triazines. J. Phys. Chem. A 2001, 105, 9568
13. (c), V. J. Rao, K. Bhanuprakash,. Computational studies of the non-linear optical properties of some three-dimensional molecules: effect of π-Ï-π through bond interaction on the first hyperpolarizability. Synth. Metals 2003, 132, 315.
14. W. Witte,. Antibiotic resistance in gram-positive bacteria: epidemiological aspects. J. Antimicrob. Chemother. 1999, 44A, 1.
15. P. Tsitsa, E. Antoniadou-Vyza, S. J. Hamodrakas, E. E. Eliopoulos, A. Tsantili-Kakoulidou, E. Lada-Hytiroglou, C. Roussakis, I. Chinou, A. Hempel, N. Camerman, F. P. Ottensmeyer, D. A. Vanden Berghe,. Synthesis, crystal structure and biological properties of new series of lipophilic s-triazines, dihydrofolate reductase inhibitors. Eur. J. Med. Chem. 1993, 28, 149.
16. A. Solankee, K. Kapadia, A. Ciric, M. Sokovic, I. Doytchinova, A. Geronikaki,. Synthesis of some new s-triazine based chalcones and their derivatives as potent antimicrobial agents. Eur. J. Med. Chem. 2010, 45, 510.
17. G. A. McKay, R. Reddy, F. Arhin, A. Belley, D. Lehoux, G. Moeck, I. Sarmiento, T. R. Parr, P. Gros, J. Pelletier, A. R. Far,. Triaminotriazine DNA helicase inhibitor with antibacterial activity. Bioorg. Med. Chem. Lett. 2006, 16, 1286.
18. A. Ghaib, S. Menager, P. Verite, O. Lafont,. Synthesis of variously 9,9-dialkylated octahydropyrimido [3,4-a]-s-triazines with potential antifungal activity. II Farmaco 2002, 57, 109.
19. S. Lebreton, N. Newcombe, M. Bradley,. Antibacterial single-bead screening. Tetrahedron 2003, 59, 10213.
20. V. V. Malwad, J. M. Shirodkar,. Synthesis of biologically active thiazolo-benzopyranyl-s-triazine derivatives. Ind. J. Chem. 2003, 42B, 621.
21. (a), K. Sinivas, U. Srinivas, V. Jayathirtha Rao, K. Bhanuprakash, K. Harikishore, U. S. N. Murthy,. Synthesis and antibacterial activity of 2,4,6-tri substituted s-triazines. Bioorg. Med. Chem. Lett. 2005, 15, 1121
22. (b), K. Srinivas, U. Srinivas, K. Bhanuprakash, K. Harikishore, U. S. N. Murthy, V. Jayathirtha Rao,. Synthesis and antibacterial activity of various substituted s-triazines. Eur. J. Med. Chem. 2006, 41, 1240
23. (c), K. Sinivas, S. Sitha, B. Sridhar, V. Jayathirtha Rao, K. Bhanuprakash, K. Ravikumar,. Tautomerism of bis(2,4,-benzyloxy)-6-5(H)-one-1,3, 5-triazine: a combined crystallographic and quantum-chemical investigation. Struct. Chem. 2006, 17, 561.
24. A. Vincze, J. Yinon,. Tandem mass spectrometric collision-induced dissociation study of s-triazines in an ion trap mass spectrometer. J. Mass Spectrom. 1997, 32, 1320.
25. P. N. Preston, W. Steedman, M. H. Palmer, M. S. M. Mackenzie, M. F. G. Stevens,. The mass spectra of s-triazines. Org. Mass Spectrom. 1970, 3, 863.
26. M. Sochacki, Z. J. Kami,. Mass spectrometric study of 2-acyloxy-4,6-dimethoxy-1,3,5-triazines. Org. Mass Spectrom. 1994, 29, 102.
27. Y. J. Kim, J. C. Choe, M. S. Kim,. Tandem mass spectrometry of s-triazine herbicides. Bull. Korean Chem. Soc. 1989, 10, 15.
28. P. T. Kaye, X. W. Nocanda,. Fragmentation patterns in the electron impact mass spectra of 1,3,5-triazin-2-one derivatives. Arkivoc 2000, (vi), 923.
29. G. Giorgi, A. P. Piccionello, A. Pace, S. Buscemi,. Hydration/elimination reactions of trapped protonated fluoroalkyl triazines. J. Mass Spectrom. 2008, 43, 265.
30. A. Vincze, J. Yinon, T. Peres, C. Lifshitz,. Doubly charged ions in the electron ionization mass spectra of 4,6-di(substituted)amino s-triazines. Int. J. Mass Spectrom. 1999, 192, 99.
31. O. Martiskainen, K. Sztanke, D. Matosiuk, K. Pihlaja,. Electron ionization mass spectra of 8-aryl-3,4-dioxo-2H,8H-6,7-dihydroimidazo[2,1-c][1,2, 4]triazines. Do they exhibit tautomerism in the gas phase? Rapid Commun. Mass Spectrom. 2006, 20, 2548.
32. G. Giorgi, A. P. Piccionello, A. Pace, S. Buscemib,. Gas phase behavior of radical cations of perfluoroalkyl-1,2,4-triazines: an experimental and theoretical study. J. Mass Spectrom. 2009, 44, 1369.
33. E. M. Thurman, I. Ferrer, O. J. Pozo, J. V. Sancho, F. Hernandez,. The even-electron rule in electrospray mass spectra of pesticides. Rapid Commun. Mass Spectrom. 2007, 21, 3855.
34. M. H. Palmer, P. N. Preston, M. F. G. Stevens,. The mass spectra of 1,2,4-triazines and related compounds. Org. Mass Spectrom. 1971, 5, 1085.
35. J. A. Ross, B. G. Tweedy,. Mass spectra of chloro-, aminochloro- and ethyl amino chloro-s-triazines. Org. Mass Spectrom. 1970, 3, 219.
36. S. Foti, R. Saletti, F. Russo, A. Santagati, M. Santagati,. Structural characterization of 1,3,4-thiadiazolo[3,2-a][1,3,5]triazines by electron impact mass spectrometry. Org. Mass Spectrom. 1989, 24, 379.
37. J. Clark,. Heterocyclic studies-XXVIII: mass spectra of some 5-trifluoromethyl pyrimido-(5,4-E)AS-triazines. Org. Mass Spectrom. 1972, 6, 467.
38. R. A. Corral, O. O. Orazi,. Mass spectra of heterocyclic compounds.II-Hexahydro-1,3,5,-triazines. Org. Mass Spectrom. 1976, 11, 1221.
39. J. Clark,. Heterocyclic studies-XXIX: mass spectra of some 1,2-dihydro-5-trifluoromethyl-pyrimido(5,4-E)AS-triazines. Org. Mass Spectrom. 1973, 7, 225.
40. G. M. Titato, R. C. Bicudo, F. M. Lanças,. Optimization of the ESI and APCI experimental variables for the LC/MS determination of s-triazines, methyl carbamates, organophosphorous, benzimidazoles, carboxamide and phenylurea compounds in orange samples. J. Mass Spectrom. 2007, 42, 1348.
41. G. Giorgi, A. P. Piccionello, A. Pace, S. Buscemi,. Effect of protonation and deprotonation on the gas-phase reactivity of fluorinated 1,2,4-triazines. J. Am. Soc. Mass Spectrom. 2008, 19, 686.
42. W. L. Budde,. Analytical mass spectrometry of herbicides. Mass Spectrom. Rev. 2004, 23, 1.
43. J. M. Garver, Z. Yang, S. Kato, S. W. Wren, K. M. Vogelhuber, W. C. Lineberger, V. M. Bierbaum,. Gas phase reactions of 1,3,5-triazine: proton transfer, hydride transfer, and anionic Ï-adduct formation. J. Am. Soc. Mass Spectrom. 2011, 22, 1260.
44. + ions of dibenzyl esters upon chemical ionization and collision induced dissociation conditions. J. Mass Spectrom. 1997, 32, 515.
45. M. Edelson-Averbuck, A. Etinger, A. Mandelbaum,. Intramolecular benzyl-benzyl in protonated benzyl diethers in the gas phase. Effects of internal hydrogen bonding. J. Chem. Soc., Perkin Trans. 1999, 2, 1095.
46. M. Edelson-Averbuck, A. Mandelbaum,. Gas-phase intramolecular benzyl-benzyl interactions in protonated dibenzyl derivatives containing benzyl-oxygen, -sulfur and -nitrogen bonds. J. Chem. Soc., Perkin Trans. 2000, 2, 989.
47. M. Edelson-Averbuck, A. Mandelbaum,. Intramolecular electrophilic aromatic substitution in gas-phase-protonated difunctional compounds containing one or two arylmethyl groups. J. Mass Spectrom. 2003, 38, 1169.
48. Y. Chai, H. Sun, Y. Pan, C. Sun,. N-centered odd-electron ions formation from collision-induced dissociation of electrospray ionization generated even-electron ions: single electron transfer via ion/neutral complex in the fragmentation of protonated N,N'-dibenzylpiperazines and protonated N-benzylpiperazines. J. Am. Soc. Mass Spectrom. 2011, 22, 1526.
49. J. Bialecki, J. Ruzicka, A. B. Attygalle,. An unprecedented rearrangement in collision-induced mass spectrometric fragmentation of protonated benzylamines. J. Mass Spectrom. 2006, 41, 1195.
50. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox,. Gaussian 09, Revision A.1, Gaussian, Inc.: Wallingford CT, 2009.
51. Y. Chai, K. Jiang, Y. Pan,. Hydride transfer reactions via ion-neutral complex: fragmentation of protonated N-benzylpiperidines and protonated N-benzylpiperazines in mass spectrometry. J. Mass Spectrom. 2010, 45, 496.
52. D. Kuck, H.-F. Grützmacher, D. Barth, S. Heitkamp, M. C. Letzel,. The Role of ion/neutral complexes in the fragmentation of N-benzyl- (alkylpyridinium) ions. Int. J. Mass Spectrom. 2011, 306, 159.