Loss of benzene to generate an enolate anion by a site-specific double-hydrogen transfer during CID fragmentation of o-alkyl ethers of ortho-hydroxybenzoic acids

Journal of Mass Spectrometry

Volumn 43, Issue 9, 2008, Pages 1224-1234

  Attygalle, Athula B ^a   Bialecki, Jason B ^a   Nishshanka, Upul ^a   Weisbecker, Carl S ^a   Ruzicka, Josef ^a  

^a Stevens Institute of Technology   (United States)

Author keywords

Alkyloxybenzoic acid; CID; ESI; Even electron ions; Fragmentation; Ion neutral complex; Isotope effect; Negative ions; Ortho effect

Indexed keywords

ACIDS; BENZENE; ETHERS; HYDROGEN; NEGATIVE IONS; NONMETALS; ORGANIC COMPOUNDS;

ALKYL ETHERS; ALKYLOXYBENZOIC ACID; CID; COLLISION-INDUCED DISSOCIATION; ENOLATE; ENOLATE ANIONS; ESI; EVEN-ELECTRON IONS; FRAGMENTATION; HYDROGEN TRANSFERS; INITIAL LOSSES; ION NEUTRAL COMPLEX; ISOTOPE EFFECT; ORTHO EFFECT; SITE-SPECIFIC;

IONS;

ALKYL ETHER; ANION; BENZENE; BENZOIC ACID DERIVATIVE; DEUTERIUM; HYDROGEN; SALICYLIC ACID;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; COLLISIONALLY ACTIVATED DISSOCIATION; ELECTRON; ELECTROSPRAY MASS SPECTROMETRY; GAS CHROMATOGRAPHY; ISOMER; ISOTOPE LABELING; KINETICS; MASS SPECTROMETER; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; QUANTUM MECHANICS; SYNTHESIS; THERMODYNAMICS;

EID: 52649177674     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1399     Document Type: Article

References (38)

1. Hill AW, Mortishire-Smith RJ. Automated assignment of high-resolution collisionally activated dissociation mass spectra using a systematic bond disconnection approach. Rapid Communications in Mass Spectrometry 2005;19: 3111.
2. HighChem, Slovak Republic. http://www.highchem.com [accessed 2007].
3. Beynon JH, Saunders RA, Williams AE. The high resolution mass spectra of aliphatic esters. Analytical Chemistry 1961;33: 221.
4. Kingston DGI, Bursey IT, Bursey MM. Intramolecular hydrogen transfer in mass spectra. II. The McLafferty rearrangement and related reactions. Chemical Reviews 1974;74: 215.
5. Attygalle AB, Garcia-Rubio S, Ta J, Meinwald J. Collisionally-induced dissociation mass spectra of organic sulfate anions. Journal of Chemical Society, Perkin Transactions 2 2001; 498.
6. Attygalle AB, Ruzicka J, Varughese D, Bialecki JB, Jafri S. Low-energy collision-induced fragmentation of negative ions derived from ortho-, meta-, and para-hydroxyphenyl carbaldehydes, ketones, and related compounds, Journal of Mass Spectrometry 2007;42: 1207.
7. Alconcel LS, Deyerl H-J, Continetti RE. Effects of alkyl substitution on the energetics of enolate anions and radicals. Journal of the American Chemical Society 2001;123: 12675.
8. Zibuck R, Streiber J. 4-Pentenoic acid, 3-oxo-, ethyl ester. Organic Synthesis 1993;71: 236.
9. Paquette LA, Earle MJ, Smith GF. (4R)-(+)-terf-Butyldimethyl siloxy-2-cyclopenten-l-one. Organic Synthesis 1996;73: 36.
10. Marco JL. Chiral precursors for syntheses of furanoterpenes. Tetrahedron 1989;45: 1475.
11. Abad J-L, Fabrias G, Camps F. Synthesis of dideuterated and enantiomers of monodeuterated tridecanoic acids at -9 and C-10 positions. Journal of Organic Chemistry 2000;65: 8582.
12. ercero JM, Matxain JM, Lopez X, York DM, Largo A, riksson LA, UgaldeJM. Theoretical methods that help nderstanding the structure and reactivity of gas phase ions. International journal of Maim Spectrometry 2005;240: 37.
13. Ditchfield R, Hehre WJ, I'opleJA. Self-consistent molecular-orbital methods. IX. An extended Gaussian-type basis for molecular studies of organic molecules. Journal of Chemical Physics 1971;54: 724.
14. Chowdhury SK, Harrison AC Fragmentation reactions of some deprotonated acetophenones. Organic Mass Spectrometry 1990;25: 637.
15. Reeks LB, EichingerCH, Bowie JH. Ortho-rearrangements of o-alkylphenoxide anions. Rapid Communications in Mass Spectrometry 1993;7: 286.
16. + with M = H, Li, Na, K, Rb, Ag, and Cs. International Journal of Mass Spectrometry 2004;233: 103.
17. Gross ML. Charge-remote fragmentation: an account of research on mechanisms and applications. International journal of Mass Spectrometry 2000;200: 611.
18. Tomer KB, Crow FW, Gross ML. Location of double bond position in unsaturated fatty acids by negative ion MS/MS. Journal of the American Chemical Society 1983;105: 5487.
19. Jensen NJ, Tomer KB, Gross ML. Gas-phase ion decompositions occurring remote to a charge site. Journal of the American Chemical Society 1985;107: 1863.
20. Chen G, Pramanik BN, Bartner PL, Saksena AK, Gross ML. Multiple-stage mass spectrometric analysis of complex oligosaccharide antibiotics (Everninomicins) in a quadrupole ion trap. Journal of the American Society for Mass Spectrometry 2002;13: 1313.
21. Tomazela DM, Sabino AA, Sparrapan R, Gozzo FC, Eberlin MN. Distonoid ions. Journal of the American Society for Mass Spectrometry 2006;17: 1014.
22. Gozzo FC, Moraes AB, Eberlin MN, Laali KK. The first nonclassical distonic ion. Journal of the American Chemical Society 2000;122: 7776.
23. Stirk KM, Kiminkinen LKM, Kenttämaa HI. Ion-molecule reactions of distonic radical cations. Chemical Revieios 1992;92: 1649.
24. 2CIH) ylides by neutralization-reionization mass spectrometry: a theoretical prediction. Journal of the American Chemical Society 1984;106: 5805.
25. Yates BF, Bouma WJ, Radom L. Distonic radical cations. Guidelines for the assessment of their stability. Tetrahedron 1986;42: 6225.
26. Hill BT, Poutsma JC, Chyall LJ, Hu J, Squires RR. Distonic ions of the "ate" class. Journal of the American Society for Mass Spectrometry 1999;10: 896.
27. Thoen KK, Smith RL, Nousiainen JJ, Nelson ED, Kenttämaa HI. Charged phenyl radicals. Journal of the American Chemical Society 1996;118: 8669.
28. Crews P, Rodriguez J, Jaspars M. Organic Structure Analysis. Oxford University Press: Oxford, 1998; 246.
29. Kami M, Mandelbaum A. The 'even-electron rule'. Organic Mass Spectrometry 1980;15: 53.
30. Krauss D, Mainx HG, Tauscher B, Bischof P. Fragmentation of trimethylsilyl derivatives of 2-alkoxyphenols: a further violation of the 'even-electron rule'. Organic Mass Spectrometry 1985;20: 614.
31. McLafferty FW, Tureček F. Interpretation of Mass Spectra. University Science Books: Mill Valley, 1993.
32. Schwarz H. Some newer aspects of mass spectrometric ortho effects. Topics in Current Chemistry 1978;73: 231.
33. Reddy PN, Srikanth R, Venkateswarlu N, Rao NR, Srinivas R. Electrospray ionization tandem mass spectrometric study of three isomeric substituted aromatic sulfonic acids; differentiation via ortho effects. Rapid Communications in Mass Spectrometry 2005;19: 72.
34. Moraes LAB, Sabino AA, Meurer EC, Eberlin MN. Absolute configuration assignment of ortho, meta, or para isomers by mass spectrometry. Journal of the American Society for Mass Spectrometry 2005;16: 431.
35. Xiaolan C, Lingbo Q, Jiansha L, Lei G, Youzhu Y, Yufen Z. Ortho effects in bis-phosphoric esters of the dihydroxy- and aminohydroxybenzenes observed by ESI-MS/MS. Journal of Mass Spectrometry Society of Japan 2004;2: 63.
36. Benz W, Biemann K. The specificity of the electron-impact induced elimination of water from alcohols and related reactions in the mass spectrometer. Journal of the American Chemical Society 1964;86: 2375.
37. Djerassi C, Fenselau C. Mass spectrometry in structural and stereochemical problems. LXXXVI. The hydrogen-transfer reactions in butyl propionate, benzoate, and phthalate. Journal of the American Chemical Society 1965;87: 5756.
38. Benoit FM, Harrison AG. Hydrogen migrations in mass spectrometry. Single and double hydrogen migrations in the electron impact fragmentation of n-propyl benzoate. Organic Mass Spectrometry 1976;11: 1056.