Electrospray ionization (ESI) fragmentations and dimethyldioxirane reactivities of three diverse lactams having full, half, and zero resonance energies

Journal of Organic Chemistry

Volumn 79, Issue 2, 2014, Pages 517-528

  Morgan, Kathleen M ^a   Ashline, David J ^b   Morgan, Jessica P ^c   Greenberg, Arthur ^c  

^a XAVIER UNIVERSITY OF LOUISIANA   (United States)

^b UNIVERSITY OF NEW HAMPSHIRE   (United States)

^c University of New Hampshire   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROSPRAY IONIZATION; HYDROGEN BONDS; MASS SPECTROMETRY; PROTONATION; RESONANCE;

DFT CALCULATION; DIMETHYLDIOXIRANE; ELECTROSPRAY IONIZATION (ESI); ELECTROSPRAY IONIZATION MASS SPECTROMETRY; FRAGMENTATION PATHWAYS; INTRAMOLECULAR HYDROGEN BONDING; N-OXIDES; RESONANCE ENERGIES;

AMIDES;

1 AZABICYCLO[3.3.1]NONAN 2 ONE; 2,2 DIHYDROXY N OXIDE; 3,5,7 TRIMETHYL 1 AZAADAMANTAN 2 ONE; DIMETHYLDIOXIRANE; ETHYL 2 PYRROLIDINONE; LACTAM DERIVATIVE; OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL REACTION; DENSITY FUNCTIONAL THEORY; ELECTROSPRAY MASS SPECTROMETRY; FRAGMENTATION REACTION; HYDRATION; HYDROGEN BOND; PROTON TRANSPORT; TAUTOMER;

EPOXY COMPOUNDS; LACTAMS; MOLECULAR STRUCTURE; QUANTUM THEORY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; THERMODYNAMICS;

EID: 84896741415     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402041u     Document Type: Article

References (66)

1. Pauling, L. The Nature of the Chemical Bond; Cornell University Press: Ithaca, NY, 1939.
2. Greenberg, A., Breneman, C. M., Liebman, J. F., Eds. The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science; J. Wiley & Sons: New York, 2003.
3. Wiberg, K. B. In The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science; Greenberg, A., Breneman, C. M., Liebman, J. F., Eds.; J. Wiley & Sons: New York, 2003; p 33.
4. Mucsi, Z.; Tsai, A.; Szori, M.; Chass, G. A.; Viscolcz, B.; Csizmadia, I. G. J. Phys. Chem. A 2007, 111, 13245.
5. Glover, S. A.; Rosser, A. A. J. Org. Chem. 2012, 77, 5492.
6. Szostak, M.; Aube, J. Chem. Rev. 2013, 113, 5701.
7. Birchall, T.; Gillespie, R. J. Can. J. Chem. 1963, 41, 2642.
8. Olah, G. A.; White, A. M. Chem. Rev. 1970, 70, 561.
9. Klumpp, D. A.; Rendy, R.; Zhang, Y.; Gomez, A.; McElrea, A. Org. Lett. 2004, 6, 1789.
10. Greenberg, A.; Venanzi, C. A. J. Am. Chem. Soc. 1993, 115, 6951.
11. Greenberg, A.; Moore, D. T.; DuBois, T. D. J. Am. Chem. Soc. 1996, 118, 8658.
12. Werstiuk, N. H.; Brown, R. S.; Wang, Q. Can. J. Chem. 1996, 74, 524.
13. Mujika, J. I.; Mercero, J. M.; Lopez, X. J. Phys. Chem. A 2003, 107, 6099.
14. Mujika, J. I.; Mercero, J. M.; Lopez, X. J. Am. Chem. Soc. 2005, 127, 4445.
15. Perrin, C. L. Acc. Chem. Res. 1989, 22, 268.
16. Pracejus, H. Chem. Ber. 1959, 92, 988.
17. Pracejus, H.; Kehlen, M.; Kehlen, H.; Matschiner, H. Tetrahedron 1965, 21, 2257.
18. Blackburn, G. M.; Skaife, C. J.; Kay, I. T. J. Chem. Res. Miniprint 1980, 3650.
19. Somayaji, V.; Brown, R. S. J. Org. Chem. 1986, 51, 2676.
20. Brown, R. S.; Bennet, A. J.; Slebocka-Tilk, H. Acc. Chem. Res. 1992, 25, 481.
21. Tani, K.; Stoltz, B. M. Nature 2006, 441, 731.
22. Ly, T.; Krout, M.; Pham, D. K.; Tani, K.; Stoltz, B. M.; Julian, R. R. J. Am. Chem. Soc. 2007, 129, 1864.
23. Kirby, A. J.; Komarov, I. V.; Wothers, P. D.; Feeder, N. Angew. Chem., Int. Ed. 1998, 37, 785.
24. Kirby, A. J.; Komarov, I. V.; Feeder, N. J. Am. Chem. Soc. 1998, 120, 7101.
25. Kirby, A. J.; Komarov, I. V.; Feeder, N. J. Chem. Soc., Perkin Trans. 2 2001, 522.
26. Morgan, K. M.; Rawlins, M. L.; Montgomery, M. N. J. Phys. Org. Chem. 2005, 18, 310.
27. Doering, W. E.; Chanley, J. D. J. Am. Chem. Soc. 1946, 68, 586
28. (ref 12). We thank an anonymous reviewer of this paper for directing our attention to this reference citing Woodward's study.
29. Woodward, R. B.; Neuberger, A.; Trenner, N. R. In The Chemistry of Penicillin; Clarke, H. T., Johnson, J. R., Robinson, R., Eds.; Princeton University Press: Princeton, NJ, 1949; pp 415-439.
30. Crowfoot, D.; Bunn, C. W.; Rogers-Low, B. W.; Turner-Jones, A. In The Chemistry of Penicillin; Clarke, H. T., Johnson, J. R., Robinson, R., Eds.; Princeton University Press: Princeton, NJ, 1949; pp 310-367.
31. Dunitz, J. D.; Winkler, R. K. Acta Crystallogr., Sect. B 1975, 31, 251.
32. Werstiuk, N. H.; Muchall, H. M.; Roy, C. D.; Ma, J.; Brown, R. S. Can. J. Chem. 1998, 76, 672.
33. Sliter, B.; Morgan, J.; Greenberg, A. J. Org. Chem. 2011, 76, 2770.
34. Morgan, J.; Greenberg, A. J. Phys. Org. Chem. 2012, 25, 1422.
35. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. J. Phys. Chem. Ref. Data, Suppl. 1988, 17 (Suppl. No. 1), 321.
36. Coskun, N.; Cetin, M. Tetrahedron Lett. 2004, 45, 8973.
37. Annese, C.; D'Accolti, L.; De Zotti, M.; Fusco, C.; Toniolo, C.; Williard, P. G.; Curci, R. J. Org. Chem. 2010, 75, 4812.
38. Greenberg, A.; DuBois, T. D. J. Mol. Struct. 2001, 567-568, 303.
39. Lin, H-Y; Ridge, D. P.; Uggerud, E.; Vulpius, T. J. Am. Chem. Soc. 1994, 116, 2996.
40. Crotti, A. E. M.; Fonseca, T.; Hong, H.; Staunton, J.; Galembeck, S. E.; Lopes, N. P.; Gates, P. J. Int. J. Mass Spectrom. 2004, 232, 271.
41. Vessecchi, R.; Galembeck, S. E. J. Phys. Chem. A 2008, 112, 4060.
42. Tu, Y.-P. Rapid Commun. Mass Spectrom. 2004, 18, 1345.
43. Divito, E. B.; Davic, A. P.; Johnson, M. E.; Cascio, M. Anal. Chem. 2012, 84, 2388.
44. Hall, H. K., Jr.; Shaw, R. G.; Deutschmann, A. J. Org. Chem. 1980, 45, 3722.
45. Hall, H. K., Jr.; El-Shekeil, A. Chem. Rev. 1983, 83, 549.
46. Buchanan, G. L. J. Chem. Soc., Chem. Commun. 1981, 814.
47. Steliou, K.; Poupart, M. A. J. Am. Chem. Soc. 1983, 105, 7130.
48. Brehm, R.; Ohnhauser, D.; Gerlach, H. Helv. Chim. Acta 1987, 70, 1981.
49. Murray, R. W.; Singh, M. Org. Synth. 1997, 74, 91.
50. Adam, W.; Zhao, C.; Saha-Moller, C. R.; Jakka, K. Oxidation of Organic Compounds by Dioxiranes; John Wiley & Sons: New York, 2009; p 35.
51. (a) Spartan 10, 1.2.0; Wavefunction, Inc.: Irvine, CA, 2008.
52. For a description of the improved calculation of 13C NMR chemical shifts in Spartan 10, see: Spartan '10 for Windows, Macintosh and Linux: Tutorial and User's Guide; Wavefunction, Inc.: Irvine, CA, 2011; pp 480-487.
53. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; 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.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision C.01; Gaussian, Inc.: Wallingford, CT, 2010.
54. See also: Foresman, J.B.; Frisch, A. Exploring Chemistry with Electronic Structure Methods, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1996.
55. Legault, C. Y. CYLview, 1.0b; Universite de Sherbrooke: Sherbrooke, Quebec, Canada, 2009. http://www.cylview.org.
56. Headley, J. V.; Peru, K. M.; Friesen, D. A.; Neu, T. J. Chromatogr. A 2001, 917, 159.
57. Prakash, G. K. S.; Rasul, G.; Liang, G.; Olah, G. A. J. Phys. Chem. 1996, 100, 15805.
58. Gabelica, V.; De Pauw, E. Mass Spectrom. Rev. 2005, 24, 566.
59. (a) Chandrasekhar, J.; Smith, S. F.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 154.
60. Jorgensen, W. L. Acc. Chem. Res. 1989, 22, 184.
61. Bartmess, J. E. In The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids; Rappoport, Z., Liebman, J. F., Eds.; John Wiley & Sons: West Essex, U.K., 2011; Vol. 2, Part 1, pp 115-143.
62. Buehler, E.; Brown, G. B. J. Org. Chem. 1967, 32, 265.
63. Paroline, H.; Morgan, J. P.; Greenberg, A., unpublished results.
64. Nakanishi, K.; Solomon, P. H. Infrared Absorption Spectroscopy, 2nd ed.; Holden-Day, Inc.: San Francisco, CA, 1977; pp 45-46.
65. Bailey, W. F.; Bobbitt, J. M.; Wiberg, K. B. J. Org. Chem. 2007, 72, 4504.
66. Canterbury, D. P.; Frontier, A. J.; Um, J. M.; Cheong, P. H. Y.; Goldfeld, D. A.; Huhn, R. A.; Houk, K. N. Org. Lett. 2008, 10, 4597.