The role of mass spectrometric methods in ionic reaction mechanistic studies

International Journal of Mass Spectrometry - Tập 200 - Trang 27-42 - 2000
Nico M.M Nibbering1
1Institute of Mass Spectrometry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam The Netherlands

Tài liệu tham khảo

Beynon, 1960 Mass Spectrometry of Organic Ions, F.W. McLafferty (Ed.), Academic, New York, 1963. Budzikiewicz, 1967 K.R. Jennings, J. Chem. Phys. 43 (1965) 4176; K.R. Jennings in R. Bonnett, J.G. Davis (Eds.), Some Newer Physical Methods in Structural Chemistry, United Trade, London, 1967, p. 105. McLafferty, 1956, Anal. Chem., 28, 306, 10.1021/ac60111a005 Nibbering, 1965, Rec. Trav. Chim., 84, 481, 10.1002/recl.19650840412 Molenaar-Langeveld, 1974, Org. Mass Spectrom., 9, 257, 10.1002/oms.1210090212 Fairweather, 1969, Org. Mass Spectrom., 2, 755, 10.1002/oms.1210020710 Kingston, 1974, Chem. Rev., 74, 215, 10.1021/cr60288a004 Nibbering, 1968, Tetrahedron, 24, 1427, 10.1016/0040-4020(68)88094-9 Woodward, 1969, Angew. Chem., 81, 797, 10.1002/ange.19690812102 Roberts, 1965 Jennings, 1968, Int. J. Mass Spectrom. Ion Phys., 1, 227, 10.1016/0020-7381(68)85002-8 McLafferty, 1969, J. Am. Chem. Soc., 91, 1866, 10.1021/ja01035a057 K.H. Maurer, C. Brunnée, G. Kappus, K. Habfast, U. Schröder, P. Schulze, 19th Annual Conference on Mass Spectrometry, Atlanta, GA, 1971, paper K-9. McLafferty, 1973, J. Am. Chem. Soc., 95, 2120, 10.1021/ja00788a007 McLafferty, 1973, J. Am. Chem. Soc., 95, 3886, 10.1021/ja00793a011 Tandem Mass Spectrometry, F.W. McLafferty (Ed.), Wiley, New York, 1983. Levsen, 1983, Mass Spectrom. Rev., 2, 77, 10.1002/mas.1280020104 Nibbering, 1974, J. Am. Chem. Soc., 96, 5668, 10.1021/ja00824a108 Shapiro, 1969, Org. Mass Spectrom., 2, 771, 10.1002/oms.1210020802 Lowry, 1981 Hehre, 1972, J. Am. Chem. Soc., 94, 5919, 10.1021/ja00771a078 Maas, 1989, Org. Mass Spectrom., 24, 546, 10.1002/oms.1210240807 Nibbering, 1974, Org. Mass Spectrom., 9, 1059, 10.1002/oms.1210091015 Kerkhoff, 1973, Org. Mass Spectrom., 7, 37, 10.1002/oms.1210070107 Hipple, 1946, Phys. Rev., 69, 347, 10.1103/PhysRev.69.347 Beynon, 1965, Z. Naturforsch. Teil A, 20, 180, 10.1515/zna-1965-0203 Beynon, 1967, Z. Naturforsch. Teil A, 22, 334, 10.1515/zna-1967-0307 Cooks, 1973 Holmes, 1985, Org. Mass Spectrom., 20, 169, 10.1002/oms.1210200302 Rumpf, 1988, Int. J. Mass Spectrom. Ion Processes, 82, 239, 10.1016/0168-1176(88)80018-1 Schoemaker, 1975, J. Am. Chem. Soc., 97, 4415, 10.1021/ja00848a057 Nibbering, 1979, Philos. Trans. R. Soc. London, Ser. A, 293, 103, 10.1098/rsta.1979.0082 Molenaar-Langeveld, 1978, Org. Mass Spectrom., 13, 172, 10.1002/oms.1210130311 G. Bouchoux, Mass Spectrom. Rev. 7 (1988) 1; 7 (1988) 203. Burgers, 1984, Org. Mass Spectrom., 19, 442, 10.1002/oms.1210190908 Burgers, 1983, Chem. Phys. Lett., 102, 1, 10.1016/0009-2614(83)80645-9 Terlouw, 1985, Int. J. Mass Spectrom. Ion Processes, 66, 239, 10.1016/0168-1176(85)83013-5 Terlouw, 1989, Adv. Mass Spectrom., 11B, 984 Terlouw, 1987, Angew. Chem. Int. Ed. Engl., 26, 805, 10.1002/anie.198708053 J.S. Splitter, in Applications of Mass Spectrometry to Organic Stereochemistry, J.S. Splitter, F. Turecek (Eds.), VCH, Weinheim, 1994, Chap. 3. Fell, 1998, Can. J. Chem., 76, 335 Schulze, 1971, Int. J. Mass Spectrom. Ion Phys., 6, 131, 10.1016/0020-7381(71)83011-5 Derrick, 1972, J. Am. Chem. Soc., 94, 6794, 10.1021/ja00774a037 Beckey, 1961, Z. Naturforsch. Teil A, 16, 505, 10.1515/zna-1961-0509 Nibbering, 1984, Mass Spectrom. Rev., 3, 445, 10.1002/mas.1280030402 Nibbering, 1991, 333 Nibbering, 1999, Vol. 1, 539 Levsen, 1978 Willhalm, 1968, Org. Mass Spectrom., 1, 627, 10.1002/oms.1210010504 Zwinselman, 1981, Int. J. Mass Spectrom. Ion Phys., 38, 163, 10.1016/0020-7381(81)80065-4 Zappey, 1991, Org. Mass Spectrom., 26, 241, 10.1002/oms.1210260411 Russell, 1979, J. Am. Chem. Soc., 101, 2086, 10.1021/ja00502a025 Sommer, 1951, Phys. Rev., 82, 697, 10.1103/PhysRev.82.697 Baldeschwieler, 1968, Science, 159, 263, 10.1126/science.159.3812.263 Goode, 1970, Nature, 227, 1093, 10.1038/2271093a0 Baldeschwieler, 1971, Acc. Chem. Res., 4, 114, 10.1021/ar50039a006 C.J. Drewery, G.C. Goode, K.R. Jennings, in M.T.P. International Review of Science (Physical Chemistry), A. Maccoll (Ed.), Butterworths, London, 1972, Vol. 5, p. 183. Lehman, 1976 McIver, 1970, Rev. Sci. Instrum., 41, 555, 10.1063/1.1684576 Anders, 1966, J. Chem. Phys., 45, 1062, 10.1063/1.1727658 Beauchamp, 1968, J. Chem. Phys., 48, 1783, 10.1063/1.1668912 N.M.M. Nibbering, in Kinetics of Ion–Molecule Reactions, NATO Advanced Study Institutes Series B: Physics, P. Ausloos (Ed.), Plenum, New York, 1979, Vol. 40, p. 165. Nibbering, 1981, Recl. Trav. Chim. Pays-Bas, 100, 297, 10.1002/recl.19811000902 Nibbering, 1973, Tetrahedron, 29, 385, 10.1016/S0040-4020(01)93306-X Theissling, 1971, Adv. Mass Spectrom., 5, 642 van der Greef, 1978, Adv. Mass Spectrom., 7A, 153 Theissling, 1978, Adv. Mass Spectrom., 7B, 1287 Russell, 1979, Org. Mass Spectrom., 14, 474, 10.1002/oms.1210140904 van Velzen, 1982, J. Am. Chem. Soc., 104, 1208, 10.1021/ja00369a009 Longevialle, 1980, J. Chem. Soc. Chem. Commun., 823, 10.1039/c39800000823 Morton, 1980, J. Am. Chem. Soc., 102, 1596, 10.1021/ja00525a022 Morton, 1982, Tetrahedron, 38, 3195, 10.1016/0040-4020(82)80101-4 Longevialle, 1992, Mass Spectrom. Rev., 11, 157, 10.1002/mas.1280110302 Heck, 1993, Org. Mass Spectrom., 28, 235, 10.1002/oms.1210280316 Kohler, 1999, J. Phys. Chem. A, 103, 2302, 10.1021/jp983654r Chantry, 1969, J. Chem. Phys., 51, 3369, 10.1063/1.1672521 Jennings, 1979, Philos. Trans. R. Soc. London, Ser. A, 293, 125, 10.1098/rsta.1979.0084 K.R. Jennings in Mass Spectrometry, R.A.W. Johnstone (Ed.), The Chemical Society, London, 1977, Vol. 4, Chap. 9, p. 203. Dawson, 1977, Org. Mass Spectrom., 12, 330, 10.1002/oms.1210120515 Dawson, 1979, Int. J. Mass Spectrom. Ion Phys., 30, 189, 10.1016/0020-7381(79)80095-9 Lee, 1992, Chem. Rev., 92, 1611, 10.1021/cr00015a007 Born, 1997, Mass Spectrom. Rev., 16, 181, 10.1002/(SICI)1098-2787(1997)16:4<181::AID-MAS2>3.0.CO;2-D Dawson, 1980, Int. J. Mass Spectrom. Ion Phys., 33, 3, 10.1016/0020-7381(80)80030-1 Bowie, 1990, Mass Spectrom. Rev., 9, 349, 10.1002/mas.1280090305 McIver, 1970, Rev. Sci. Instrum., 41, 555, 10.1063/1.1684576 M.B. Comisarow, A.G. Marshall, Chem. Phys. Lett. 25 (1974) 282; see also Can. J. Chem. 52 (1974) 1997. Dawson, 1982, Vol. 31, 331 A.J. Noest, C.W.F. Kort, Comput. Chem. 6 (1982) 111; 6 (1982) 115; 7 (1983) 81. Nibbering, 1993, Rapid Commun. Mass Spectrom., 7, 747, 10.1002/rcm.1290070813 A.G. Marshall, C.L. Hendrickson, G.S. Jackson, Mass Spectrom. Rev. 17 (1998) 1, and references cited therein. Gross, 1984, Science, 226, 261, 10.1126/science.6385250 Comisarow, 1980, Adv. Mass Spectrom., 8, 1698 Nibbering, 1998, Adv. Mass Spectrom., 14, 43 Nibbering, 1990, Acc. Chem. Res., 23, 279, 10.1021/ar00177a003 Nibbering, 1988, Adv. Phys. Org. Chem., 24, 1, 10.1016/S0065-3160(08)60157-4 Nibbering, 1986, Recl. Trav. Chim. Pays-Bas, 105, 245, 10.1002/recl.19861050903 Kleingeld, 1982, Org. Mass Spectrom., 17, 136, 10.1002/oms.1210170307 Dang, 1992, Int. J. Mass Spectrom. Ion Processes, 117, 65, 10.1016/0168-1176(92)80086-G Bass, 1983, J. Am. Chem. Soc., 105, 7024, 10.1021/ja00362a003 Raghavachari, 1984, J. Am. Chem. Soc., 106, 3124, 10.1021/ja00323a009 Sheldon, 1986, J. Chem. Soc. Perkin Trans., 2, 941, 10.1039/p29860000941 Bouchoux, 1997, Rapid Commun. Mass Spectrom., 11, 1799, 10.1002/(SICI)1097-0231(19971030)11:16<1799::AID-RCM61>3.0.CO;2-4 Graul, 1987, Int. J. Mass Spectrom. Ion Processes, 81, 183, 10.1016/0168-1176(87)80012-5 Kleingeld, 1983, Int. J. Mass Spectrom. Ion Phys., 49, 311, 10.1016/0020-7381(83)85081-5 R.R. Squires, in Structure/Reactivity and Thermochemistry of Ions, P. Ausloos, S.G. Lias (Eds.), NATO Advanced Study Institutes Series C: Mathematical and Physical Sciences Vol. 193, Reidel, Dordrecht, 1987, p. 373. Paulson, 1982, Bull. Am. Phys. Soc., 27, 108 Miller, 1985, Bull. Am. Phys. Soc., 30, 880 R.R. Squires, in Ionic Processes in the Gas Phase, M.A. Almoster Ferreira (Ed.), NATO Advanced Study Institutes Series C: Mathematical and Physical Sciences Vol. 118, Reidel, Dordrecht, 1984, p. 337. Cremer, 1986, J. Phys. Chem., 90, 33, 10.1021/j100273a010 Chalasinski, 1987, J. Chem. Phys., 97, 2965, 10.1063/1.453032 van der Wel, 1988, Recl. Trav. Chim. Pays-Bas, 107, 491, 10.1002/recl.19881070704 Kleingeld, 1983, J. Am. Chem. Soc., 105, 2474, 10.1021/ja00346a061 Coe, 1985, J. Chem. Phys., 83, 3169, 10.1063/1.449223 Kalcher, 1984, Can. J. Phys., 62, 1323, 10.1139/p84-179 Cardy, 1986, Chem. Phys. Lett., 131, 507, 10.1016/0009-2614(86)80573-5 van der Wel, 1988, Recl. Trav. Chim. Pays-Bas, 107, 491, 10.1002/recl.19881070704 Ingemann, 1982, J. Am. Chem. Soc., 104, 6520, 10.1021/ja00388a007 N.M.M. Nibbering, S. Ingemann, L.J. de Koning in The Structure, Energetics and Dynamics of Organic Ions, T. Baer, C.-Y. Ng, I. Powis (Eds.) Wiley, Chichester, 1996, Chap. 7. R.L. Smith, P.K. Chou, H.I. Kenttämaa, in The Structure, Energetics and Dynamics of Organic Ions, T. Baer, C.-Y. Ng, I. Powis (Eds.), Wiley, Chichester, 1996, Chap. 5. Kenttämaa, 1994, Org. Mass Spectrom., 29, 1, 10.1002/oms.1210290102 Stirk, 1992, Chem. Rev., 92, 1649, 10.1021/cr00015a008 Troude, 1997, J. Am. Chem. Soc., 119, 9287, 10.1021/ja9707365 Audier, 1996, J. Phys. Chem., 100, 18380, 10.1021/jp960114q Diefenbach, 1999, J. Am. Chem. Soc., 121, 10614, 10.1021/ja992642w Brönstrup, 1999, Organometallics, 18, 1939, 10.1021/om981015x Pavlov, 1997, J. Phys. Chem. A, 101, 1567, 10.1021/jp962966w Heinemann, 1996, Inorg. Chem., 35, 2463, 10.1021/ic951322k Stöckigt, 1995, Liebigs Ann, 429, 10.1002/jlac.199519950253 Ryan, 1994, J. Am. Chem. Soc., 116, 9565, 10.1021/ja00100a021 T.H. Morton, in Techniques for the Study of Ion-Molecule Reactions, J.M. Farrar, W.H. Saunders Jr. (Eds.), Wiley-Interscience, New York, 1988, Chap. III. D.J. McAdoo, T.H. Morton, Acc. Chem. Res. 26 (1993) 295, and references cited therein. van der Hart, 1992, Adv. Mass Spectrom., 12, 617, 10.1016/B978-0-444-88871-6.50032-5 R.C. Dunbar, in Gas Phase Ion Chemistry, M.T. Bowers (Ed.), Academic, New York, 1984, Vol. 3, Chap. 20. Cacace, 1988, Acc. Chem. Res., 21, 215, 10.1021/ar00150a001 Speranza, 1992, Mass Spectrom. Rev., 11, 73, 10.1002/mas.1280110203 DePuy, 1981, Acc. Chem. Res., 14, 146, 10.1021/ar00065a003 DePuy, 1982, Science, 218, 955, 10.1126/science.218.4576.955