Mechanistic insight into organic and catalytic reactions by joint studies using mass spectrometry and NMR spectroscopy

Mendeleev Communications

Volumn 20, Issue 3, 2010, Pages 125-131

  Belyakov, Pavel A ^a   Kadentsev, Valentine I ^a   Chizhov, Alexander O ^a   Kolotyrkina, Natal'Ya G ^a   Shashkov, Alexander S ^a   Ananikov, Valentine P ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77954196654     PISSN: 09599436     EISSN: 1364551X     Source Type: Journal    
DOI: 10.1016/j.mencom.2010.05.001     Document Type: Article

References (118)

1. A.G. Marshall, and C.L. Hendrickson Ann. Rev. Anal. Chem. 1 2008 579
2. K. Cottingham Anal. Chem. 77 2005 227A
3. J. H. Gross, Mass Spectrometry: A Textbook, Springer, Berlin, 2004.
4. L. Bluck, and D.A. Volmer Spectroscopy 23 2008 36
5. Early days of development: (a) A. L. Burlingame, C. H. L. Shackleton, I. Howe and O. S. Chizhov, Anal. Chem., 1978, 50, 346R
6. (b) A. L. Burlingame, T. A. Baillie, P. J. Derrick and O. S. Chizhov, Anal. Chem., 1980, 52, 214R
7. (c) A. A. Solov'ev, V. I. Kadentsev and O. S. Chizhov, Usp. Khim., 1979, 67, 1180
8. (Russ. Chem. Rev., 1979, 48, 631)
9. (d) O. S. Chizhov, V. I. Kadentsev, G. G. Palmbach, K. I. Burstein, S. A. Shevelev and A. A. Feinsilberg, Org. Mass Spectrom., 1978, 13, 611.
10. A. Bax, Two-dimensional NMR in Liquids, Delft University Press, Delft, 1982.
11. R. R. Ernst, G. Bodenhausen and A.Wokaun, Principles of NMR in One and Two Dimensions, Clarendon Press, Oxford, 1987.
12. G. E. Martin and A. S. Zektzer, Two-Dimensional NMR Methods for Establishing Molecular Connectivity, Wiley-VCH, 1988.
13. H. Friebolin, Basic One- and Two-Dimensional NMR Spectroscopy, Wiley-VCH, Weinheim, 2005.
14. On-Line LC-NMR and Related Techniques, ed. K. Albert, John Wiley & Sons, Ltd., New York, 2002.
15. M.V. Silva Elipe Anal. Chim. Acta 497 2003 1
16. A.P. Kumar, D. Jin, and Y.-I. Lee Appl. Spectrosc. Rev. 44 2009 267
17. J.M. Seco, E. Quiñoá, and R. Riguera Chem. Rev. 104 2004 17
18. T.J. Wenzel, and J.D. Wilcox Chirality 15 2003 256
19. R. Rothchild Enantiomer 5 2000 457
20. N.V. Orlov, and V.P. Ananikov Chem. Commun. 46 2010 3212
21. V.P. Ananikov, and I.P. Beletskaya Izv. Akad. Nauk, Ser. Khim. 2008 740 (Russ. Chem. Bull., Int. Ed., 2008, 57, 754)
22. C.R. Yonker, and J.C. Linehan Prog. Nucl. Magn. Reson. Spectrosc. 47 2005 95
23. D. Stock, O. Perisic, and J. Löwe Prog. Biophys. Mol. Biol. 88 2005 311
24. N.E. Chayen Prog. Biophys. Mol. Biol. 88 2005 329
25. M.N. Eberlin Eur. J. Mass Spectrom. 13 2007 19
26. L.S. Santos Eur. J. Org. Chem. 2008 235
27. V.B. Di Marco, and G.G. Bombi Mass Spectrom. Rev. 25 2006 347
28. P. Kebarle, and U.H. Verkerk Mass Spectrom. Rev. 28 2009 898
29. (a) V. I. Kadentsev, A. O. Chizhov, O. S. Chizhov, O. N. Krupinova, V. M. Rzheznikov and L. E. Golubovskaya, Eur. J. Mass. Spectrom., 2006, 12, 75
30. (b) V. I. Kadentsev, A. O. Chizhov, O. S. Chizhov, N. G. Kolotyrkina, A. A. Kutin, I. D. Nesterov, N. D. Chuvylkin, V. M. Rzheznikov and L. E. Golubovskaya, Eur. J. Mass. Spectrom., 2007, 13, 207
31. (c) V. I. Kadentsev, A. O. Chizhov, O. S. Chizhov, N. G. Kolotyrkina, A. A. Kutin, V. M. Rzheznikov and L. E. Golubovskaya, Izv. Akad. Nauk, Ser. Khim., 2008, 92.
32. (Russ. Chem. Bull., Int. Ed., 2008, 57, 95).
33. H. Kovacs, D. Moskau, and M. Spraul Prog. Nucl. Magn. Reson. Spectrosc. 46 2005 131
34. G.E. Martin Ann. Rep. NMR Spectrosc. 56 2005 1
35. T. Fujiwara, and A. Ramamoorthy Ann. Rep. NMR Spectrosc. 58 2006 155
36. E.E. Kwan, and S.G. Huang Eur. J. Org. Chem. 2008 2671
37. Y. Maguire, I.L. Chuang, S. Zhang, and N. Gershenfeld Proc. Natl. Acad. Sci. USA 104 2007 9198
38. A.P.M. Kentgens, J. Bart, P.J.M. van Bentum, A. Brinkmann, E.R.H. van Eck, J.G.E. Gardeniers, J.W.G. Janssen, P. Knijn, S. Vasa, and M.H.W. Verkuijlen J. Chem. Phys. 128 2008 052202
39. D.L. Olson, T.L. Peck, A.G. Webb, R.L. Magin, and J.V. Sweedler Science 270 1995 1967
40. G. Bodenhausen, and R. Freeman J. Magn. Reson. 28 1977 471
41. A.A. Maudsley, and R.R. Ernst Chem. Phys. Lett. 50 1977 368
42. G. Bodenhausen, and D.J. Ruben Chem. Phys. Lett. 69 1980 185
43. A. Bax, R.H. Griffey, and B.L. Hawkins J. Magn. Reson. 55 1983 301
44. J. Skonieczny, L. Latos-Grazyński, and L. Szterenberg Chem. Eur. J. 14 2008 4861
45. V. Gallo, M. Latronico, P. Mastrorilli, C.F. Nobile, F. Polini, N. Re, and U. Englert Inorg. Chem. 47 2008 4785
46. M.M. Dell'Anna, P. Mastrorilli, C.F. Nobile, B. Calmuschi-Cula, U. Englert, and M. Peruzzini Dalton Trans. 2008 6005
47. V. Ananikov, S.A. Mitchenko, I.P. Beletskaya, S.E. Nefedov, and I.L. Eremenko Inorg. Chem. Commun. 1 1998 411
48. V.P. Ananikov, S.A. Mitchenko, and I.P. Beletskaya Zh. Org. Khim. 38 2002 672 (Russ. J. Org. Chem., 2002, 38, 636)
49. V.P. Ananikov, S.A. Mitchenko, and I.P. Beletskaya Dokl. Akad. Nauk 363 1998 343
50. [Dokl. Chem. (Engl. Transl.), 1998, 363, 225]
51. (a) V. P. Ananikov, D. A. Malyshev, I. P. Beletskaya, G. G. Aleksandrov and I. L. Eremenko, Adv. Synth. Catal., 2005, 347, 1993
52. (b) P. Ribière, K. Bravo-Altamirano, M. I. Antczak, J. D. Hawkins and J.-L.Montchamp, J. Org. Chem., 2005, 70, 4064
53. (c) M. M. Heravi, K. Bakhtiari, H. A. Oskooie and S. Taheri, J. Mol. Cat. A-Chem., 2007, 263, 279
54. (d) G. Liu, Q. L. Du, J. J. Xie, K. L. Zhang and X. C. Tao, Chin. J. Catal., 2006, 27, 1051
55. (e) D. Zim and A. L. Monteiro, Tetrahedron Lett., 2002, 43, 2009.
56. Y. Ruff, and J.-M. Lehn Biopolymers 89 2007 486
57. B. Champin, V. Sartor, and J.-P. Sauvage New J. Chem. 32 2008 1048
58. C. Schmuck, T. Rehm, F. Gröhn, K. Klein, and F. Reinhold J. Am. Chem. Soc. 128 2006 1430
59. P.J. Chmielewski, J. Macio ek, and L. Szterenberg Eur. J. Org. Chem. 2009 3930
60. A. Westcott, J. Fisher, L.P. Harding, P. Rizkallah, and M.J. Hardie J. Am. Chem. Soc. 130 2008 2950
61. H. Maeda, Y. Haketa, and T. Nakanishi J. Am. Chem. Soc. 129 2007 13661
62. A. Gasnier, J.-M. Barbe, C. Bucher, F. Denat, J.-C. Moutet, E. Saint-Aman, P. Terech, and G. Royal Inorg. Chem. 47 2008 1862
63. M. Chas, V. Blanco, C. Peinador, and J.M. Quintela Org. Lett. 9 2007 675
64. D. Neuhaus and M. P. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis, Wiley-VCH, Weinheim, 2000.
65. T. Brand, E.J. Cabrita, and S. Berger Prog. Nucl. Magn. Reson. Spectrosc. 46 2005 159
66. A. Lohr, M. Grüne, and F. Würthner Chem. Eur. J. 15 2009 3691
67. M. Bretz, A. Knecht, S. Göckler, and H.-U. Humpf Mol. Nutr. Food Res. 49 2005 309
68. A. Grube, and M. Köck Angew. Chem. Int. Ed. 46 2007 2320
69. C. Mehner, D. Müller, S. Kehraus, S. Hautmann, M. Gütschow, and G.M. König ChemBioChem 9 2008 2692
70. K.V. Rao, M. Na, J.C. Cook, J. Peng, R. Matsumoto, and M.T. Hamann J. Nat. Prod. 71 2008 772
71. M. El-Naggar, A.M. Piggott, and R.J. Capon Org. Lett. 10 2008 4247
72. P.J. Chmielewski Inorg. Chem. 48 2009 432
73. S. Bonnet, J.-P. Collin, and J.-P. Sauvage Inorg. Chem. 46 2007 10520
74. S.P. Reade, D. Nama, M.F. Mahon, P.S. Pregosin, and M.K. Whittlesey Organometallics 26 2007 3484
75. A. Marquis, V. Smith, J. Harrowfield, J.-M. Lehn, H. Herschbach, R. Sanvito, E. Leize-Wagner, and A.V. Dorsselaer Chem. Eur. J. 12 2006 5632
76. P.L. Métayer, P. Schaeffer, P. Adam, P. Albrecht, S. Roussé, and P. Duringer Org. Geochem. 39 2008 658
77. L.H. Pham, J. Vater, W. Rotard, and C. Mügge Magn. Reson. Chem. 43 2005 710
78. A.S. Shashkov, G.M. Lipkind, Y.A. Knirel, and N.K. Kochetkov Magn. Reson. Chem. 26 1988 735
79. A.S. Shashkov, G.M. Lipkind, and N.K. Kochetkov Carbohydr. Res. 147 1986 175
80. G.M. Lipkind, A.S. Shashkov, S.S. Mamyan, and N.K. Kochetkov Carbohydr. Res. 181 1988 1
81. N.K. Kochetkov, O.S. Chizhov, and A.S. Shashkov Carbohydr. Res. 133 1984 173
82. N.K. Kochetkov, O.S. Chizhov, and N.V. Molodtsov Tetrahedron 24 1968 5587
83. N.K. Kochetkov, O.S. Chizhov, and A.F. Sviridov Carbohydr. Res. 14 1970 277
84. O.S. Chizhov, A.B. Foster, M. Jarman, and J.H. Westwood Carbohydr. Res. 22 1972 37
85. (a) N. A. Kocharova, A. N. Kondakova, E. Vinogradov, O. G. Ovchinnikova, B. Lindner, A. S. Shashkov, A. Rozalski and Y. A. Knirel, Chem. Eur. J., 2008, 14, 6184
86. (b) A. N. Kondakova, N. Ho, O. V. Bystrova, A. S. Shashkov, B. Lindner, C. Creuzenet and Y. A. Knirel, Carbohydr. Res., 2008, 343, 1383
87. (c) A. V. Perepelov, B. Liu, S. D. Shevelev, S. N. Senchenkova, A. S. Shashkov, L. Feng, Y. A. Knirel and L.Wang, Carbohydr. Res., 2010, 345, 825
88. (d) A. N. Kondakova, B. Linder, R. Fudala, S. N. Senchenkova, H. Moll, A. S. Shashkov, W. Kaca, U. Zähringer and Y. A. Knirel, Biokhimiya, 2004, 69, 1271.
89. [Biochemistry (Moscow), 2004, 69, 1034]
90. L.S. Santos, and J.O. Metzger Angew. Chem. Int. Ed. 45 2006 977
91. R. Subramanian, W.P. Kelley, P.D. Floyd, Z.J. Tan, A.G. Webb, and J.V. Sweedler Anal. Chem. 71 1999 5335
92. E.E. McDonnell, S. Han, C. Hilty, K.L. Pierce, and A. Pines Anal. Chem. 77 2005 8109
93. H. Wensink, F. Benito-Lopez, D.C. Hermes, W. Verboom, H.J.G.E. Gardeniers, D.N. Reinhoudt, and A. van den Berg Lab Chip 5 2005 280
94. S. Ahola, F. Casanova, J. Perlo, K. Münnemann, B. Blümich, and S. Stapf Lab Chip 6 2006 90
95. I.V. Koptyug, L.Y. Ilyina, A.V. Matveev, R.Z. Sagdeev, V.N. Parmon, and S.A. Altobelli Catalysis Today 69 2001 385
96. I.V. Koptyug, A.A. Lysova, K.V. Kovtunov, V.V. Zhivonitko, A.V. Khomichev, and R.Z. Sagdeev Usp. Khim. 76 2007 628
97. (Russ. Chem. Rev., 2007, 76, 583)
98. A.A. Lysova, J.A. Bergwerff, L. Espinosa-Alonso, B.M. Weckhuysen, and I.V. Koptyug Appl. Cat. A - Gen. 374 2010 126
99. W. Koch and M. C. Holthausen, A Chemist's Guide to Density Functional Theory, Wiley-VCH, Weinheim, 2002.
100. Computational Modeling for Homogeneous and Enzymatic Catalysis: A Knowledge-Base for Designing Efficient Catalysts, eds. K. Morokuma and D. G. Musaev, Wiley-VCH, Weinheim, 2008.
101. Modelling NMR Chemical Shifts, eds. J. C. Facelli and A. C. de Dios, ACS Symposium series 732, American Chemical Society, Washington, DC, 1999.
102. T. Vreven, and K. Morokuma Ann. Rep. Comput. Chem. 2 2006 35
103. K. Morokuma Bull. Chem. Soc. Jpn. 80 2007 2247
104. V.P. Ananikov, D.G. Musaev, and K. Morokuma Eur. J. Inorg. Chem. 2007 5390
105. V.N. Khabashesku, K.N. Kudin, J. Tamás, S.E. Boganov, J.L. Margrave, and O.M. Nefedov J. Am. Chem. Soc. 120 1998 5005
106. (a) X.-Y. Yu, X. Xu and Z. Chen, Int. J. Mass Spectrom., 2008, 269, 138
107. (b) J. C. Choe, Int. J. Mass Spectrom., 2008, 278, 50
108. (c) P. Skurski, J. Simons, X.-B. Wang and L.-S. Wang, J. Am. Chem. Soc., 2000, 122, 4499
109. (d) M. J. Rusyniak, Y. M. Ibrahim, D. L. Wright, S. N. Khanna and M. S. El-Shall, J. Am. Chem. Soc., 2003, 125, 12001
110. (e) Y. Guo, S. Cao, D. Wei, X. Zong, X. Yuan, M. Tang and Y. Zhao, J. Mass. Spectrom., 2009, 44, 1188
111. (f) B. Amekraz, J. Tortajada, J.-P. Morizur, A. I. González, O. Mó, M. Yáñez, I. Leito, P.-C. Maria and J.-F. Gal, New J. Chem., 1996, 20, 1011
112. (g) N. D. Chuvylkin, I. D. Nesterov and V. I. Kadentsev, Izv. Akad. Nauk, Ser. Khim., 2008, 246.
113. (Russ. Chem. Bull., Int. Ed., 2008, 57, 253).
114. M. Alcamí, O. Mó, and M. Yáñez Mass Spectrom. Rev. 20 2001 195
115. G.W. Amarante, M. Benassi, H.M.S. Milagre, A.A.C. Braga, F. Maseras, M.N. Eberlin, and F. Coelho Chem. Eur. J. 15 2009 12460
116. I.S. Ufimtsev, and T.J. Martínez J. Chem. Theory Comput. 4 2008 222
117. I.S. Ufimtsev, and T.J. Martínez J. Chem. Theory Comput. 5 2009 1004
118. I.S. Ufimtsev, and T.J. Martínez J. Chem. Theory Comput. 5 2009 2619