Efficient and selective gas-phase monomethylation versus N-H bond activation of ammonia by "bare" Zn(CH3)+: Atomic zinc as a leaving group in an SN2 reaction

Angewandte Chemie - International Edition

Volumn 50, Issue 23, 2011, Pages 5387-5391

  Kretschmer, Robert ^a   Schlangen, Maria ^a   Schwarz, Helmut ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

amines; ammonia; C N bond formation; DFT calculations; gas phase reactions

Indexed keywords

C-H BOND; C-N BOND FORMATION; CARBON AND NITROGEN; DFT CALCULATION; GAS-PHASE REACTIONS; GASPHASE; LEAVING GROUPS; MONOMETHYLATION; N-H BOND ACTIVATION;

AMMONIA; METHANE; NITROGEN; PHASE INTERFACES;

ZINC;

AMINE; AMMONIA; CARBON; HYDROGEN; ZINC;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; METHYLATION; THERMODYNAMICS;

AMINES; AMMONIA; CARBON; CATALYSIS; HYDROGEN; METHYLATION; MODELS, CHEMICAL; MOLECULAR STRUCTURE; THERMODYNAMICS; ZINC;

EID: 79957534565     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201100096     Document Type: Article

References (121)

1. T. Henkel, R. M. Brunne, H. Müller, F. Reichel, Angew. Chem. 1999, 111, 688-691
2. Angew. Chem. Int. Ed. 1999, 38, 643-647
3. Comprehensive Natural Products Chemistry, Vol. 4 (Eds.:, D. H. R. Barton, K. Nakanishi, O. Meth-Cohn,), Elsevier, Oxford, 1999
4. R. Hili, A. K. Yudin, Nat. Chem. Biol. 2006, 2, 284-287
5. J. P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651-2710
6. G. Evano, N. Blanchard, M. Toumi, Chem. Rev. 2008, 108, 3054-3131
7. Handbook of Heterogeneous Catalysis, 2 nd ed (Eds.:, G. Ertl, H. Knözinger, F. Schüth, J. Weitkamp,), Wiley-VCH, Weinheim, 2008.
8. J. P. Wolfe, S. Wagaw, J. F. Marcoux, S. L. Buchwald, Acc. Chem. Res. 1998, 31, 805-818
9. J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177
10. Angew. Chem. Int. Ed. 1998, 37, 2046-2067
11. M. Kienle, S. R. Dubbaka, K. Brade, P. Knochel, Eur. J. Org. Chem. 2007, 4166-4176
12. F. Collet, R. H. Dodd, P. Dauban, Chem. Commun. 2009, 5061-5074
13. J. I. van der Vlugt, Chem. Soc. Rev. 2010, 39, 2302-2322
14. J. L. Klinkenberg, J. F. Hartwig, Angew. Chem. 2011, 123, 88-98
15. Angew. Chem. Int. Ed. 2011, 50, 86-95.
16. S. V. Gredig, R. A. Koeppel, A. Baiker, Appl. Catal. A 1997, 162, 249-260.
17. S. V. Gredig, R. A. Koeppel, A. Baiker, J. Chem. Soc. Chem. Commun. 1995, 73-74
18. S. V. Gredig, R. A. Koeppel, A. Baiker, Catal. Today 1996, 29, 339-342
19. D. R. Corbin, S. Schwarz, G. C. Sonnichsen, Catal. Today 1997, 37, 71-102
20. M. Pérez-Mendoza, M. Domingo-Garcia, F. J. Lopez-Garzon, Appl. Catal. A 2002, 224, 239-253
21. N. F. P. Ribeiro, C. A. Henriques, M. Schmal, Catal. Lett. 2005, 104, 111-119.
22. C. Gründling, V. A. Veefkind, G. EderMirth, J. A. Lercher, Stud. Surf. Sci. Catal. 1997, 105, 591-598
23. V. A. Veefkind, J. A. Lercher, Appl. Catal. A 1999, 181, 245-255.
24. S. M. Auer, S. V. Gredig, R. A. Koppel, A. Baiker, J. Mol. Catal. A 1999, 141, 193-203
25. G. Carja, R. Nakamura, H. Niiyama, Appl. Catal. A 2002, 236, 91-102.
26. F. Ullmann, Ber. Dtsch. Chem. Ges. 1903, 36, 2382-2384
27. F. Ullmann, E. Illgen, Ber. Dtsch. Chem. Ges. 1914, 47, 380-383
28. S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558-5607
29. Angew. Chem. Int. Ed. 2003, 42, 5400-5449
30. F. Monnier, M. Taillefer, Angew. Chem. 2008, 120, 3140-3143
31. Angew. Chem. Int. Ed. 2008, 47, 3096-3099
32. F. Monnier, M. Taillefer, Angew. Chem. 2009, 121, 7088-7105
33. Angew. Chem. Int. Ed. 2009, 48, 6954-6971.
34. V. Merz, K. Gasiorowski, Ber. Dtsch. Chem. Ges. 1884, 17, 623-640.
35. K. Eller, H. Schwarz, Chem. Rev. 1991, 91, 1121-1177
36. D. K. Böhme, H. Schwarz, Angew. Chem. 2005, 117, 2388-2406
37. Angew. Chem. Int. Ed. 2005, 44, 2336-2354
38. J. Roithová, D. Schröder, Chem. Rev. 2010, 110, 1170-1211
39. J. M. Garver, Y. R. Fang, N. Eyet, S. M. Villano, V. M. Bierbaum, K. C. Westaway, J. Am. Chem. Soc. 2010, 132, 3808-3814
40. D. Agrawal, D. Schröder, Organometallics 2011, 30, 32-35
41. H. Schwarz, Angew. Chem. 2011, DOI:; Angew. Chem. Int. Ed. 2011, DOI:.
42. M. Aschi, M. Brönstrup, M. Diefenbach, J. N. Harvey, D. Schröder, H. Schwarz, Angew. Chem. 1998, 110, 858-861
43. Angew. Chem. Int. Ed. 1998, 37, 829-832
44. M. Diefenbach, M. Brönstrup, M. Aschi, D. Schröder, H. Schwarz, J. Am. Chem. Soc. 1999, 121, 10614-10625
45. K. Koszinowski, D. Schröder, H. Schwarz, Organometallics 2003, 22, 3809-3819
46. H. Schwarz, Angew. Chem. 2003, 115, 4580-4593
47. Angew. Chem. Int. Ed. 2003, 42, 4442-4454.
48. K. Koszinowski, D. Schröder, H. Schwarz, J. Am. Chem. Soc. 2003, 125, 3676-3677
49. K. Koszinowski, D. Schröder, H. Schwarz, Angew. Chem. 2004, 116, 124-127
50. Angew. Chem. Int. Ed. 2004, 43, 121-124
51. K. Koszinowski, D. Schröder, H. Schwarz, Organometallics 2004, 23, 1132-1139.
52. R. Georgiadis, P. B. Armentrout, J. Am. Chem. Soc. 1986, 108, 2119-2126.
53. T. F. Magnera, D. E. David, J. Michl, J. Am. Chem. Soc. 1989, 111, 4100-4101.
54. X. Zhang, H. Schwarz, Theor. Chem. Acc. 2011, DOI:.
55. D. E. Clemmer, N. Aristov, P. B. Armentrout, J. Phys. Chem. 1993, 97, 544-552
56. Organometallic Ion chemistry (Ed.:, B. S. Freiser,), Kluwer, Dordrecht Holland, 1996
57. D. E. Clemmer, L. S. Sunderlin, P. B. Armentrout, J. Phys. Chem. 1990, 94, 208-217
58. D. E. Clemmer, L. S. Sunderlin, P. B. Armentrout, J. Phys. Chem. 1990, 94, 3008-3015
59. D. E. Clemmer, P. B. Armentrout, J. Phys. Chem. 1991, 95, 3084-3090.
60. For the thermal N-H bond activation of ammonia, see
61. G. K. Koyanagi, V. Kapishon, D. K. Bohme, Z. Xhang, H. Schwarz, Eur. J. Inorg. Chem. 2010, 1516-1521
62. R. Kretschmer, X. Zhang, M. Schlangen, H. Schwarz, Chem. Eur. J. 2011, 17, 3886-3892, and references therein.
63. +.
64. 4 system as a reference:, D. Schröder, H. Schwarz, Can. J. Chem. 2005, 83, 1936-1940, and references therein
65. collision-rate calculations were performed by using the ADO method:, T. Su, M. T. Bowers, J. Chem. Phys. 1973, 58, 3027-3037.
66. [21c]
67. R. H. Nobes, L. Radom, Chem. Phys. 1983, 74, 163-169.
68. R. Rüede, H. Troxler, C. Beglinger, M. Jungen, Chem. Phys. Lett. 1993, 203, 477-481
69. J. Berkowitz, G. B. Ellison, D. Gutman, J. Phys. Chem. 1994, 98, 2744-2765
70. J. Sugar, A. Musgrove, J. Phys. Chem. Ref. Data 1995, 24, 1803-1872.
71. N2 reactions, we have applied the following strategy: The reaction pathways were optimized at the UB3LYP/def2-QZVP level, and for the so-obtained geometries of selected species (intermediates, transition states) single-point calculations were performed at the UCCSD(T)/def2-QZVP level; the energetic data given in Figure 3 were corrected for zero-point vibrational energies calculated at B3LYP.
72. N. Heinrich, H. Schwarz, in Ion and Cluster Ion Spectroscopy and Structure (Ed.:, J. P. Maier,), Elsevier, Amsterdam, 1989, p. 329.
73. For the electrophilic nature of cationic zinc-alkyl compounds, see
74. J. E. Fleckenstein, K. Koszinowski, Chem. Eur. J. 2009, 15, 12745-12753
75. F. Dreiocker, J. Oomens, A. J. H. M. Meijer, B. T. Pickup, R. F. W. Jackson, M. Schäfer, J. Org. Chem. 2010, 75, 1203-1213.
76. D. Schröder, H. Schwarz, S. Schenk, E. Anders, Angew. Chem. 2003, 115, 5241-5244
77. Angew. Chem. Int. Ed. 2003, 42, 5087-5090.
78. -):, Y. Dede, X. Zhang, M. Schlangen, H. Schwarz, M.-H. Baik, J. Am. Chem. Soc. 2009, 131, 12634-12642.
79. A. I. Boldyrev, J. Simons, J. Chem. Phys. 1992, 97, 6621-6627
80. H. Hopper, M. Lococo, O. Dolgounitcheva, V. G. Zakrzewski, J. V. Ortiz, J. Am. Chem. Soc. 2000, 122, 12813-12818.
81. D. K. Bohme, L. B. Young, J. Am. Chem. Soc. 1970, 92, 7354-7359
82. W. N. Olmstead, J. I. Brauman, J. Am. Chem. Soc. 1977, 99, 4219-4228
83. C. H. Depuy, S. Gronert, A. Mullin, V. M. Bierbaum, J. Am. Chem. Soc. 1990, 112, 8650-8655
84. N2 Mechanism, Wiley, New York, 1992
85. M. Bühl, H. F. Schaefer III, J. Am. Chem. Soc. 1993, 115, 9143-9147
86. E. Uggerud, J. Chem. Soc. Perkin Trans. 2 1999, 1459-1463
87. J. M. Gonzales, R. S. Cox, S. T. Brown, W. D. Allen, H. F. Schaefer III, J. Phys. Chem. A 2001, 105, 11327-11346
88. J. K. Laerdahl, E. Uggerud, Int. J. Mass Spectrom. 2002, 214, 277-314
89. J. M. Gonzales, C. Pak, R. S. Cox, W. D. Allen, H. F. Schaefer III, A. G. Csaszar, G. Tarczay, Chem. Eur. J. 2003, 9, 2173-2192
90. J. M. Gonzales, W. D. Allen, H. F. Schaefer III, J. Phys. Chem. A 2005, 109, 10613-10628
91. M. Swart, M. Solà, F. M. Bickelhaupt, J. Comput. Chem. 2007, 28, 1551-1560
92. A. P. Bento, M. Solà, F. M. Bickelhaupt, J. Chem. Theory Comput. 2008, 4, 929-940
93. R. H. Wu, T. B. McMahon, Mass Spectrom. Rev. 2009, 28, 546-585
94. I. Fernández, G. Frenking, E. Uggerud, Chem. Eur. J. 2009, 15, 2166-2175
95. E. Uggerud, Pure Appl. Chem. 2009, 81, 709-717
96. S. B. Liu, H. Hu, L. G. Pederset, J. Phys. Chem. A 2010, 114, 5913-5918
97. M. Swart, M. Solà, F. M. Bickelhaupt, J. Chem. Theory Comput. 2010, 6, 3145-3152.
98. N2 process, see
99. W. T. Huntress, Jr., R. F. Pinizzotto, Jr., J. B. Laudenslager, J. Am. Chem. Soc. 1973, 95, 4107-4115
100. C. P. K. Smith, M. Saunders, R. J. Cross, Jr., J. Am. Chem. Soc. 1976, 98, 1324-1330
101. D. Smith, N. G. Adams, Chem. Phys. Lett. 1977, 47, 145-149.
102. J. B. Schilling, W. A. Goddard, J. L. Beauchamp, J. Am. Chem. Soc. 1987, 109, 5573-5580
103. V. G. Zakrzewski, J. V. Ortiz, J. Chem. Phys. 1994, 100, 6508-6513
104. C. X. Yao, F. TureÄek, Phys. Chem. Chem. Phys. 2005, 7, 912-920.
105. C. Trage, D. Schröder, H. Schwarz, Chem. Eur. J. 2005, 11, 619-627.
106. M. Schlangen, H. Schwarz, D. Schröder, Helv. Chim. Acta 2007, 90, 847-853.
107. G. N. Khairallah, E. J. H. Yoo, R. A. J. O'Hair, Organometallics 2010, 29, 1238-1245
108. for the generation of organometallic anions, see, K. Koszinowski, P. Böhrer, Organometallics 2009, 28, 771-779.
109. T. J. Shi, K. W. M. Siu, A. C. Hopkinson, Int. J. Mass Spectrom. 2006, 255, 251-264.
110. http://www.sisweb.com/mstools/isotope.htm.
111. C. Trage, M. Diefenbach, D. Schröder, H. Schwarz, Chem. Eur. J. 2006, 12, 2454-2464
112. D. Schröder, M. Engeser, H. Schwarz, E. C. E. Rosenthal, J. Döbler, J. Sauer, Inorg. Chem. 2006, 45, 6235-6245
113. P. Gruene, C. Trage, D. Schröder, H. Schwarz, Eur. J. Inorg. Chem. 2006, 4546-4552.
114. 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. Montgomery, J. A., 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, N. J. 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, Ã. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian09, RevisionA.1, Gaussian Inc. Wallingford CT, 2009.
115. F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.
116. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789
117. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
118. K. Raghavachari, G. W. Trucks, J. A. Pople, M. Head-Gordon, Chem. Phys. Lett. 1989, 157, 479-483.
119. K. Fukui, J. Phys. Chem. 1970, 74, 4161-4163
120. K. Fukui, Acc. Chem. Res. 1981, 14, 363-368
121. C. Gonzalez, H. B. Schlegel, J. Phys. Chem. 1990, 94, 5523-5527.