Does nitroalkane anomaly exist in the gas phase? [7]

Journal of the American Chemical Society

Volumn 121, Issue 43, 1999, Pages 10223-10224

  Yamataka, Hiroshi ^a   Mustanir, ^b   Mishima, Masaaki ^b  

^a OSAKA UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; HYDROGEN CYANIDE; NITROALKANE; SOLVENT;

CHEMICAL REACTION; CONTROLLED STUDY; ENERGY; ENTHALPY; GAS; LETTER; PROTON TRANSPORT;

EID: 0033520682     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992572t     Document Type: Letter

References (27)

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6. Richard, J. P.; Williams, G.; Gao, J. J. Am. Chem. Soc. 1999, 121, 715.
7. For more general argument for anomalous Brønsted coefficient in proton-transfer reactions, see: Kresge, A. J. J. Am. Chem. Soc. 1971, 93, 413. Marcus, R. A. J. Am. Chem. Soc. 1969, 91, 7224. Murdoch, J. R. J. Am. Chem. Soc. 1972, 94, 4410. Eigen, M. Angew. Chem., Int. Ed. Engl. 1964, 3, 1. Pross, A.; Shaik, S. S. J. Am. Chem. Soc. 1982, 104, 1129. Bordwell, F. G.; Hughes, D. K. J. Am. Chem. Soc. 1985, 107, 4737. Yamataka, H.; Nagase, S. J. Org. Chem. 1988, 53, 3232. Ritchie, C. D.; Uschold, R. E. J. Am. Chem. Soc. 1968, 90, 3415. Murdoch, J. R.; McMiller, D. F. J. Am. Chem. Soc. 1982, 104, 600.
8. For more general argument for anomalous Brønsted coefficient in proton-transfer reactions, see: Kresge, A. J. J. Am. Chem. Soc. 1971, 93, 413. Marcus, R. A. J. Am. Chem. Soc. 1969, 91, 7224. Murdoch, J. R. J. Am. Chem. Soc. 1972, 94, 4410. Eigen, M. Angew. Chem., Int. Ed. Engl. 1964, 3, 1. Pross, A.; Shaik, S. S. J. Am. Chem. Soc. 1982, 104, 1129. Bordwell, F. G.; Hughes, D. K. J. Am. Chem. Soc. 1985, 107, 4737. Yamataka, H.; Nagase, S. J. Org. Chem. 1988, 53, 3232. Ritchie, C. D.; Uschold, R. E. J. Am. Chem. Soc. 1968, 90, 3415. Murdoch, J. R.; McMiller, D. F. J. Am. Chem. Soc. 1982, 104, 600.
9. For more general argument for anomalous Brønsted coefficient in proton-transfer reactions, see: Kresge, A. J. J. Am. Chem. Soc. 1971, 93, 413. Marcus, R. A. J. Am. Chem. Soc. 1969, 91, 7224. Murdoch, J. R. J. Am. Chem. Soc. 1972, 94, 4410. Eigen, M. Angew. Chem., Int. Ed. Engl. 1964, 3, 1. Pross, A.; Shaik, S. S. J. Am. Chem. Soc. 1982, 104, 1129. Bordwell, F. G.; Hughes, D. K. J. Am. Chem. Soc. 1985, 107, 4737. Yamataka, H.; Nagase, S. J. Org. Chem. 1988, 53, 3232. Ritchie, C. D.; Uschold, R. E. J. Am. Chem. Soc. 1968, 90, 3415. Murdoch, J. R.; McMiller, D. F. J. Am. Chem. Soc. 1982, 104, 600.
10. For more general argument for anomalous Brønsted coefficient in proton-transfer reactions, see: Kresge, A. J. J. Am. Chem. Soc. 1971, 93, 413. Marcus, R. A. J. Am. Chem. Soc. 1969, 91, 7224. Murdoch, J. R. J. Am. Chem. Soc. 1972, 94, 4410. Eigen, M. Angew. Chem., Int. Ed. Engl. 1964, 3, 1. Pross, A.; Shaik, S. S. J. Am. Chem. Soc. 1982, 104, 1129. Bordwell, F. G.; Hughes, D. K. J. Am. Chem. Soc. 1985, 107, 4737. Yamataka, H.; Nagase, S. J. Org. Chem. 1988, 53, 3232. Ritchie, C. D.; Uschold, R. E. J. Am. Chem. Soc. 1968, 90, 3415. Murdoch, J. R.; McMiller, D. F. J. Am. Chem. Soc. 1982, 104, 600.
11. For more general argument for anomalous Brønsted coefficient in proton-transfer reactions, see: Kresge, A. J. J. Am. Chem. Soc. 1971, 93, 413. Marcus, R. A. J. Am. Chem. Soc. 1969, 91, 7224. Murdoch, J. R. J. Am. Chem. Soc. 1972, 94, 4410. Eigen, M. Angew. Chem., Int. Ed. Engl. 1964, 3, 1. Pross, A.; Shaik, S. S. J. Am. Chem. Soc. 1982, 104, 1129. Bordwell, F. G.; Hughes, D. K. J. Am. Chem. Soc. 1985, 107, 4737. Yamataka, H.; Nagase, S. J. Org. Chem. 1988, 53, 3232. Ritchie, C. D.; Uschold, R. E. J. Am. Chem. Soc. 1968, 90, 3415. Murdoch, J. R.; McMiller, D. F. J. Am. Chem. Soc. 1982, 104, 600.
12. For more general argument for anomalous Brønsted coefficient in proton-transfer reactions, see: Kresge, A. J. J. Am. Chem. Soc. 1971, 93, 413. Marcus, R. A. J. Am. Chem. Soc. 1969, 91, 7224. Murdoch, J. R. J. Am. Chem. Soc. 1972, 94, 4410. Eigen, M. Angew. Chem., Int. Ed. Engl. 1964, 3, 1. Pross, A.; Shaik, S. S. J. Am. Chem. Soc. 1982, 104, 1129. Bordwell, F. G.; Hughes, D. K. J. Am. Chem. Soc. 1985, 107, 4737. Yamataka, H.; Nagase, S. J. Org. Chem. 1988, 53, 3232. Ritchie, C. D.; Uschold, R. E. J. Am. Chem. Soc. 1968, 90, 3415. Murdoch, J. R.; McMiller, D. F. J. Am. Chem. Soc. 1982, 104, 600.
13. For more general argument for anomalous Brønsted coefficient in proton-transfer reactions, see: Kresge, A. J. J. Am. Chem. Soc. 1971, 93, 413. Marcus, R. A. J. Am. Chem. Soc. 1969, 91, 7224. Murdoch, J. R. J. Am. Chem. Soc. 1972, 94, 4410. Eigen, M. Angew. Chem., Int. Ed. Engl. 1964, 3, 1. Pross, A.; Shaik, S. S. J. Am. Chem. Soc. 1982, 104, 1129. Bordwell, F. G.; Hughes, D. K. J. Am. Chem. Soc. 1985, 107, 4737. Yamataka, H.; Nagase, S. J. Org. Chem. 1988, 53, 3232. Ritchie, C. D.; Uschold, R. E. J. Am. Chem. Soc. 1968, 90, 3415. Murdoch, J. R.; McMiller, D. F. J. Am. Chem. Soc. 1982, 104, 600.
14. For more general argument for anomalous Brønsted coefficient in proton-transfer reactions, see: Kresge, A. J. J. Am. Chem. Soc. 1971, 93, 413. Marcus, R. A. J. Am. Chem. Soc. 1969, 91, 7224. Murdoch, J. R. J. Am. Chem. Soc. 1972, 94, 4410. Eigen, M. Angew. Chem., Int. Ed. Engl. 1964, 3, 1. Pross, A.; Shaik, S. S. J. Am. Chem. Soc. 1982, 104, 1129. Bordwell, F. G.; Hughes, D. K. J. Am. Chem. Soc. 1985, 107, 4737. Yamataka, H.; Nagase, S. J. Org. Chem. 1988, 53, 3232. Ritchie, C. D.; Uschold, R. E. J. Am. Chem. Soc. 1968, 90, 3415. Murdoch, J. R.; McMiller, D. F. J. Am. Chem. Soc. 1982, 104, 600.
15. For more general argument for anomalous Brønsted coefficient in proton-transfer reactions, see: Kresge, A. J. J. Am. Chem. Soc. 1971, 93, 413. Marcus, R. A. J. Am. Chem. Soc. 1969, 91, 7224. Murdoch, J. R. J. Am. Chem. Soc. 1972, 94, 4410. Eigen, M. Angew. Chem., Int. Ed. Engl. 1964, 3, 1. Pross, A.; Shaik, S. S. J. Am. Chem. Soc. 1982, 104, 1129. Bordwell, F. G.; Hughes, D. K. J. Am. Chem. Soc. 1985, 107, 4737. Yamataka, H.; Nagase, S. J. Org. Chem. 1988, 53, 3232. Ritchie, C. D.; Uschold, R. E. J. Am. Chem. Soc. 1968, 90, 3415. Murdoch, J. R.; McMiller, D. F. J. Am. Chem. Soc. 1982, 104, 600.
16. All calculations were carried out with the Gaussian 94 package of programs, and full frequency analyses were done to confirm that the calculated structures are on a minimum or saddle point on the potential energy surface. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.: Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; DeFrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez C.; Pople, J. A. Gaussian 94; Gaussian Inc.: Pittsburgh, PA, 1995.
17. (CH3NO2)) are as follows: 1.310, 0.756; 1.380, 0.755; 1.948, 0.827; 2.441, 0.752; 2.466, 0.753; 4.142, 0.726. Mean value = 0.76 ± 0.03. Marshall, A. G.; Wang, T.-C. L.; Ricca, T. L. J. Am. Chem. Soc., 1985, 107, 7983; Cody, R. B. Analysis 1988, 16, 30. Guan, S.; Marshall, A. G. Int. J. Mass Spectrom. Ion Process 1997, 157/158, 5.
18. (CH3NO2)) are as follows: 1.310, 0.756; 1.380, 0.755; 1.948, 0.827; 2.441, 0.752; 2.466, 0.753; 4.142, 0.726. Mean value = 0.76 ± 0.03. Marshall, A. G.; Wang, T.-C. L.; Ricca, T. L. J. Am. Chem. Soc., 1985, 107, 7983; Cody, R. B. Analysis 1988, 16, 30. Guan, S.; Marshall, A. G. Int. J. Mass Spectrom. Ion Process 1997, 157/158, 5.
19. (CH3NO2)) are as follows: 1.310, 0.756; 1.380, 0.755; 1.948, 0.827; 2.441, 0.752; 2.466, 0.753; 4.142, 0.726. Mean value = 0.76 ± 0.03. Marshall, A. G.; Wang, T.-C. L.; Ricca, T. L. J. Am. Chem. Soc., 1985, 107, 7983; Cody, R. B. Analysis 1988, 16, 30. Guan, S.; Marshall, A. G. Int. J. Mass Spectrom. Ion Process 1997, 157/158, 5.
20. Bartmess, J. E. Negative Ion Energetics Data. In NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Mallard, W. G., Linstrom, P. J., Eds.; November 1998; National Institute of Standards and Technology: Gaithersburg MD, 20899 (http://webbook.nist.gov).
21. Su, T.; Bowers, M. T. J. Chem. Phys. 1973, 58, 3027.
22. Bernasconi, C. F. Adv. Phys. Org. Chem. 1992, 27, 116. Bernasconi, C. F. Acc. Chem. Res. 1992, 25, 9.
23. Bernasconi, C. F. Adv. Phys. Org. Chem. 1992, 27, 116. Bernasconi, C. F. Acc. Chem. Res. 1992, 25, 9.
24. 2 with benzoate ion in DMSO showed the Brønsted α of 0.92, an intermediate value between those in water (1.54) and the gas phase (0.51). Keeffe, J. R.; Morey, J.; Palmer, C. A.; Lee, J. C. J. Am. Chem. Soc. 1979, 101, 1295.
25. 2 with benzoate ion in DMSO showed the Brønsted α of 0.92, an intermediate value between those in water (1.54) and the gas phase (0.51). Keeffe, J. R.; Morey, J.; Palmer, C. A.; Lee, J. C. J. Am. Chem. Soc. 1979, 101, 1295.
26. 2 with benzoate ion in DMSO showed the Brønsted α of 0.92, an intermediate value between those in water (1.54) and the gas phase (0.51). Keeffe, J. R.; Morey, J.; Palmer, C. A.; Lee, J. C. J. Am. Chem. Soc. 1979, 101, 1295.
27. 2 with benzoate ion in DMSO showed the Brønsted α of 0.92, an intermediate value between those in water (1.54) and the gas phase (0.51). Keeffe, J. R.; Morey, J.; Palmer, C. A.; Lee, J. C. J. Am. Chem. Soc. 1979, 101, 1295.