Volume 52, Issue 16 pp. 4380-4383

Communication

Microhydration Effects on the Intermediates of the S_N2 Reaction of Iodide Anion with Methyl Iodide^†

Keisuke Doi,

Keisuke Doi

Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima 739-8526 (Japan)

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Eijiro Togano,

Eijiro Togano

Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima 739-8526 (Japan)

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Dr. Sotiris S. Xantheas,

Dr. Sotiris S. Xantheas

Chemical and Materials Sciences Division, Pacific Northwest National Laboratory, Richland, WA 99352 (USA)

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Ryuzo Nakanishi,

Ryuzo Nakanishi

Department of Basic Science, Graduate School of Arts and Sciences, The University of Tokyo, Tokyo 153-8902 (Japan)

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Prof. Takashi Nagata,

Prof. Takashi Nagata

Department of Basic Science, Graduate School of Arts and Sciences, The University of Tokyo, Tokyo 153-8902 (Japan)

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Prof. Takayuki Ebata,

Prof. Takayuki Ebata

Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima 739-8526 (Japan)

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Dr. Yoshiya Inokuchi,

Corresponding Author

Dr. Yoshiya Inokuchi

[email protected]

Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima 739-8526 (Japan)

Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima 739-8526 (Japan)===Search for more papers by this author

Keisuke Doi,

Keisuke Doi

Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima 739-8526 (Japan)

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Eijiro Togano,

Eijiro Togano

Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima 739-8526 (Japan)

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Dr. Sotiris S. Xantheas,

Dr. Sotiris S. Xantheas

Chemical and Materials Sciences Division, Pacific Northwest National Laboratory, Richland, WA 99352 (USA)

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Ryuzo Nakanishi,

Ryuzo Nakanishi

Department of Basic Science, Graduate School of Arts and Sciences, The University of Tokyo, Tokyo 153-8902 (Japan)

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Prof. Takashi Nagata,

Prof. Takashi Nagata

Department of Basic Science, Graduate School of Arts and Sciences, The University of Tokyo, Tokyo 153-8902 (Japan)

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Prof. Takayuki Ebata,

Prof. Takayuki Ebata

Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima 739-8526 (Japan)

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Dr. Yoshiya Inokuchi,

Corresponding Author

Dr. Yoshiya Inokuchi

[email protected]

Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima 739-8526 (Japan)

Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima 739-8526 (Japan)===Search for more papers by this author

First published: 30 January 2013

https://doi.org/10.1002/anie.201207697

Citations: 30

^†

This work is supported by Grant-in-Aids (21350016) for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology (MEXT) of Japan. S.S.X. acknowledges support from the US Department of Energy, Office of Basic Energy Sciences, Division of Chemical Sciences, Geosciences & Biosciences. Pacific Northwest National Laboratory (PNNL) is a multiprogram national laboratory operated for the DOE by Battelle.

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Graphical Abstract

Water gets in the way: Hydrated I⁻(CH₃I) complexes, I⁻(CH₃I)(H₂O)_1–3, are investigated by IR photodissociation spectroscopy to examine the stable structures of the intermediates of the I⁻+CH₃I→ICH₃+I⁻ S_N2 reaction under hydrated conditions. The structures and the energetics of the complexes suggest that just one or two H₂O molecules will effectively inhibit this S_N2 reaction.

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References

1For example, see: K. P. C. Vollhardt, N. E. Schore, Organic Chemistry, 4th ed., W. H. Freeman and Co., New York, 2003.
Google Scholar
2
2aW. N. Olmstead, J. I. Brauman, J. Am. Chem. Soc. 1977, 99, 4219;
10.1021/ja00455a002
CAS Web of Science® Google Scholar
2bP. Manikandan, J. Zhang, W. L. Hase, J. Phys. Chem. A 2012, 116, 3061.
10.1021/jp211387c
CAS PubMed Web of Science® Google Scholar
3P. Beronius, Acta Chem. Scand. 1961, 15, 1151.
10.3891/acta.chem.scand.15-1151
CAS Web of Science® Google Scholar
4K. Morokuma, J. Am. Chem. Soc. 1982, 104, 3732.
10.1021/ja00377a037
CAS Web of Science® Google Scholar
5
5aD. M. Cyr, L. A. Posey, G. A. Bishea, C.-C. Han, M. A. Johnson, J. Am. Chem. Soc. 1991, 113, 9697;
10.1021/ja00025a059
CAS Web of Science® Google Scholar
5bC. E. H. Dessent, M. A. Johnson, J. Am. Chem. Soc. 1997, 119, 5067;
10.1021/ja970583l
CAS Web of Science® Google Scholar
5cP. Ayotte, J. Kim, J. A. Kelley, S. B. Nielsen, M. A. Johnson, J. Am. Chem. Soc. 1999, 121, 6950;
10.1021/ja990814j
CAS Web of Science® Google Scholar
5dS. Horvath, A. B. McCoy, B. M. Elliott, G. H. Weddle, J. R. Roscioli, M. A. Johnson, J. Phys. Chem. A 2010, 114, 1556, and references therein.
10.1021/jp9088782
CAS PubMed Web of Science® Google Scholar
6A. J. Parker, Chem. Rev. 1969, 69, 1.
10.1021/cr60257a001
CAS Web of Science® Google Scholar
7NIST Chemistry WebBook, http://webbook.nist.gov/chemistry/.
Google Scholar
8
8aX. Chen, C. K. Regan, S. L. Craig, E. H. Krenske, K. N. Houk, W. L. Jorgensen, J. I. Brauman, J. Am. Chem. Soc. 2009, 131, 16162;
10.1021/ja9053459
CAS PubMed Web of Science® Google Scholar
8bR. A. J. O’Hair, G. E. Davico, J. Hacaloglu, T. T. Dang, C. H. DePuy, V. M. Bierbaum, J. Am. Chem. Soc. 1994, 116, 3609;
10.1021/ja00087a061
CAS Web of Science® Google Scholar
8cD. K. Bohme, G. I. Mackay, J. Am. Chem. Soc. 1981, 103, 978;
10.1021/ja00394a062
CAS Web of Science® Google Scholar
8dD. K. Bohme, A. B. Raksit, J. Am. Chem. Soc. 1984, 106, 3447;
10.1021/ja00324a011
CAS Web of Science® Google Scholar
8eD. K. Bohme, A. B. Raksit, Can. J. Chem. 1985, 63, 3007;
10.1139/v85-499
CAS Web of Science® Google Scholar
8fM. Henchman, J. F. Paulson, P. M. Hierl, J. Am. Chem. Soc. 1983, 105, 5509;
10.1021/ja00354a071
CAS Web of Science® Google Scholar
8gM. Henchman, P. M. Hierl, J. F. Paulson, J. Am. Chem. Soc. 1985, 107, 2812;
10.1021/ja00295a047
CAS Web of Science® Google Scholar
8hP. M. Hierl, A. F. Ahrens, M. Henchman, A. A. Viggiano, J. F. Paulson, J. Am. Chem. Soc. 1986, 108, 3142.
10.1021/ja00271a074
CAS Web of Science® Google Scholar
9Y. Kobayashi, Y. Inokuchi, T. Ebata, J. Chem. Phys. 2008, 128, 164319.
10.1063/1.2913157
CAS PubMed Web of Science® Google Scholar
10Gaussian 09, Revision A.02, Frisch M. J. et al., Gaussian, Inc., Wallingford CT, 2009.
Google Scholar
11M. Valiev, E. J. Bylaska, N. Govind, K. Kowalski, T. P. Straatsma, H. J. J. van Dam, D. Wang, J. Nieplocha, E. Apra, T. L. Windus, W. A. de Jong, Comput. Phys. Commun. 2010, 181, 1477.
10.1016/j.cpc.2010.04.018
CAS Web of Science® Google Scholar

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Volume52, Issue16

April 15, 2013

Pages 4380-4383

Microhydration Effects on the Intermediates of the S_N2 Reaction of Iodide Anion with Methyl Iodide^†

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Microhydration Effects on the Intermediates of the SN2 Reaction of Iodide Anion with Methyl Iodide†

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Microhydration Effects on the Intermediates of the S_N2 Reaction of Iodide Anion with Methyl Iodide^†