Mechanism Research of Reactions of Metal Carbides and Carbenes Cation[M-X] +(M=Au, Ag, Cu; X=C, CH2) with Methane

doi:10.7503/cjcu20170039

Abstract

Abstract:

In this article, the reaction mechanism of the cation[Au(CH₂)] ⁺ and methane was investigated at the CCSD(T)-REL//B2GP-PLYP level of theory initially. A detailed analysis of geometric structure changes during the C-H bond activation was given. As a major result, based on natural bond orbital(NBO) charge and molecular orbital analysis, a hydride transfer mechanistic scenario from methane to[Au(CH₂)] ⁺ was identified unambiguously. Methane activation has been identified among its reaction with[M-X] ⁺(M=Au, Ag, Cu; X=C, CH₂). Analysis for the inherent factors during the reaction of methane as a hydrogen donor is given. The M-X bond energy and the low-lying vacant orbital directly involved in the reaction of the active center C play an important role on the reaction activity, and both mediated microscopic mechanism. This study may provide important guidance for the rational design of catalysts.

Key words: C-H Bond activation, Carbene cation, Proton transfer, Hydrogen atom transfer, Hydride transfer

CLC Number:

O641

TrendMD:

SUN Xiaoli, MENG Lingmin, JIN Mingxing, LI Jilai. Mechanism Research of Reactions of Metal Carbides and Carbenes Cation[M-X] ⁺(M=Au, Ag, Cu; X=C, CH₂) with Methane[J]. Chem. J. Chinese Universities, 2017, 38(8): 1406.

References

[1] Arndtsen B. A., Bergman R. G., Mobley T. A., Peterson T. H., Acc. Chem. Res., 1995, 28, 154-162
[2] Dietl N., Schlangen M., Schwarz H., Angew. Chem. Int. Ed., 2012, 51, 5544-5555
[3] Schr der D., Roithová J., Angew. Chem. Int. Ed., 2006, 45, 5705-5708
[4] Dietl N., Paul R., Linde C., Schlangen M., Beyer M. K., Schwarz H., Angew. Chem. Int. Ed., 2011, 50, 4966-4969
[5] Wang Z. C., Dietl N., Kretschmer R., Ma J. B., Weiske T., Schlangen M., Schwarz H., Angew. Chem. Int. Ed., 2012, 51, 3703-3707
[6] Wang Z. C., Weiske T., Kretschmer R., Schlangen M., Kaupp M., Schwarz H., J. Am. Chem. Soc., 2011, 133, 16930-16937
[7] Feyel S., D bler J., H ckendorf R. F., Beyer M. K., Sauer J., Schwarz H., Angew. Chem. Int. Ed., 2008, 47, 1946-1950
[8] Feyel S., D bler J., Schr der D., Sauer J., Schwarz H., Angew. Chem. Int. Ed., 2006, 45, 4681-4685
[9] Li J., Wu X. N., Schlangen M., Zhou S., González-Navarrete P., Tang S., Schwarz H., Angew. Chem. Int. Ed., 2015, 54, 5074-5078
[10] Lai W., Li C., Chen H., Shaik S., Angew. Chem. Int. Ed., 2012, 51, 5556-5578
[11] Schwarz H., González-Navarrete P., Li J., Schlangen M., Sun X., Weiske T., Zhou S., Organometallics, 2017, 36, 8-17
[12] Ma J. B., Xu L. L., Liu Q. Y., He S. G., Angew. Chem. Int. Ed., 2016, 55, 4947-4951
[13] Zhou S., Li J., Schlangen M., Schwarz H., Angew. Chem. Int. Ed., 2016, 55, 7685-7688
[14] Zhou S., Li J., Wu X. N., Schlangen M., Schwarz H., Angew. Chem. Int. Ed., 2016, 55, 441-444
[15] Sun X., Zhou S., Schlangen M., Schwarz H., Chem. Eur. J., 2016, 22, 14257-14263
[16] Li J., Zhou S., Zhang J., Schlangen M., Weiske T., Usharani D., Shaik S., Schwarz H., J. Am. Chem. Soc., 2016, 138, 7973-7981
[17] Blanksby S. J., Ellison G. B., Acc. Chem. Res., 2003, 36, 255-263
[18] Graul S. T., Squires R. R., J. Am. Chem. Soc., 1990, 112, 2517-2529
[19] Plessis P., Marmet P., Dutil R., J. Phys. B, 1983, 16, 1283-1294
[20] Olivos-Suarez A. I., Szécsényi À., Hensen E. J. M., Ruiz-Martinez J., Pidko E. A., Gascon J., ACS Catal., 2016, 6, 2965-2981
[21] Schwarz H., Chem. Phys. Lett., 2015, 629, 91-101
[22] Coperet C., Chem. Rev., 2010, 110, 656-680
[23] Ess D. H., Nielsen R. J., Goddard W. A., Periana R. A., J. Am. Chem. Soc., 2009, 131, 11686-11688
[24] Schr der D., Schwarz H., Proc. Natl. Acad. Sci. USA, 2008, 105, 18114-18119
[25] Vastine B. A., Hall M. B., J. Am. Chem. Soc., 2007, 129, 12068-12069
[26] Werkema E. L., Maron L., Eisenstein O., Andersen R. A., J. Am. Chem. Soc., 2007, 129, 2529-2541
[27] Geng C., Li J., Weiske T., Schlangen M., Shaik S., Schwarz H., J. Am. Chem. Soc., 2017, 139, 1684-1689
[28] Li J., Zhou S., Schlangen M., Weiske T., Schwarz H., Angew. Chem. Int. Ed., 2016, 55, 13072-13075
[29] Li J., Zhou S., Schlangen M., Weiske T., Schwarz H., Chemistry Select, 2016, 3, 444-447
[30] Li J., Zhou S., Wu X. N., Tang S., Schlangen M., Schwarz H., Angew. Chem. Int. Ed., 2015, 54, 11861-11864
[31] Kang R. H., Chen H., Shaik S., Yao J. N., J. Chem. Theory. Comput., 2011, 7, 4002-4011
[32] Karton A., Tarnopolsky A., Lamère J. F., Schatz G. C., Martin J. M. L., J. Phys. Chem. A, 2008, 112, 12868-12886
[33] Grimme S., Antony J., Ehrlich S., Krieg H., J. Chem. Phys., 2010, 132, 154104
[34] Truhlar D. G., Gordon M. S., Science, 1990, 249, 491-498
[35] Gonzalez C., Schlegel H. B., J. Phys. Chem., 1990, 94, 5523-5527
[36] Fukui K., Acc. Chem. Res., 1981, 14, 363-368
[37] Fukui K., J. Phys. Chem., 1970, 74, 4161-4163
[38] Reed A. E., Curtiss L. A., Weinhold F. A., Chem. Rev., 1988, 88, 899-926
[39] Carpenter J. E., Weinhold F. A., J. Mol. Struc. Theochem., 1988, 169, 41-62
[40] Reed A. E., Weinstock R. B., Weinhold F. A., J. Chem. Phys., 1985, 83, 735-746
[41] Reed A. E., Weinhold F. A., J. Chem. Phys., 1985, 83, 1736-1740
[42] Reed A. E., Weinhold F. A., J. Chem. Phys., 1983, 78, 4066-4073
[43] Foster J. P., Weinhold F. A., J. Am. Chem. Soc., 1980, 102, 7211-7218
[44] Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Scalmani G., Barone V., Mennucci B., Petersson G. A., Nakatsuji H., Caricato M., Li X., Hratchian H. P., Izmaylov A. F., Bloino J., Zheng G., Sonnenberg J. L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., J. A. Montgomery J., Peralta J. E., Ogliaro F., Bearpark M., Heyd J. J., Brothers E., Kudin K. N., Staroverov V. N., Keith T., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J. C., Iyengar S. S., Tomasi J., Cossi M., Rega N., Millam J. M., Klene M., Knox J. E., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Martin R. L., Morokuma K., Zakrzewski V. G., Voth G. A., Salvador P., Dannenberg J. J., Dapprich S., Daniels A. D., Farkas O., Foresman J. B., Ortiz J. V., Cioslowski J., Fox D. J., Gaussian 09, Revision D.01, Gaussian Inc., Wallingford CT, 2013
[45] Reiher M., WIREs Comput. Mol. Sci., 2012, 2, 139-149
[46] Peterson A. K., Puzzarini C., Theor. Chem. Acc., 2005, 114, 283-296
[47] Jansen G., Hess B. A., Phys. Rev. A, 1989, 39, 6016-6017
[48] Hess B. A., Phys. Rev. A, 1986, 33, 3742-3748
[49] Hess B. A., Phys. Rev. A, 1985, 32, 756-763
[50] Werner H. J., Knowles P. J., Knizia G., Manby F. R., Schütz M., Celani P., Korona T., Lindh R., Mitrushenkov A., Rauhut G., Shamasundar K. R., Adler T. B., Amos R. D., Bernhardsson A., Berning A., Cooper D. L., Deegan M. J. O., Dobbyn A. J., Eckert F., Goll E., Hampel C., Hesselmann A., Hetzer G., Hrenar T., Jansen G., K ppl C., Liu Y., Lloyd A. W., Mata R. A., May A. J., McNicholas S. J., Meyer W., Mura M. E., Nicklass A., O'Neill D. P., Palmieri P., Peng D., Pflüger K., Pitzer R., Reiher M., Shiozaki T., Stoll H., Stone A. J., Tarroni R., Thorsteinsson T., Wang M., Molpro:A Package of Ab Initio Programs, Version 2012.1; http://www.molpro.net
[51] Perdew J. P., Phys. Rev. B, 1986, 33, 8822-8824
[52] Tao J., Perdew J. P., Staroverov V. N., Scuseria G. E., Phys. Rev. Lett., 2003, 91, 146401
[53] Perdew J. P., Burke K., Ernzerhof M., Phys. Rev. Lett., 1996, 77, 3865-3868
[54] Chai J. D., Head-Gordon M., Phys. Chem. Chem. Phys., 2008, 10, 6615-6620
[55] Kim K., Jordan K. D., J. Phys. Chem., 1994, 98, 10089-10094
[56] Becke A. D., J. Chem. Phys., 1993, 98, 5648-5652
[57] Xu X., Goddard W. A., Proc. Natl. Acad. Sci. USA, 2004, 101, 2673-2677
[58] Adamo C., Barone V., J. Chem. Phys., 1999, 110, 6158-6170
[59] Adamo C., Barone V., J. Chem. Phys., 1998, 108, 664-675
[60] Boese A. D., Martin J. M. L., J. Chem. Phys., 2004, 121, 3405-3416
[61] Becke A. D., J. Chem. Phys., 1993, 98, 1372-1377
[62] Chai J. D., Head-Gordon M., J. Chem. Phys., 2008, 128, 084106
[63] Peverati R., Truhlar D. G., J. Phys. Chem. Lett., 2011, 2, 2810-2817
[64] Da Costa H. F. M., Trsic M., Mohallem J. R., Molecular Physics, 1987, 62, 91-95
[65] Diercksen G. H. F., Sadlej A. J., Chem. Phys., 1981, 61, 293-304
[66] Barone V., J. Chem. Phys., 2005, 122, 014108
[67] Cammi R., Mennucci B., Tomasi J., J. Phys. Chem. A, 1999, 103, 9100-9108
[68] Neese F., WIREs Comput. Mol. Sci., 2012, 2, 73-78
[69] Li J., Andreji c' M., Mata R. A., Ryde U., Eur. J. Inorg. Chem., 2015, 3580-3589
[70] Li J. L., Mata R. A., Ryde U., J. Chem. Theory. Comput., 2013, 9, 1799-1807
[71] Li J., Geng C., Huang X., Sun C., J. Chem. Theory. Comput., 2006, 2, 1551-1564
[72] Sun X., Geng C., Huo R., Ryde U., Bu Y., Li J., J. Phys. Chem. B, 2014, 118, 1493-1500
[73] Geng C. Y., Ye S., Neese F., Angew. Chem. Int. Ed., 2010, 49, 5717-5720
[74] Groves J. T., Mcclusky G. A., J. Am. Chem. Soc., 1976, 98, 859-861
[75] Geng C., Ye S., Neese F., Dalton Trans., 2014, 43, 6079-6086
[76] Ye S., Geng C. Y., Shaik S., Neese F., Phys. Chem. Chem. Phys., 2013, 15, 8017-8030
[77] Li J. L., Zhang X., Huang X. R., Phys. Chem. Chem. Phys., 2012, 14, 246-256
[78] Doyle M. P., Duffy R. J., Ratnikov M. O., Zhou L., Chem. Rev., 2010, 110, 704-724
[79] Yoshikai N., Nakamura E., Adv. Synth. Catal., 2003, 345, 1159-1171
[80] Nakamura E., Yoshikai N., Yamanaka M., J. Am. Chem. Soc., 2002, 124, 7181-7192
[81] Davies H. M. L., Hansen T., Churchill M. R., J. Am. Chem. Soc., 2000, 122, 3063-3070
[82] Doyle M. P., Westrum L. J., Wolthuis W. N. E., See M. M., Boone W. P., Bagheri V., Pearson M. M., J. Am. Chem. Soc., 1993, 115, 958-964
[83] Li F. X., Armentrout P. B., J. Chem. Phys., 2006, 125, 133114
[84] Schwarz H., Isr. J. Chem., 2014, 54, 1413-1431
[85] Li J. L., Zhou S. D., Zhang J., Schlangen M., Usharani D., Shaik S., Schwarz H., J. Am. Chem. Soc., 2016, 138, 11368-11377
[86] Li J., Wu X. N., Zhou S., Tang S., Schlangen M., Schwarz H., Angew. Chem. Int. Ed., 2015, 54, 12298-12302

Mechanism Research of Reactions of Metal Carbides and Carbenes Cation[M-X] ⁺(M=Au, Ag, Cu; X=C, CH₂) with Methane

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