An Intuitive Electric-field Contribution Decomposition Model for Chemical Processes and Its Applications on Diels-Alder Reactions

doi:10.1007/s40242-020-0143-x

Chemical Research in Chinese Universities ›› 2020, Vol. 36 ›› Issue (6): 1241-1248.doi: 10.1007/s40242-020-0143-x

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An Intuitive Electric-field Contribution Decomposition Model for Chemical Processes and Its Applications on Diels-Alder Reactions

LIU Fengyi, LIU Minjuan

Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi'an 710062, P. R. China

Received:2020-04-16 Revised:2020-06-27 Online:2020-12-01 Published:2020-12-03
Contact: LIU Fengyi E-mail:fengyiliu@snnu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.21873060, 21473107) and the Fundamental Research Funds for the Central Universities of China(No.GK201901007).

Abstract

Abstract: External electric field(EEF) has shown its advantages in tuning chemical reaction as an efficient and feasible-to-control tool. In this paper, we explored the mechanisms of three EEF-regulated Diels-Alder reactions including two traditional-DA reactions to form two C-C single bonds and a hetero-DA reaction to form both a C-C and a C-O bond, respectively, and introduced an EEF contribution decomposition(ECD) model to understand how the EEF coupled with the intrinsic nuclear and electronic redistributions so as to affect chemical reaction. The ECD model, by decomposing the overall EEF effects into geometry re-equilibrium and static induction parts, can give a clear and quantitative picture of a physical quantity change upon EEF, as demonstrated on relative energies, activation barriers, charge distribution and dipole moments. The ECD analyses will shed light on the effective tuning of chemical reactions by the electric field.

Key words: Electric field, Diels-Alder reaction, Decomposition model

LIU Fengyi, LIU Minjuan. An Intuitive Electric-field Contribution Decomposition Model for Chemical Processes and Its Applications on Diels-Alder Reactions[J]. Chemical Research in Chinese Universities, 2020, 36(6): 1241-1248.

References

[1] Diels O., Alder K., Liebigs Ann. Chem., 1928, 460, 98
[2] Diels O., Blom J. H., Koll W., Liebigs Ann. Chem., 1925, 443, 242
[3] Sauer J., Sustmann R., Angew. Chem. Int. Ed., 1980, 19, 779
[4] Konovalov A. I., Russ. Chem. Rev., 1983, 52, 1064
[5] Xu L., Liu F., Xu L. W., Gao Z., Zhao Y. M., Org. Lett., 2016, 18, 3698
[6] Heravi M. M., Ahmadi T., Ghavidel M., Heidari B., Hamidi H., RSC Adv., 2015, 5, 101999
[7] Schmidt R. R., Acc. Chem. Res., 1986, 19, 250
[8] Cui H. L., Tanaka F., Chem. Eur. J., 2013, 19, 6213
[9] Meir R., Chen H., Lai W., Shaik S., ChemPhysChem, 2010, 11, 301
[10] Shaik S., Mandal D., Ramanan R., Nat. Chem., 2016, 8, 1091
[11] Aragonès A. C., Haworth N. L., Darwish N., Ciampi S., Bloomfield N. J., Wallace G. G., Diez-Perez I., Coote M. L., Nature, 2016, 531, 88
[12] Shaik S., Ramanan R., Danovich D., Mandal D., Chem. Soc. Rev., 2018, 47, 5125
[13] Aitken H. M., Coote M. L., Phys. Chem. Chem. Phys., 2018, 20, 10671
[14] Li Y., Li Y., Su Q., Wang B., Guo N., Liu F., Theor. Chem. Acc., 2017, 136, 27
[15] Schyman P., Lai W., Chen H., Wang Y., Shaik S., J. Am. Chem. Soc., 2011, 133, 7977
[16] Bhattacharyya K., Karmakar S., Datta A., Phys. Chem. Chem. Phys., 2017, 19, 22482
[17] Geng C., Li J., Weiske T., Schlangen M., Shaik S., Schwarz H., J. Am. Chem. Soc., 2017, 139, 1684
[18] Gorin C. F., Beh E. S., Bui Q. M., Dick G. R., Kanan M. W., J. Am. Chem. Soc., 2013, 135, 11257
[19] Akamatsu M., Sakai N., Matile S., J. Am. Chem. Soc., 2017, 139, 6558
[20] Ess D. H., Houk K. N., J. Am. Chem. Soc., 2007, 129, 10646
[21] Yang Y. F., Liang Y., Liu F., Houk K. N., J. Am. Chem. Soc., 2016, 138, 1660
[22] Bickrthlhaupt F. M., Houk K. N., Angew. Chem. Int. Ed., 2017, 56, 10070
[23] Cohen A. J., Mori-Sánchez P., Yang W., Chem. Rev., 2012, 112, 289
[24] Zhao Y., Truhlar D. G., Acc. Chem. Res., 2008, 41, 157
[25] Zhao Y., Truhlar D. G., Theor. Chem. Acc., 2008, 120, 215
[26] Grimme S., Wiley Interdiscip. Rev. Comput. Mol. Sci., 2011, 1, 211
[27] Krishnan R., Binkley J. S., Seeger R., Pople J. A., J. Chem. Phys., 1980, 72, 650
[28] Badger R. M., Bauer S. H., J. Chem. Phys., 1937, 5, 839
[29] Wong M. W., Chem. Phys. Lett., 1996, 256, 391
[30] Fukui K., Acc. Chem. Res., 1981, 14, 363
[31] Tomasi J., Mennucci B., Cammi R., Chem. Rev., 2005, 105, 2999
[32] Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Scalmani G., Barone V., Petersson G. A., Nakatsuji H., Li X., Caricato M., Marenich A., Bloino J., Janesko B. G., Gomperts R., Mennucci B., Hratchian H. P., Ortiz J. V., Izmaylov A. F., Sonnenberg J. L., Williams-Young D., Ding F., Lipparini F., Egidi F., Goings J., Peng B., Petrone A., Henderson T., Ranasinghe D., Zakrzewski V. G., Gao J., Rega N., Zheng G., Liang W., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Throssell K., Montgomery J. A. Jr., 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., Millam J. M., Klene M., Adamo C., Cammi R., Ochterski J. W., Martin R. L., Morokuma K., Farkas O., Foresman J. B., Fox D. J., Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford, CT, 2016
[33] Sakata K., Fujimoto H., Eur. J. Org. Chem., 2016, 2016, 4275

An Intuitive Electric-field Contribution Decomposition Model for Chemical Processes and Its Applications on Diels-Alder Reactions

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