Effect of the silicon atom on the electron density distribution in the organosilicon 1,2-hydroxyamines molecules

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

In the framework of the theory of MO LCAO by the TPSS / cc-pVTZ, Hirshfield and NBO analysis methods in the molecules of 4-(dimethylamino)-1,1-diethylsilacyclopentan-3-ol and 2-(dimethylamino)- 5-trimethylsilylcyclohexan-1-ol the nature of the influence of the silicon atom on remotely located nitrogen and oxygen atoms has been studied. More pronounced in 4-(dimethylamino)-1,1-diethylsilacyclopentan-3-ol molecule, this effect is determined by the geometric parameters (endocyclic arrangement of the silicon atom), which favor the formation of MOs with a large Si contribution. According to NBO analysis, the interaction between the orbitals of the Si-C5 bonds and the orbitals of the C3-N and C1-O bonds in the silacyclopentane fragment of the 4-(dimethylamino)-1,1-diethylsilacyclopentan-3-ol molecule, has a donor-acceptor character. The calculated data are in qualitative agreement with the results of 1H and 29Si NMR spectroscopy.

About the authors

E. M. Khamitov

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

I. G. Konkina

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

Email: irkonk@anrb.ru

E. M. Tsyrlina

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

A. N. Lobov

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

S. P. Ivanov

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

References

  1. Rendler S., Oestreich M. // Synthesis. 2005. Vol. 2005. P. 1727. doi: 10.1055/s-2005-869949
  2. Hwang S.-W., Tao H., Kim D.-H., Cheng H., Song J.-K., Rill E., Brenckle M.A., Panilaitis B., Won S.M., Kim Y.-S., Song Y.S., Yu K.J., Ameen A., Li R., Su Y., Yang M., Kaplan D.L., Zakin M.R., Slepian M.J., Huang Y., Omenetto F.G., Rogers J.A. // Science. 2012. Vol. 337. N 6102. P. 1640. doi: 10.1126/science.1226325
  3. Vale J.R., Valkonen A., Afonsom C.A.M., Candeias N.R. // Org. Chem. Front. 2019. Vol. 6. P. 3793. doi: 10.1039/c9qo01028a
  4. Barraza S. J., Denmark S. E. // J. Am. Chem. Soc. 2018. Vol. 140. P. 6668. doi: 10.1021/jacs.8b03187
  5. Pan T.-T., Guo M., Lu P., Hu D. // J. Sci. Food Agric. 2022. Vol. 102. P. 7405. doi: 10.1002/jsfa.12109
  6. Безручко Е.С., Федотова Л.С. // Агрохимия. 2021. № 8. С. 70. doi: 10.31857/S0002188121080032
  7. Даин И.А., Логинов С.В., Рыбаков В.Г., Чернышев В.В., Лебедев А.В., Офицеров Е.Н., Стороженко П.А. // Бутлеровск. сообщ. 2019. Т. 53. № 1. С. 107.
  8. Picard J.-P. // Adv. Organomet. Chem. 2004. Vol. 52. P. 175. doi: 10.1016/S0065-3055(04)52004-X
  9. Tandura S.N., Voronkov M.G., Alekseev N.V. // Top. Curr. Chem. Vol. 131. P. 99. Heidelberg
  10. Berlin: Springer, 1986. doi: 10.1007/3-540-15811-1_3
  11. Singh G., Kaur G., Singh J. // Inorg. Chem. Commun. 2018. Vol. 88. P. 11. doi: 10.1016/j.inoche.2017.12.002
  12. Воронков М. Г., Пестунович В.А., Чернов Н.Ф., Албанов А.И., Белоголова Е.Ф., Клюба Л.В., Пестунович А.Е. // ЖОХ. 2006. Т. 76. № 10. С. 1621
  13. Voronkov M.G., Pestunovich V.A., Chernov N.F., Albanov A.I., Belogolova E.F., Klyba L.V., Pestunovich A.E. // Russ. J. Gen. Chem. 2006. Vol. 76. P. 1554. doi: 10.1134/S1070363206100082
  14. Воронков М.Г., Трофимова О.М., Болгова Ю.И., Чернов Н.Ф. // Усп. хим. 2007. Т. 76. № 9. С. 885
  15. Voronkov M.G., Trofimova O.M., Bolgova Yu.I., Chernov N.F. // Russ. Chem. Rev. 2007. Vol. 76. N 9. P. 825. doi: 10.1070/RC2007v076n09ABEH003706
  16. Шелудяков В.Д., Кузьмина Н.Е., Абрамкин А.Н., Корлюков А.А., Архипов Д.Е., Логинов С.В., Чешков Д.А., Стороженко П.А. // ЖОХ. 2011. Т. 81. № 12. С. 2010
  17. Sheludyakov V.D., Kuz'mina N.E., Abramkin A.M., Korlyukov A.A., Arkhipov D.E., Loginov S.V., Cheshkov D.A., Storozhenko P.A. // Russ. J. Gen. Chem. 2011. Vol. 81. N 12. P. 2468. doi: 10.1134/S1070363211120085
  18. Lyssenko K.A., Korlyukov A.A., Antipin M.Y., Knyazev S.P., Kirin V N., Alexeev N.V., Chernyshev E.A. // Mendeleev Commun. 2000. Vol. 10. N 3. P. 88. doi: 10.1070/MC2000v010n03ABEH001270
  19. Belogolova E.F., SidorkinV.F. // Mol. Struct. Theochem. 2004. Vol. 668. N 2-3. P. 139. doi: 10.1016/j.theochem.2003.10.020
  20. Trofimov A.B., Zakrzewski V.G., Dolgounitcheva O., Ortiz J.V., Sidorkin V.F., Belogolova E.F., Belogolov M., Pestunovich V.A. // J. Am. Chem. Soc. 2005. Vol. 127. N 3. P. 986. doi 1021/ja045667q
  21. Sidorkin V.F., Belogolova E.F., Doronina E.P. // Phys. Chem. Chem. Phys. 2015. Vol. 17. N 39. P. 26225. doi: 10.1039/c5cp04341g PMID: 26381586.
  22. Корлюков А.А. // Усп. хим. 2015. Т. 84. № 4. С. 422
  23. Korlyukov A. A. // Russ. Chem. Rev. 2015. Vol. 84. N 4. P. 422. doi: 10.1070/RCR4466
  24. Sterkhova I.V., Lazareva N.F. // SSRN. Abstract 4368146. doi: 10.2139/ssrn.4368146
  25. Lazareva N.F., Alekseev M.A., Sterkhova I.V. // Mendeleev Commun. 2022. Vol. 32. N 5. P. 686. doi: 10.1016/j.mencom.2022.09.040
  26. Цырлина Е.М. Дис. канд. хим. наук. Уфа, 1985. 187 с.
  27. Конкина И.Г., Муринов Ю.И. // Вестн. БашГУ. 2021. Т. 26. № 1. С. 47. doi: 10.33184/bulletin-bsu-2021.1.8
  28. Krapivin A.M., Magi M., Svergun V.I., Zaharjan R.Z., Babich E.D., Ushakov N.V. // J. Organomet. Chem.1980. Vol. 190. N 1. P. 9. doi: 10.1016/S0022-328X(00)82875-2
  29. Frieman F., Fang C., Shainyan B.A. // Int. J. Quant. Chem. 2004. Vol. 100. P. 720. doi: 10.1002/qua.20236
  30. Гайлюнас И.А., Цырлина Е.М., Соловьева Н.И., Комаленкова Н.Г., Юрьев Е.П. // ЖОХ. 1977. Т. 47. № 10. С. 2394.
  31. Тюрина Л.А., Гайлюнас И.А., Семенов В.А., Цырлина Е.М., Сингизова В.Х., Соловьева В.И. // ЖОХ. 1981. Т. 51. № 12. С. 2691.
  32. Kiss-Eröss K., Svehla G. Analytical Infrared Spectroscopy. Amsterdam; Oxford; New York: Elsevier Scientific Publishing Company, 1976.
  33. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., ScalmaniG., 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., Montgomery J.A., Jr., Peralta J.E., Ogliaro F., Bearpark M., Heyd J.J., Brothers E., Kudin K.N., Staroverov V.N., 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., Bakke V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E. Yazyev O., Austin A.J., Cammi R., Pomell C., Ochterski J.W., Martin R.L., Morokum K., Zakrzewski V.G., Vot G.A., Salvado P., Dannenberg J.J., Dapprich S., Daniels A.D., Farkas Ö., Foresman J.B., Ortiz J.V., Cioslowski J., Fox D.J. Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford CT, 2009.
  34. Tao J., Perdew J.P., Staroverov V.N., Scuseria G.E. // Phys. Rev. Lett. 2003. Vol. 91. N 14. Article 146401. doi: 10.1103/PhysRevLett.91.146401
  35. Woon D. E., Dunning T. H. // J. Chem. Phys. 1993. Vol. 98. P. 1358. doi: 10.1063/1.464303
  36. Lu T., Manzetti S. // Struct. Chem. 2014. Vol. 25. P. 1521. doi: 10.1007/s11224-014-0430-6
  37. Lu T., Chen F. // J. Comput. Chem. 2012. Vol. 33. P. 580. doi: 10.1002/jcc.22885
  38. Humphrey W., Dalke A., Schulten K. // J. Mol. Graph. 1996. Vol. 14. P. 33. doi: 10.1016/0263-7855(96)00018-5
  39. Chemcraft. https://www.chemcraftprog.com
  40. Emamian S., Lu T., Kruse H., Emamian H. // J. Comput. Chem. 2019. Vol. 40. P. 2868. doi: 10.1002/jcc.26068
  41. Reed A.E., Weinhold F. // J. Chem. Phys. 1985. Vol. 83. P. 1736. doi.org/10.1063/1.449360

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2023 Russian Academy of Sciences