Quantum-chemical study of the structure of amidinyltetramethoxycarbonylcyclopentadiene and its Hg(II) and Tl(I) complexes
- 作者: Dushenko G.1, Mikhailov I.1, Mikhailova O.1, Minyaev R.1, Minkin V.1
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隶属关系:
- Institute of Physical and Organic Chemistry of Southern Federal University
- 期: 卷 93, 编号 4 (2023)
- 页面: 610-621
- 栏目: Articles
- URL: https://journals.rcsi.science/0044-460X/article/view/145024
- DOI: https://doi.org/10.31857/S0044460X23040133
- EDN: https://elibrary.ru/AVQROK
- ID: 145024
如何引用文章
详细
DFT CAM-B3LYP/6-311++G(d,p) and CAM-B3LYP/6-311++G(d,p)/SDD calculations showed that the polydentate amidinyltetramethoxycarbonylcyclopentadienyl ligand and its Hg(II) and Tl(I) complexes are the most stable in the form of ylide isomers, in which the hydrogen or metal atom is bonded to the terminal nitrogen atom of the amidinium fragment and in the case of metal complexes, it is additionally coordinated by the π -system of the cyclopentadiene ring. Alternative isomers in which hydrogen or metal atoms are bonded to carbon atoms of the cyclopentadiene ring or to carbonyl oxygen atoms of methoxycarbonyl substituents are energetically less stable at Δ E ZPE = 4.1-15.1 kcal/mol.
作者简介
G. Dushenko
Institute of Physical and Organic Chemistry of Southern Federal University
Email: gadushenko@sfedu.ru
I. Mikhailov
Institute of Physical and Organic Chemistry of Southern Federal University
O. Mikhailova
Institute of Physical and Organic Chemistry of Southern Federal University
R. Minyaev
Institute of Physical and Organic Chemistry of Southern Federal University
V. Minkin
Institute of Physical and Organic Chemistry of Southern Federal University
参考
- Михайлов И.Е., Душенко Г.А., Минкин В.И. // ЖОрХ. 2021. Т. 57. Вып. 11. С. 1505
- Mikhailov I.E., Dushenko G.A., Minkin V.I. // Russ. J. Org. Chem. 2021. Vol. 57. N 11. P. 1757. doi: 10.1134/S1070428021110014
- Gheewala C.D., Collins B.E., Lambert T.H. // Science. 2016. Vol. 351. P. 961. doi: 10.1126/science.aad0591
- Gheewala C.D., Radtke M.A., Hui J., Hon A.B., Lambert T.H. // Org. Lett. 2017. Vol. 19. P. 4227. doi: 10.1021/acs.orglett.7b01867
- Gheewala C.D., Hirschi J.S., Lee W.-H., Paley D.W., Vetticatt M.J., Lambert T.H. // J. Am. Chem. Soc. 2018. Vol. 140. P. 3523. doi: 10.1021/jacs.8b00260
- Salikov R.F., Trainov K.P., Platonov D.N., Davydov D.A., Lee S., Gerasimov I.S., Medvedev M.G., Levina A.A., Belyy A.Yu., Tomilov Yu.V. // Dyes Pigments. 2019. Vol. 161. P. 500. doi: 10.1016/j.dyepig.2018.09.040
- Trainov K.P., Salikov R.F., Platonov D.N., Tomilov Yu.V. // Mendeleev Commun. 2020. Vol. 30. P. 647. doi: 10.1016/j.mencom.2020.09.032
- Jayanty S., Kumar D.B.K., Radhakrishnan T.P. // Synth. Met. 2000. Vol. 114. P. 37. doi: 10.1016/S0379-6779(00)00204-6
- Griffin P.J., Freyer J.L., Han N., Geller N., Yin X., Gheewala C.D., Lambert T.H., Campos L.M., Winey K.I. // Macromolecules. 2018. Vol. 51. P. 1681. doi: 10.1021/acs.macromol.7b02546
- Jayanty S., Radhakrishnan T.P. // J. Mater. Chem. 1999. Vol. 9. P. 1707. doi: 10.1039/a901661i
- Müller C., Vos D., Jutzi P. // J. Organomet. Chem. 2000. Vol. 600. P. 127. doi: 10.1016/S0022-328X(00)00060-7
- Moxey G.J., Ortu F., Sidley L.G., Strandberg H.N., Blake A.J., Lewis W., Kays D.L. // Dalton Trans. 2014. Vol. 43. P. 4838. doi: 10.1039/c3dt53234h
- Kalz K.F., Hausmann A., Dechert S., Meyer S., John M., Meyer F. // Chem. Eur. J. 2016. Vol. 22. P. 18190. doi: 10.1002/chem.201603850
- Минкин В.И., Михайлов И.Е., Душенко Г.А., Жунке А. // Усп. хим. 2003. Т. 72. № 10. С. 978
- Minkin V.I., Mikhailov I.E., Dushenko G.A., Zschunke A. // Russ. Chem. Rev. 2003. Vol. 72. N 10. P. 867. doi: 10.1070/RC2003v072n10ABEH000848
- Morsalia A., Masoomi M.Y. // Coord. Chem. Rev. 2009. Vol. 253. P. 1882. doi: 10.1016/j.ccr.2009.02.018
- Wong W.-Y. // Coord. Chem. Rev. 2007. Vol. 251. P. 2400. doi: 10.1016/j.ccr.2007.01.006
- Beheshti A., Mousavifard E.S., Kubicki M., Grześkiewicz A., Rezatofighi S.E. // Inorg. Chim. Acta. 2021. Vol. 514. P. 120010. doi: 10.1016/j.ica.2020.120010
- Janiak C. // Coord. Chem. Rev. 1997. Vol. 163. P. 107. doi: 10.1016/S0010-8545(97)00011-8
- Blockhaus T., Sunkel K. // Z. anorg. allg. Chem. 2021. Vol. 647. P. 1849. doi: 10.1002/zaac.202100244
- Dushenko G.A., Mikhailov I.E., Kompan O.E., Zschunke A., Reck G., Schulz B., Mugge C., Minkin V.I. // Mendeleev Commun. 1997. Vol. 7. N 4. P. 127. doi: 10.1070/MC1997v007n04ABEH000761
- Душенко Г.А., Михайлов И.Е., Reck G., Schulz B., Zschunke A., Харабаев Н.Н., Минкин В.И. // ЖОрХ. 2002. Т. 38. Вып. 7. С. 1024
- Dushenko G.A., Mikhailov I.E., Reck G., Schulz B., Zschunke A., Kharabaev N.N., Minkin V.I. // Russ. J. Org. Chem. 2002. Vol. 38. N 7. P. 982. doi: 10.1023/A:1020897411534
- Mikhailov I.E., Kompan O.E., Dushenko G.A., Minkin V.I. // Mendeleev Commun. 1991. Vol. 1. N 4. P. 121. doi: 10.1070/MC1991v001n04ABEH000074
- Minkin V.I., Mikhailov I.E., Dushenko G.A. // J. Chem. Soc. Chem. Commun. 1988. N 17. P. 1181. doi: 10.1039/C39880001181
- Душенко Г.А., Михайлов И.Е., Reck G., Schulz B., Zschunke A., Минкин В.И. // Изв. АН. Сер. xим. 2001. Т. 50. № 5. С. 852
- Dushenko G.A., Mikhailov I.E., Reck G., Schulz B., Zschunke A., Minkin V.I. // Russ. Chem. Bull. 2001. Vol. 50. N 5. P. 890. doi: 10.1023/A:1011323629390
- Bruce M.I., White A.H. // Aust. J. Chem. 1990. Vol. 43. P. 949. doi: 10.1071/CH9900949
- Lei Y.X., Cerioni G., Rappoport Z. // J. Org. Chem. 2000. Vol. 65. P. 4028. doi: 10.1021/jo000046a
- Душенко Г.А., Михайлов И.Е., Михайлова О.И., Миняев Р.М., Минкин В.И. // Докл. АН. 2017. Т. 476. С. 648
- Dushenko G.A., Mikhailov I.E., Mikhailova O.I., Minyaev R.M., Minkin V.I. // Dokl. Chem. 2017. Vol. 476. P. 230. doi: 10.1134/S0012500817100020
- Schulte Y., Weinert H., Wolper C., Schulz S. // Organometallics. 2020. Vol. 39. P. 206. doi: 10.1021/acs.organomet.9b00741
- Sitzmann H., Wolmershäuser G. // Z. anorg. Allg. Chem. 1995. Vol. 621. P. 109. doi: 10.1002/zaac.19956210120
- Razavi A., Rausch M.D., Alt H.G. // J. Organomet. Chem. 1987. Vol. 329. P. 281. doi: 10.1016/0022-328X(87)80061-X
- Wulfsberg G.P., Frye J.S., Buchanan A.C., Weiss A., Jui C.C.C., Davis D.A., Bass K., Todd R.W. // Organometallics. 1987. Vol. 6. P. 2363. doi: 10.1021/om00154a016
- Weiden N., Weiss A., Wulfsberg G., Ilsley W., Benner K., Wourster W. // Zeit. Naturforsch. (A). 1990. Vol. 45. P. 503. doi: 10.1515/zna-1990-3-450
- Душенко Г.А., Михайлов И.Е., Михайлова О.И., Миняев Р.М., Минкин В.И. // Докл. АН. 2018. Т. 482. С. 292
- Dushenko G.A., Mikhailov I.E., Mikhailova O.I., Minyaev R.M., Minkin V.I. // Dokl. Chem. 2018. Vol. 482. P. 189. doi: 10.1134/S0012500818090069.
- Dushenko G.A., Mikhailov I.E., Zschunke A., Reck G., Schulz B., Mugge C., Minkin V.I. // Mendeleev Commun. 1999. Vol. 9. N 2. P. 67. doi: 10.1070/mc1999v009n02abeh001064
- Душенко Г.А., Михайлов И.Е., Михайлова О.И., Миняев Р.М., Минкин В.И. // Изв. АН. Сер. xим. 2022. Т. 71. № 9. С. 1847
- Dushenko G.A., Mikhailov I.E., Mikhailova O.I., Minyaev R.M., Minkin V.I. // Russ. Chem. Bull. 2022. Vol. 71. N 9. P. 1847. doi: 10.1007/s11172-022-3601-4
- Михайлов И.Е., Душенко Г.А., Минкин В.И. // Докл. АН. 2007. Т. 412. С. 645
- Mikhailov I.E., Dushenko G.A., Reck G., Schulz B., Zschunke A., Minkin V.I. // Dokl. Chem. 2007. Vol. 412. P. 49. doi: 10.1134/S0012500807020073
- Foresman J.B., Frisch E., Exploring Chemistry with Electronic Structure Methods, Pittsburg: Gaussian Inc., 1996. 302 p.
- 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., 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., 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 E.01. Wallingford CT: Gaussian, Inc. 2013.