Keywords
N-isopropyl-N',N'-dimethyl-N-(silylmethyl)ureas
fluorosilanes
NMR
organosilicon compounds
pentacoordinate silicon
X-ray diffraction analysis
Abstract
Novel N-isopropyl-N',N'-dimethyl-N-(silylmethyl)ureas Me2NC(O)N(Pri)CH2SiMenX3–n (X = OEt, F; n = 0–2) were synthesized, and their structure was confirmed by 1H, 13C and 29Si NMR spectroscopy. According to NMR data, the silicon atom of the fluorosilanes (X = F) is pentacoordinated. The X-ray diffraction analysis of the (trifluorosilyl)methylcontaining urea showed that it exists as (O–Si) chelate with intramolecular dative bond C=O→Si (1.880 Å).
References
1.
10.1016/j.mencom.2022.09.040_b0005
Voronkov
Organomet. Chem. USSR,
1991
2.
Chuit C., Corriu R.J., Reye C., Young J.C.
Chemical Reviews,
1993
3.
10.1016/j.mencom.2022.09.040_b0015
Negrebetsky
Russ. Chem. Bull.,
1807
4.
10.1016/j.mencom.2022.09.040_b0020
The Chemistry of Organic Silicon Compounds,
1998
5.
Nikolin A.A., Negrebetsky V.V.
Russian Chemical Reviews,
2014
6.
Korlyukov A.A.
Russian Chemical Reviews,
2015
7.
Volz N., Clayden J.
Angewandte Chemie - International Edition,
2011
8.
Delebecq E., Pascault J., Boutevin B., Ganachaud F.
Chemical Reviews,
2012
9.
Dydio P., Lichosyt D., Jurczak J.
Chemical Society Reviews,
2011
10.
Kalistratova A.V., Kovalenko L.V., Oshchepkov M.S., Gamisoniya A.M., Gerasimova T.S., Demidov Y.A., Akimov M.G.
Mendeleev Communications,
2020
11.
Voronkov M.G., Pestunovich A.E., Albanov A.I., Vlasova N.N., Pestunovich V.A.
Russian Chemical Bulletin,
1989
12.
10.1016/j.mencom.2022.09.040_b0060
Pudovik
Russ. J. Gen. Chem.,
2000
13.
Bassindale A.
Journal of Organometallic Chemistry,
2001
14.
Pudovik M.A., Kibardina L.K., Pudovik A.N.
Russian Journal of General Chemistry,
2004
15.
Hwu J.R., King K.Y.
Chemistry - A European Journal,
2005
16.
10.1016/j.mencom.2022.09.040_b0080
Sidorkin
Chem. – Eur. J.,
2021
17.
Rauf W., Brown J.
Angewandte Chemie - International Edition,
2008
18.
Mizumo T., Muragishi H., Yamamoto K., Ohshita J., Kanezashi M., Tsuru T.
Applied Organometallic Chemistry,
2015
19.
Barraza S.J., Denmark S.E.
Journal of the American Chemical Society,
2018
20.
Zhang X., Geng P., Liu G., Huang Z.
Organometallics,
2021
21.
Synthesis and structure of potentially biologically active N-(silylmethyl)tetrahydropyrimidin-2-ones
Lazareva N.F., Lazarev I.M.
Russian Chemical Bulletin,
2014
22.
Pestunovich V.A., Albanov A.I., Pogozhikh S.A., Ovchinnikov Y.E., Lazareva N.F.
Journal of Molecular Structure,
2012
23.
Lazareva N.F., Sterkhova I.V., Albanov A.I.
Journal of Organometallic Chemistry,
2018
24.
Chipanina N.N., Lazareva N.F., Aksamentova T.N., Nikonov A.Y., Shainyan B.A.
Organometallics,
2014
25.
10.1016/j.mencom.2022.09.040_b0125
Luo
Comprehensive Handbook of Chemical Bond Energies,
2007
26.
10.1016/j.mencom.2022.09.040_b0130
Voronkov
Organomet. Chem. USSR,
1992
27.
Soldatenko A.S., Sterkhova I.V., Lazareva N.F.
Russian Chemical Bulletin,
2022
28.
Lazareva N.F., Sterkhova I.V., Vashchenko A.V.
Journal of Molecular Structure,
2021
29.
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography,
2007
30.
Soldatenko A.S., Sterkhova I.V., Lazareva N.F.
Journal of Organometallic Chemistry,
2021
31.
Ovchinnikov Y.E., Mozzhukhin A.O., Antipin M.Y., Struchkov Y.T., Baryshok V.P., Lazareva N.F., Voronkov M.G.
Journal of Structural Chemistry,
1994