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Triorganoantimony(V) complexes with internally functionallized oximes: synthetic, spectroscopic and structural aspects of [R3Sb(Br)L], [R3Sb(OH)L] and [R3SbL2], crystal and molecular structures of [Me3Sb{ON=C(Me)C4H3O}2], [Me3Sb{ON=C(Me)C4H3S}2], 2-OC4H3C(Me)=NOH and 2-SC4H3C(Me)=NOH

Triorganoantimony(V) complexes with internally functionallized oximes: synthetic, spectroscopic and structural aspects of [R3Sb(Br)L], [R3Sb(OH)L] and [R3SbL2], crystal and molecular structures of [Me3Sb{ON=C(Me)C4H3O}2], [Me3Sb{ON=C(Me)C4H3S}2], 2-OC4H3C(Me)=NOH and 2-SC4H3C(Me)=NOH
Triorganoantimony(V) complexes with internally functionallized oximes: synthetic, spectroscopic and structural aspects of [R3Sb(Br)L], [R3Sb(OH)L] and [R3SbL2], crystal and molecular structures of [Me3Sb{ON=C(Me)C4H3O}2], [Me3Sb{ON=C(Me)C4H3S}2], 2-OC4H3C(Me)=NOH and 2-SC4H3C(Me)=NOH
Triorganoantimony(V) complexes with internally functionallized oximes of the type [R3Sb{ON=C(Me)Ar}2] (1) [R=Me, Pri; Ar=C5H4N, C4H3S, C4H3O] have been prepared by the reaction of R3SbBr2 with the corresponding oximes in 1:2 molar ratio in anhydrous benzene. Treatment of 1 with one equivalent of R3SbX2 afforded a redistribution product [R3Sb(X){ON=C(Me)Ar}] (2) [X=(a):Br, (b):OH]. The species, R3Sb(OH)L, may also be obtained by the controlled hydrolysis of 1 (R=Pri; Ar=C5H4N). All of these complexes have been characterized by elemental analyses, and IR and NMR (1H and 13C) spectroscopic studies. Crystal structures of [Me3Sb{ON=C(Me)C4H3O-2}2] (3), [Me3Sb{ON=C(Me)C4H3S-2}2] (4) 2-OC4H3C(Me)=NOH (5) and 2-SC4H3C(Me)=NOH (6) are reported. The geometry around the antimony atom in 3 and 4 is distorted trigonal bipyramidal with the carbon atoms of the SbMe3 unit in equatorial positions and the two oxygen atoms of the oxime group occupying axial positions (O(1)---Sb---O(2) 171.67(12) in 3 and 169.14(13) in 4). The free oxime is clearly hydrogen bonded (H---N 2.08 Å in 6) to essentially form a dimer.
trialkylantimony(v), oximes, nmr, x-ray, antitumor properties, organic derivatives, spectra, chemistry, bismuth
0022-328X
118-126
Gupta, Anjali
21d25dce-1320-4d3a-9174-3ce1b76ed228
Sharma, Rajnish K.
ca082c38-d6dc-4913-9c4a-a02c8c2f7c7b
Bohra, Rakesh
992e54e6-6f5d-47f1-8ddc-121dc0d1f796
Jain, Vimal K.
015a82e5-71eb-4107-8f06-7bffeb602553
Drake, John E.
6de1350f-4eb6-4ca7-b796-947f4fec467d
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Gupta, Anjali
21d25dce-1320-4d3a-9174-3ce1b76ed228
Sharma, Rajnish K.
ca082c38-d6dc-4913-9c4a-a02c8c2f7c7b
Bohra, Rakesh
992e54e6-6f5d-47f1-8ddc-121dc0d1f796
Jain, Vimal K.
015a82e5-71eb-4107-8f06-7bffeb602553
Drake, John E.
6de1350f-4eb6-4ca7-b796-947f4fec467d
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161

Gupta, Anjali, Sharma, Rajnish K., Bohra, Rakesh, Jain, Vimal K., Drake, John E., Hursthouse, Michael B. and Light, Mark E. (2002) Triorganoantimony(V) complexes with internally functionallized oximes: synthetic, spectroscopic and structural aspects of [R3Sb(Br)L], [R3Sb(OH)L] and [R3SbL2], crystal and molecular structures of [Me3Sb{ON=C(Me)C4H3O}2], [Me3Sb{ON=C(Me)C4H3S}2], 2-OC4H3C(Me)=NOH and 2-SC4H3C(Me)=NOH. Journal of Organometallic Chemistry, 645 (1-2), 118-126. (doi:10.1016/S0022-328X(01)01338-9).

Record type: Article

Abstract

Triorganoantimony(V) complexes with internally functionallized oximes of the type [R3Sb{ON=C(Me)Ar}2] (1) [R=Me, Pri; Ar=C5H4N, C4H3S, C4H3O] have been prepared by the reaction of R3SbBr2 with the corresponding oximes in 1:2 molar ratio in anhydrous benzene. Treatment of 1 with one equivalent of R3SbX2 afforded a redistribution product [R3Sb(X){ON=C(Me)Ar}] (2) [X=(a):Br, (b):OH]. The species, R3Sb(OH)L, may also be obtained by the controlled hydrolysis of 1 (R=Pri; Ar=C5H4N). All of these complexes have been characterized by elemental analyses, and IR and NMR (1H and 13C) spectroscopic studies. Crystal structures of [Me3Sb{ON=C(Me)C4H3O-2}2] (3), [Me3Sb{ON=C(Me)C4H3S-2}2] (4) 2-OC4H3C(Me)=NOH (5) and 2-SC4H3C(Me)=NOH (6) are reported. The geometry around the antimony atom in 3 and 4 is distorted trigonal bipyramidal with the carbon atoms of the SbMe3 unit in equatorial positions and the two oxygen atoms of the oxime group occupying axial positions (O(1)---Sb---O(2) 171.67(12) in 3 and 169.14(13) in 4). The free oxime is clearly hydrogen bonded (H---N 2.08 Å in 6) to essentially form a dimer.

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Published date: 15 February 2002
Keywords: trialkylantimony(v), oximes, nmr, x-ray, antitumor properties, organic derivatives, spectra, chemistry, bismuth

Identifiers

Local EPrints ID: 19750
URI: http://eprints.soton.ac.uk/id/eprint/19750
ISSN: 0022-328X
PURE UUID: 4631a94c-0826-4fda-8387-0755c2ec752d
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 20 Feb 2006
Last modified: 09 Jan 2022 02:59

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Contributors

Author: Anjali Gupta
Author: Rajnish K. Sharma
Author: Rakesh Bohra
Author: Vimal K. Jain
Author: John E. Drake
Author: Mark E. Light ORCID iD

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