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Amine adducts of (4-ClC6H4)3B3O3, Lewis acidity of triarylboroxines, and an XRD study on the related tetraphenylboroxinate(1-) salt, [C6H11NMe3][Ph4B3O3]

Amine adducts of (4-ClC6H4)3B3O3, Lewis acidity of triarylboroxines, and an XRD study on the related tetraphenylboroxinate(1-) salt, [C6H11NMe3][Ph4B3O3]
Amine adducts of (4-ClC6H4)3B3O3, Lewis acidity of triarylboroxines, and an XRD study on the related tetraphenylboroxinate(1-) salt, [C6H11NMe3][Ph4B3O3]

The stoichiometric reactions of amines with tri(4-chlorophenyl)boroxine (CPB) led to the formation of adducts CPB·L (L = morpholine (1a), benzylamine (1b) cyclohexylamine (1c), 2-picoline (1d), 4-picoline (1e), piperidine (1f)) and (CPB)2·(4,4'-trimethylenedipiperidine) (1g). Compounds 1a-1g have been characterized by NMR (11B, 1H, 13C), IR spectroscopy and powder-XRD. VT 1H NMR spectra on 1a and 1d-1g were consistent with a ligand exchange/recombination process and activation energies of 49-58 kJ mol-1 were obtained. The synthesis of [C6H11NMe3][Ph4B3O3] (2) from Ph2BOBPh2, PhB(OH)2 and [C6H11NMe3][OH] in a 1:4:2 ratio in MeOH/H2O is also reported. Compound 2 was characterized by thermal analysis (TGA/DSC), spectroscopy (IR, NMR) and 1a, 1b and 2 were further characterized by single-crystal XRD studies.

Boroxine, Tetraphenylboroxinate(1-), Tri(4-chlorophenyl)boroxine, Triarylboroxine, VT NMR, XRD structures
0022-328X
Beckett, Michael A.
5b021ef6-fa5c-4f6d-9998-3313558f0dc1
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Jones, Charlotte L.
d21b38a5-f7df-4ffd-8a7e-de716b1aeaeb
Marshall, Elizabeth V.
705bc9cb-88ed-428c-89f5-f88ace55f2d9
Perry, Thomas
68eefc5c-8d58-4770-8cb5-09d19bfb22cd
Beckett, Michael A.
5b021ef6-fa5c-4f6d-9998-3313558f0dc1
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Jones, Charlotte L.
d21b38a5-f7df-4ffd-8a7e-de716b1aeaeb
Marshall, Elizabeth V.
705bc9cb-88ed-428c-89f5-f88ace55f2d9
Perry, Thomas
68eefc5c-8d58-4770-8cb5-09d19bfb22cd

Beckett, Michael A., Coles, Simon J., Horton, Peter N., Jones, Charlotte L., Marshall, Elizabeth V. and Perry, Thomas (2018) Amine adducts of (4-ClC6H4)3B3O3, Lewis acidity of triarylboroxines, and an XRD study on the related tetraphenylboroxinate(1-) salt, [C6H11NMe3][Ph4B3O3]. Journal of Organometallic Chemistry. (doi:10.1016/j.jorganchem.2018.01.012).

Record type: Article

Abstract

The stoichiometric reactions of amines with tri(4-chlorophenyl)boroxine (CPB) led to the formation of adducts CPB·L (L = morpholine (1a), benzylamine (1b) cyclohexylamine (1c), 2-picoline (1d), 4-picoline (1e), piperidine (1f)) and (CPB)2·(4,4'-trimethylenedipiperidine) (1g). Compounds 1a-1g have been characterized by NMR (11B, 1H, 13C), IR spectroscopy and powder-XRD. VT 1H NMR spectra on 1a and 1d-1g were consistent with a ligand exchange/recombination process and activation energies of 49-58 kJ mol-1 were obtained. The synthesis of [C6H11NMe3][Ph4B3O3] (2) from Ph2BOBPh2, PhB(OH)2 and [C6H11NMe3][OH] in a 1:4:2 ratio in MeOH/H2O is also reported. Compound 2 was characterized by thermal analysis (TGA/DSC), spectroscopy (IR, NMR) and 1a, 1b and 2 were further characterized by single-crystal XRD studies.

Text 1-s2.0-S0022328X18300123-main - Accepted Manuscript
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Accepted/In Press date: 10 January 2018
e-pub ahead of print date: 11 January 2018
Keywords: Boroxine, Tetraphenylboroxinate(1-), Tri(4-chlorophenyl)boroxine, Triarylboroxine, VT NMR, XRD structures

Identifiers

Local EPrints ID: 417426
URI: https://eprints.soton.ac.uk/id/eprint/417426
ISSN: 0022-328X
PURE UUID: d906b6d5-752f-412e-a048-d54c40ca5c3d
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Peter N. Horton: ORCID iD orcid.org/0000-0001-8886-2016

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Date deposited: 31 Jan 2018 17:30
Last modified: 31 Jan 2018 17:30

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Contributors

Author: Michael A. Beckett
Author: Simon J. Coles ORCID iD
Author: Peter N. Horton ORCID iD
Author: Charlotte L. Jones
Author: Elizabeth V. Marshall
Author: Thomas Perry

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