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Synthesis and characterization of a tertiary amine:boric acid (1:1) co-crystal and a neutral zwitterionic diamine pentaboron adduct

Synthesis and characterization of a tertiary amine:boric acid (1:1) co-crystal and a neutral zwitterionic diamine pentaboron adduct
Synthesis and characterization of a tertiary amine:boric acid (1:1) co-crystal and a neutral zwitterionic diamine pentaboron adduct

The syntheses of the 4,4′-trimethylenebis(N-methylpiperidine):boric acid (1:1) co-crystal, 4,4′-(1-MeNC5H9)2(CH2)3.B(OH)3 (1), and a zwitterionic tetrahydroxidohexaoxidopentaboron adduct, [B5O6(OH)4(κN-NH2CH2CH2NHEt2).H2O (2), (NH2CH2CH2NEt2 = deen) from appropriate combinatorial libraries primed with B(OH)3, are reported together with their spectroscopic (NMR, IR) and single-crystal XRD characterization data. Solid-state H-bond interactions are the likely strong drivers for their formation, and these are described in detail. H-bond networks present in co-crystal 1 include C22(16), R22(8), and R66(36) whilst zwitterionic pentaboron derivative 2 has three R22(8) intermolecular H-bond interactions and the Et2NH- group is involved in a S(7) intramolecular H-bond. Thermal (TGA/DSC) data are also reported for 1 which thermally decomposes to B2O3, in a multistage process: dehydration (60–70 °C) and oxidation and further dehydration (90–700 °C).

Boric acid, Co-crystallization, H-bonding, Oxidoboron, Self-assembly, Templated synthesis, XRD, Zwitterion
0020-1693
Altahan, Mohammed A.
a333d79b-2ef3-4c3f-86a2-519740d08a72
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
Altahan, Mohammed A.
a333d79b-2ef3-4c3f-86a2-519740d08a72
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

Altahan, Mohammed A., Beckett, Michael A., Coles, Simon J., Horton, Peter N. and Jones, Charlotte L. (2022) Synthesis and characterization of a tertiary amine:boric acid (1:1) co-crystal and a neutral zwitterionic diamine pentaboron adduct. Inorganica Chimica Acta, 539, [120998]. (doi:10.1016/j.ica.2022.120998).

Record type: Article

Abstract

The syntheses of the 4,4′-trimethylenebis(N-methylpiperidine):boric acid (1:1) co-crystal, 4,4′-(1-MeNC5H9)2(CH2)3.B(OH)3 (1), and a zwitterionic tetrahydroxidohexaoxidopentaboron adduct, [B5O6(OH)4(κN-NH2CH2CH2NHEt2).H2O (2), (NH2CH2CH2NEt2 = deen) from appropriate combinatorial libraries primed with B(OH)3, are reported together with their spectroscopic (NMR, IR) and single-crystal XRD characterization data. Solid-state H-bond interactions are the likely strong drivers for their formation, and these are described in detail. H-bond networks present in co-crystal 1 include C22(16), R22(8), and R66(36) whilst zwitterionic pentaboron derivative 2 has three R22(8) intermolecular H-bond interactions and the Et2NH- group is involved in a S(7) intramolecular H-bond. Thermal (TGA/DSC) data are also reported for 1 which thermally decomposes to B2O3, in a multistage process: dehydration (60–70 °C) and oxidation and further dehydration (90–700 °C).

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Accepted/In Press date: 28 April 2022
e-pub ahead of print date: 2 May 2022
Published date: 1 September 2022
Additional Information: Funding Information: We thank the EPSRC for the NCS X-ray crystallographic service (Southampton). Publisher Copyright: © 2022 The Authors Copyright: Copyright 2022 Elsevier B.V., All rights reserved.
Keywords: Boric acid, Co-crystallization, H-bonding, Oxidoboron, Self-assembly, Templated synthesis, XRD, Zwitterion

Identifiers

Local EPrints ID: 458047
URI: http://eprints.soton.ac.uk/id/eprint/458047
ISSN: 0020-1693
PURE UUID: 825c635b-d752-4294-93a1-5ef457eee36e
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: 27 Jun 2022 17:08
Last modified: 28 Jun 2022 01:37

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Contributors

Author: Mohammed A. Altahan
Author: Michael A. Beckett
Author: Simon J. Coles ORCID iD
Author: Peter N. Horton ORCID iD
Author: Charlotte L. Jones

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