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Chiral anionic layers in tartramide spiroborate salts and variable solvation for [NR4][B(TarNH2)2] (R = Et, Pr or Bu).
Acta Crystallogr C Struct Chem. 2020 Jul 01; 76(Pt 7):695-705.AC

Abstract

The spiroborate anion, namely, 2,3,7,8-tetracarboxamido-1,4,6,9-tetraoxa-5λ4-boraspiro[4.4]nonane, [B(TarNH2)2]-, derived from the diol L-tartramide TarNH2, [CH(O)(CONH2)]2, shows a novel self-assembly into two-dimensional (2D) layer structures in its salts with alkylammonium cations, [NR4]+ (R = Et, Pr and Bu), and sparteinium, [HSpa]+, in which the cations and anions are segregated. The structures of four such salts are reported, namely, the tetrapropylazanium salt, C12H28N+·C8H12BN4O8-, the tetraethylazanium salt hydrate, C8H20N+·C8H12BN4O8-·6.375H2O, the tetrabutylazanium salt as the ethanol monosolvate hemihydrate, C16H36N+·C8H12BN4O8-·C2H5OH·0.5H2O, and the sparteinium (7-aza-15-azoniatetracyclo[7.7.1.02,7.010,15]heptadecane) salt as the ethanol monosolvate, C15H27N2+·C8H12BN4O8-·C2H5OH. The 2D anion layers have preserved intermolecular hydrogen bonding between the amide groups and a typical metric repeat of around 10 × 15 Å. The constraint of matching the interfacial area organizes the cations into quite different solvated arrangements, i.e. the [NEt4] salt is highly hydrated with around 6.5H2O per cation, the [NPr4] salt apparently has a good metric match to the anion layer and is unsolvated, whilst the [NBu4] salt is intermediate and has EtOH and H2O in its cation layer, which is similar to the arrangement for the chiral [HSpa]+ cation. This family of salts shows highly organized chiral space and offers potential for the resolution of both chiral cations and neutral chiral solvent molecules.

Authors+Show Affiliations

Department of Chemistry, Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong, People's Republic of China.Department of Chemistry, Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong, People's Republic of China.Department of Chemistry, Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong, People's Republic of China.Department of Chemistry, Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong, People's Republic of China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32624517

Citation

Soecipto, Aristyo, et al. "Chiral Anionic Layers in Tartramide Spiroborate Salts and Variable Solvation for [NR4][B(TarNH2)2] (R = Et, Pr or Bu)." Acta Crystallographica. Section C, Structural Chemistry, vol. 76, no. Pt 7, 2020, pp. 695-705.
Soecipto A, Wong LWY, Sung HHY, et al. Chiral anionic layers in tartramide spiroborate salts and variable solvation for [NR4][B(TarNH2)2] (R = Et, Pr or Bu). Acta Crystallogr C Struct Chem. 2020;76(Pt 7):695-705.
Soecipto, A., Wong, L. W. Y., Sung, H. H. Y., & Williams, I. D. (2020). Chiral anionic layers in tartramide spiroborate salts and variable solvation for [NR4][B(TarNH2)2] (R = Et, Pr or Bu). Acta Crystallographica. Section C, Structural Chemistry, 76(Pt 7), 695-705. https://doi.org/10.1107/S2053229620008384
Soecipto A, et al. Chiral Anionic Layers in Tartramide Spiroborate Salts and Variable Solvation for [NR4][B(TarNH2)2] (R = Et, Pr or Bu). Acta Crystallogr C Struct Chem. 2020 Jul 1;76(Pt 7):695-705. PubMed PMID: 32624517.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chiral anionic layers in tartramide spiroborate salts and variable solvation for [NR4][B(TarNH2)2] (R = Et, Pr or Bu). AU - Soecipto,Aristyo, AU - Wong,Lawrence W Y, AU - Sung,Herman H Y, AU - Williams,Ian D, Y1 - 2020/06/30/ PY - 2020/01/23/received PY - 2020/06/23/accepted PY - 2020/7/7/entrez KW - chiral segregation KW - crystal structure KW - l-tartramide KW - organic salts KW - spiroborate SP - 695 EP - 705 JF - Acta crystallographica. Section C, Structural chemistry JO - Acta Crystallogr C Struct Chem VL - 76 IS - Pt 7 N2 - The spiroborate anion, namely, 2,3,7,8-tetracarboxamido-1,4,6,9-tetraoxa-5λ4-boraspiro[4.4]nonane, [B(TarNH2)2]-, derived from the diol L-tartramide TarNH2, [CH(O)(CONH2)]2, shows a novel self-assembly into two-dimensional (2D) layer structures in its salts with alkylammonium cations, [NR4]+ (R = Et, Pr and Bu), and sparteinium, [HSpa]+, in which the cations and anions are segregated. The structures of four such salts are reported, namely, the tetrapropylazanium salt, C12H28N+·C8H12BN4O8-, the tetraethylazanium salt hydrate, C8H20N+·C8H12BN4O8-·6.375H2O, the tetrabutylazanium salt as the ethanol monosolvate hemihydrate, C16H36N+·C8H12BN4O8-·C2H5OH·0.5H2O, and the sparteinium (7-aza-15-azoniatetracyclo[7.7.1.02,7.010,15]heptadecane) salt as the ethanol monosolvate, C15H27N2+·C8H12BN4O8-·C2H5OH. The 2D anion layers have preserved intermolecular hydrogen bonding between the amide groups and a typical metric repeat of around 10 × 15 Å. The constraint of matching the interfacial area organizes the cations into quite different solvated arrangements, i.e. the [NEt4] salt is highly hydrated with around 6.5H2O per cation, the [NPr4] salt apparently has a good metric match to the anion layer and is unsolvated, whilst the [NBu4] salt is intermediate and has EtOH and H2O in its cation layer, which is similar to the arrangement for the chiral [HSpa]+ cation. This family of salts shows highly organized chiral space and offers potential for the resolution of both chiral cations and neutral chiral solvent molecules. SN - 2053-2296 UR - https://www.unboundmedicine.com/medline/citation/32624517/Chiral_anionic_layers_in_tartramide_spiroborate_salts_and_variable_solvation_for_[NR4][B(TarNH2)2]_(R_=_Et,_Pr_or_Bu) DB - PRIME DP - Unbound Medicine ER -
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