Synthesis and inclusion properties of boroncalix[3]arene compounds obtained by self‐assembly of 3‐aminophenylboronic acid and salicylaldehyde derivatives

González‐Hernández, Arturo; Serrano‐Melgar, Gloria; Villamil‐Ramos, Raúl; Barba, Víctor

doi:10.1002/hc.21377

Cited by 2 publications

(3 citation statements)

References 65 publications

(119 reference statements)

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“…The carbon signals for aliphatic groups of the heterocyclic ring were observed between δ = 53.5-71.5 ppm. Finally, the 11 B NMR spectra of all the compounds display a single broad signal in the range of δ = 1.9-7.3 ppm, as expected for tetracoordinated boron derivatives [35][36][37][38][39].…”

Section: Spectroscopic Analysissupporting

confidence: 58%

“…EI-MS m/z (%): 219 ([M-H 2 O] + , 52), 161 (55), 147 (32), 97 (35), 57 (67). 1 (39), 114 (12), 95 (15), 69 (23), 57 (15). 1 H NMR (200 MHz, DMSO-d 6 ) δ: 9.53 (1H, s, H-C=O), 8.07 (1H, s, H-2), 7.71 (1H, d, J = 7.6 Hz, H-4), 7.62 (1H, d, J = 7.4 Hz, H-6), 7.29 (1H, t, J = 7.6 Hz, H-5), 4.31 (4H, AB, J = 10.7 Hz, H-7, H-9), 1.07 (1H, s, H-10).…”

Section: General Methods For the Preparation Of Heterocyclic Boronate...mentioning

confidence: 99%

“…For instance, trisubstituted boron compounds react with N-donor ligands forming N→B coordinative bonds, here the boron atom changes its coordination number to tetracoordinate producing a tetrahedral geometry. The N→B coordinative bond has resulted in a powerful tool for constructing supramolecular architectures such as macrocycles, capsules, and polymers [24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41]. Previously, we described the synthesis of imine boronic esters by multicomponent reactions and demonstrated their ability to sense metal cations conditioned by the presence of a pyridine fragment in the molecular structure [42][43][44].…”

Section: Introductionmentioning

confidence: 99%

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Six-Membered Heterocyclic Boronate Esters. Synthesis and Structural Analysis

et al. 2022

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Abstract. Nine heterocyclic zwitterionic boronate esters derived from carbonylphenylboronic acids and amino-diols are described. Compounds were prepared by direct condensation reaction between 3- or 4-formyl/acetylphenylboronic acids with 2-amino-2-methyl-1,3-propanediol (1a-1d) or serinol (2-amino-1,3-propanediol) (1e-1h). Compound 2e was obtained by reaction between 4-formylphenylboronic acid and serinol using a solvent mixture methanol/acetone, an aldol condensation reaction was observed. All compounds were characterized by common spectroscopic techniques such as FT-IR, mass spectrometry, and multinuclear 1H, 13C and 11B NMR spectroscopy. 11B NMR spectra showed signals between δ = 1.9 to 7.3 ppm for all compounds, indicating a tetracoordinated environment for the boron atoms in solution. X-ray diffraction analysis showed that boronates are contained in six-membered heterocycles, which have a chair conformation with -OH and -NH3+ substituents in syn disposition. The formation of channels in the crystal lattice that are filled with water and supported by hydrogen bonding interactions is noteworthy. Resumen. En el presente trabajo se describen nueve ésteres de boro zwitteriónicos, derivados de ácidos cabonilfenilborónicos. Los compuestos fueron obtenidos mediante reacciones de condensación entre el ácido 3- o 4- formil/acetilfenilborónico con 2-amino-2-metil propanodiol (1a-1d) o serinol (1e-1h). El compuesto 2e se sintetizó a través del ácido 4-formilfenilborónico y serinol (2-amino-1,3-propanodiol) utilizando una mezcla de disolventes metanol/acetona, dando lugar a una reacción de condensación aldólica. Los compuestos fueron caracterizados por técnicas espectroscópicas como son FT-IR, espectrometría de masas y espectroscopia multinuclear de RMN 1H, 13C y 11B. El espectro RMN de 11B mostró señales anchas entre δ = 1.9 y 7.3 ppm para todos los compuestos, lo cual indica la presencia de átomos de boro tetracoordinados en solución. El análisis por difracción de rayos-X de monocristal mostró la formación de heterociclos de 6 miembros en conformación silla, con una marcada estereoselectividad en donde los grupos -OH y -NH3+ se encuentran en disposición syn. En la red cristalina, se observaron canales ocupados por moléculas de agua y soportados por enlaces de hidrógeno.

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Section: Spectroscopic Analysissupporting

confidence: 58%

Section: General Methods For the Preparation Of Heterocyclic Boronate...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Six-Membered Heterocyclic Boronate Esters. Synthesis and Structural Analysis

et al. 2022

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Boron–Nitrogen Double Tweezers Comprising Arylboronic Esters and Diamines: Self‐Assembly in Solution and Adaptability as Hosts for Aromatic Guests in the Solid State

2020

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The thermodynamic stability of 1 : 1 and 2 : 1 boron–nitrogen (B←N) adducts formed between aromatic boronic esters with mono‐ and diamines was studied in solution by NMR and UV‐vis spectroscopy with association energies (ΔG°) ranging from −11 to −28 kJ mol−1. The effect of different substituents in the boronic ester, the nature of the diamine linker, and the effect of the solvent was explored. Stable 2 : 1 B←N adducts with diamines such as 1,3‐diaminopropane were produced in solutions of hydrogen‐bonding acceptor solvents (acetonitrile and ethyl acetate), which can be isolated in the solid state as crystalline solvates, whereas the use of noncoordinating solvents such as 1,2‐dichloroethane afforded mainly 1 : 1 B←N adducts. In suitable combinations, aromatic bis‐pyridyl diamines produced stable 2 : 1 B←N adducts that were isolated either as solvent‐free solids, solvates, or cocrystals. In these crystalline forms, double‐tweezer hosts were observed with an exceptional syn/anti conformational guest‐adaptability driven by simultaneous donor‐acceptor and C−H⋅⋅⋅π interactions in the tweezer cavities, resembling preorganized covalent tweezer hosts. Interestingly, cocrystals with electron‐rich guests such as tetrathiafulvalene and pyrene showed non‐centrosymmetric crystal lattices with infinite π‐stacked donor–acceptor columns.

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Synthesis and inclusion properties of boroncalix[3]arene compounds obtained by self‐assembly of 3‐aminophenylboronic acid and salicylaldehyde derivatives

Cited by 2 publications

References 65 publications

Six-Membered Heterocyclic Boronate Esters. Synthesis and Structural Analysis

Six-Membered Heterocyclic Boronate Esters. Synthesis and Structural Analysis

Boron–Nitrogen Double Tweezers Comprising Arylboronic Esters and Diamines: Self‐Assembly in Solution and Adaptability as Hosts for Aromatic Guests in the Solid State

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