General Access to Aminobenzyl‐<i>o</i>‐carboranes as a New Class of Carborane Derivatives: Entry to Enantiopure Carborane–Amine Combinations

Terrasson, Vincent; Planas, José Giner; Prim, Damien; Teixidor, Francesç; Viñas, Clara; Light, Mark E.; Hursthouse, Michael B.

doi:10.1002/chem.200901332

Cited by 22 publications

(4 citation statements)

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“…Using this methodology, a wide variety of mono substituted carboranyl methanol derivatives have been synthesized [42,43]. Following a similar procedure we [44][45][46][47][48][49] and others [50,51] have prepared an extensive series of new monosubstituted o-, m-and p-carboranylmethylalcohols bearing nitrogenated aromatic rings, by the addition of lithiocarboranes to the corresponding pyridylaldehydes (1-4, Chart 1 and Scheme 1). The addition of dilithiocarboranes to two equivalents of the corresponding aldehydes, under the same reaction conditions, provided a new series of disubstituted o-and m-carboranylmethylalcohols (5-6, Chart 1) [52,53].…”

Section: Closo-carboranylmethylalcohols With Nitrogenated Aromatic Ringsmentioning

confidence: 99%

N,O-Type Carborane-Based Materials

2016

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This review summarizes the synthesis and coordination chemistry of a series of carboranyl ligands containing N,O donors. Such carborane-based ligands are scarcely reported in the literature when compared to other heteroatom-containing donors. The synthetic routes for metal complexes of these N,O-type carborane ligands are summarized and the properties of such complexes are described in detail. Particular attention is paid to the effect that the incorporation of carboranes has into the coordination chemistry of the otherwise carbon-based ligands and the properties of such materials. The reported complexes show a variety of properties such as those used in magnetic, chiroptical, nonlinear optical, catalytic and biomedical applications.

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Section: Closo-carboranylmethylalcohols With Nitrogenated Aromatic Ringsmentioning

confidence: 99%

N,O-Type Carborane-Based Materials

2016

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“…Such carborane derivatives thus remain challenging and under-exploited from synthetic, coordination chemistry, and, consequently, applications points of view . On the basis of our previous experience in both carborane chemistry and synthesis, complexation, and catalytic activity of benzylic amines, we have been interested in the synthesis of new carboranyl amines. Our efforts to date have focused on aminobenzyl- o -carboranes bearing (hetero)aromatic rings (type III in Scheme ).…”

Section: Introductionmentioning

confidence: 99%

closo-o-Carboranylmethylamine−Pyridine Associations: Synthesis, Characterization, and First Complexation Studies

et al. 2010

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The synthesis of new pyridine-substituted carboranylmethylamines is described. The strategy involved mesylation of carboranylmethanols prior to amination reaction and is particularly adapted to the reactivity of o-carborane derivatives bearing a 2-pyridinyl substituent. Preparation and characterization of a corresponding N,N-ligand-palladium complex as well as first results in a Suzuki coupling reaction are illustrated.

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“…Nowadays, information about the crystal structures of discrete organic and organometallic compounds allows us to reformulate principles of their packing [23,24], and to investigate intermolecular interactions more thoroughly. Not only information about geometry and frequency of occurrence of an unusual interaction, synthon, or tecton is extracted from the CSD to support a conclusion about its' role in crystal packing and electronic effects that cause its' appearance [25][26][27][28][29]; but it is also recommended to additionally compare interaction occurrence relative to what would be expected at random [30][31][32][33]. Crystals 2019, 9, 478 3 of 40Data about molecular geometry-from bond lengths and angles to torsions and ring geometry-form the basis of our understanding of the energetics of molecular conformation.…”

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Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

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2019

Crystals

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Intermolecular interactions of organic, inorganic, and organometallic compounds are the key to many composition-structure and structure-property networks. In this review, some of these relations and the tools developed by the Cambridge Crystallographic Data Center (CCDC) to analyze them and design solid forms with desired properties are described. The potential of studies supported by the Cambridge Structural Database (CSD)-Materials tools for investigation of dynamic processes in crystals, for analysis of biologically active, high energy, optical, (electro)conductive, and other functional crystalline materials, and for the prediction of novel solid forms (polymorphs, co-crystals, solvates) are discussed. Besides, some unusual applications, the potential for further development and limitations of the CCDC software are reported. Crystals 2019, 9, 478 2 of 40 these fields, the manuscript cites only (i) recent works devoted to the analysis of correlations between intermolecular interactions and properties of a small molecule (for example its inclination to form polymorphs, solvates, and co-crystals), or a corresponding solid (from a well-known requirement for non-linear optical materials to crystallize in acentric space groups, to recent studies devoted to the effect of solvent presence on mechanical properties), and (ii) the corresponding software developed to investigate these correlations and to design novel solid forms with desired physicochemical properties. As the description of structure-property networks describes mainly the papers published in the last 10 years in the field of organic, organometallic, and coordination crystals, then the software under discussion will be limited with those developed by the Cambridge Crystallographic Data Centre (CCDC) for material chemistry and crystallography. Various examples of applications of the CCDC software to functional materials including their combination with other software, and restrictions found, will be given.First, the Cambridge Structural Database (CSD) and components of the CSD-Enterprise will be described in Section 2. Then, some properties related to the appearance of a given supramolecular associate, and the tools to search for an associate in the CSD will be reported in Section 3. The properties of solids dependent on the crystal morphology, the Bravais, Friedel, Donnay, and Harker (BFDH) tool for crystal morphology prediction and its' application to affect crystal morphology, polymorphism, and solvatomorphism will be reported in Section 4. Knowledge-based predictions of H-bonded polymorphism, co-crystal formation, mapping of likely intermolecular interactions, and conformer generation for the synthesis of novel functional materials will be discussed in Section 5, and the analysis of local connectivity and whole architectures of solvent molecules in Section 6. Finally, Section 7 contains information about Python API algorithms compatible with the CSD-Enterprise and about some examples of the successful combination of the CSD-Enterprise tools with exte...

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General Access to Aminobenzyl‐o‐carboranes as a New Class of Carborane Derivatives: Entry to Enantiopure Carborane–Amine Combinations

Cited by 22 publications

References 88 publications

N,O-Type Carborane-Based Materials

N,O-Type Carborane-Based Materials

closo-o-Carboranylmethylamine−Pyridine Associations: Synthesis, Characterization, and First Complexation Studies

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

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