Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: syntheses, crystal structures and melting points correlation

Salvo, Florencia Di; García, Yolanda; Teixidor, Francesç; Viñas, Clara; Planas, José Giner; Light, Mark E.; Hursthouse, Michael B.

doi:10.1039/c1ce05449j

Cited by 32 publications

(28 citation statements)

References 58 publications

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“…The supramolecular structure for racemic rac-1a 19 agrees with that of the enantiopure R-1a and S-1a structures, in the sense that, both supramolecular homochiral P-and M-helices are observed in the solid state (Table 1 and Figure S8 in SI). Helices of opposite handedness pack in the solid state in rac-1a.…”

Section: ■ Results and Discussionsupporting

confidence: 73%

Is Molecular Chirality Connected to Supramolecular Chirality? The Particular Case of Chiral 2-Pyridyl Alcohols

Tsang

Salvo

Teixidor

et al. 2015

Crystal Growth & Design

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International audienceTen structurally related racemic 2-pyridylmethyl alcohols containing an o-carborane core (1,2-closo-C2B10H10; rac-1a) or m-carborane (1,7-closo-C2B10H10; rac-2a) or p-carborane (1,7-closo-C2B10H10; rac-3a) and their enantiopure forms (R- and S-1a or R- and S-2a or R- and S-3a), as well as an iodo derivative of rac-3a (rac-4a) and a non-carborane derivative (C6H5; rac-5) have been studied by single crystal X-ray crystallography. All racemic and enantiopure structures show O-H center dot center dot center dot N hydrogen bonded homochiral 21-helical networks, except that for rac-3a, which forms O-H center dot center dot center dot N hydrogen bonded trimers. A comparison of these X-ray structures with that for others found in the Cambridge Structural Database for chiral 2-pyridyl alcohols-either in racemic or enantiopure forms-that form O-H center dot center dot center dot N hydrogen bonded homochiral 21-helical networks reveals a possible relationship between the torsion angle of the hydrogen bond donor and acceptor groups in these molecules and the hydrogen bonded supramolecular helices formed in the solid state

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Section: ■ Results and Discussionsupporting

confidence: 73%

Is Molecular Chirality Connected to Supramolecular Chirality? The Particular Case of Chiral 2-Pyridyl Alcohols

Tsang

Salvo

Teixidor

et al. 2015

Crystal Growth & Design

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“…For example, 45% of the molecular surface contributes to the dispersion C-HÁ Á ÁH-C interactions, and less than 15% to the C-HÁ Á ÁCl bonds, whilst their contributions to the packing energy are similar. This fact is in good agreement with the significant impact of hydrogen bonds and the small impact of HÁ Á ÁH interactions on the lattice energy (Dean et al, 2008;Di Salvo et al, 2011;Grabowsky et al, 2012;Korlyukov et al, 2015) of molecular compounds. Besides, Grabowsky et al (2012) mentioned that the contribution of C-HÁ Á Á and Á Á Á contacts to the lattice energies should be estimated as the sum of CÁ Á ÁH and CÁ Á ÁC Selected QTAIM parameters of weak intermolecular interactions in the crystal of (I).…”

Section: Intermolecular Bondingsupporting

confidence: 86%

Combined analysis of chemical bonding in a Cu^IIdimer using QTAIM, Voronoi tessellation and Hirshfeld surface approaches

Вологжанина

Kats

Penkova

et al. 2015

Acta Crystallogr Sect B

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Interaction of 1-(1H-pyrazol-5-yl)ethanone oxime (H2PzOx) with copper(II) chloride in the presence of pyridine afforded a binuclear discrete [Cu2(HPzOx)2Cl2py2] complex, which was characterized by Fourier transform-IR and electron paramagnetic resonance (EPR) spectra, magnetochemistry and high-resolution X-ray diffraction experiments. Multipole refinement of X-ray diffraction data and density-functional theory (DFT) calculations of an isolated molecule allowed charge and spin distributions to be obtained for this compound. Magnetochemistry data, EPR spectra and DFT calculations of an isolated molecule show antiferromagnetic coupling between copper(II) ions. The spin distribution suggests an exchange pathway via the bridging pyrazole ring in the equatorial plane of the CuN4Cl coordination polyhedron, thus providing support for the classical superexchange mechanism; the calculated value of the magnetic coupling constant -2J is equal to 220 cm(-1), which compares well with the experimental value of 203 ± 2 cm(-1). Chemical connectivity was derived by Bader's 'quantum theory of atoms in molecules' and compared with Voronoi tessellation and Hirshfeld surface representations of crystal space. All methodologies gave a similar qualitative and semi-quantitative description of intra- and intermolecular connectivity.

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“…In the Hirshfeld surface approach, the role of hydrogen bonds and specific interaction is underestimated and that of π···π and C-H···H-C bonds is overestimated. Indeed, small impact of H···H interactions on the lattice energy of molecular compounds was recently demonstrated [72][73][74] based on molecular Hirshfeld surface approach.…”

Section: Peculiarities Of Supramolecular Organizationmentioning

confidence: 99%

Understanding the structure of salicyl hydrazone metallocomplexes: crystal structure, AIM and Hirshfeld surface analysis of trichloro-(N-salicylidenebenzoylhydrazinato-N,O,O′)-tin(IV)

et al. 2015

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The results of detailed experimental and theoretical study of chemical intra-and intermolecular bonding of salicyl hydrazone complex with SnCl 3 are described. The chemical bonding pattern in the crystal and isolated molecule is described in terms of Bader's "Atoms in Molecules" (AIM) theory. Analysis of AIM charges has revealed that amount of charge transferred from ligand to SnCl 3 moiety is equal to ≈ 0.3 e that leads to significant redistribution of bond lengths as compared to other tin(IV) salicyl hydrazonates. Comparison of geometry and characteristics of electron density distribution indicates the weakening of coordination Sn-O and Sn-N bonds in isolated molecule in comparison with crystal up to 10 kcal/mol. This effect was explained by the intermolecular H···Cl bonding. According to the Hirshfeld surface analysis, these interactions have the most pronounced contribution to the crystal packing energy. The significance of the present article lies in both the detailed inspection of the crystal packing effect on the coordination bonds of the tin(IV) atom and intermolecular interactions governing the supramolecular self-assembly of hydrogen-bonded chains by means of specific interactions and π···π stacking.

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Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: syntheses, crystal structures and melting points correlation

Cited by 32 publications

References 58 publications

Is Molecular Chirality Connected to Supramolecular Chirality? The Particular Case of Chiral 2-Pyridyl Alcohols

Is Molecular Chirality Connected to Supramolecular Chirality? The Particular Case of Chiral 2-Pyridyl Alcohols

Combined analysis of chemical bonding in a Cu^IIdimer using QTAIM, Voronoi tessellation and Hirshfeld surface approaches

Understanding the structure of salicyl hydrazone metallocomplexes: crystal structure, AIM and Hirshfeld surface analysis of trichloro-(N-salicylidenebenzoylhydrazinato-N,O,O′)-tin(IV)

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Supramolecular architectures in o-carboranyl alcohols bearing N-aromatic rings: syntheses, crystal structures and melting points correlation

Cited by 32 publications

References 58 publications

Is Molecular Chirality Connected to Supramolecular Chirality? The Particular Case of Chiral 2-Pyridyl Alcohols

Is Molecular Chirality Connected to Supramolecular Chirality? The Particular Case of Chiral 2-Pyridyl Alcohols

Combined analysis of chemical bonding in a CuIIdimer using QTAIM, Voronoi tessellation and Hirshfeld surface approaches

Understanding the structure of salicyl hydrazone metallocomplexes: crystal structure, AIM and Hirshfeld surface analysis of trichloro-(N-salicylidenebenzoylhydrazinato-N,O,O′)-tin(IV)

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Combined analysis of chemical bonding in a Cu^IIdimer using QTAIM, Voronoi tessellation and Hirshfeld surface approaches