Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols

Ten 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 de...

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Autores principales: Tsang, M.Y., Di Salvo, F., Teixidor, F., Viñas, C., Planas, J.G., Choquesillo-Lazarte, D., Vanthuyne, N.
Formato: JOUR
Materias:
Chirality
Crystallography
Hydrogen bonds
Single crystals
Stereochemistry
Supramolecular chemistry
Cambridge Structural Databases
Carborane derivatives
Hydrogen bond donors
Molecular chirality
Single crystal X-ray crystallography
Supramolecular chirality
Torsion angle
X-ray structure
X ray crystallography
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_15287483_v15_n2_p935_Tsang
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling todo:paper_15287483_v15_n2_p935_Tsang2023-10-03T16:21:10Z Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols Tsang, M.Y. Di Salvo, F. Teixidor, F. Viñas, C. Planas, J.G. Choquesillo-Lazarte, D. Vanthuyne, N. Chirality Crystallography Hydrogen bonds Single crystals Stereochemistry Supramolecular chemistry Cambridge Structural Databases Carborane derivatives Hydrogen bond donors Molecular chirality Single crystal X-ray crystallography Supramolecular chirality Torsion angle X-ray structure X ray crystallography Ten 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⋯N hydrogen bonded homochiral 21-helical networks, except that for rac-3a, which forms O-H⋯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⋯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. © 2015 American Chemical Society. Fil:Di Salvo, F. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_15287483_v15_n2_p935_Tsang
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Chirality
Crystallography
Hydrogen bonds
Single crystals
Stereochemistry
Supramolecular chemistry
Cambridge Structural Databases
Carborane derivatives
Hydrogen bond donors
Molecular chirality
Single crystal X-ray crystallography
Supramolecular chirality
Torsion angle
X-ray structure
X ray crystallography
spellingShingle Chirality
Crystallography
Hydrogen bonds
Single crystals
Stereochemistry
Supramolecular chemistry
Cambridge Structural Databases
Carborane derivatives
Hydrogen bond donors
Molecular chirality
Single crystal X-ray crystallography
Supramolecular chirality
Torsion angle
X-ray structure
X ray crystallography
Tsang, M.Y.
Di Salvo, F.
Teixidor, F.
Viñas, C.
Planas, J.G.
Choquesillo-Lazarte, D.
Vanthuyne, N.
Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols
topic_facet Chirality
Crystallography
Hydrogen bonds
Single crystals
Stereochemistry
Supramolecular chemistry
Cambridge Structural Databases
Carborane derivatives
Hydrogen bond donors
Molecular chirality
Single crystal X-ray crystallography
Supramolecular chirality
Torsion angle
X-ray structure
X ray crystallography
description Ten 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⋯N hydrogen bonded homochiral 21-helical networks, except that for rac-3a, which forms O-H⋯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⋯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. © 2015 American Chemical Society.
format JOUR
author Tsang, M.Y.
Di Salvo, F.
Teixidor, F.
Viñas, C.
Planas, J.G.
Choquesillo-Lazarte, D.
Vanthuyne, N.
author_facet Tsang, M.Y.
Di Salvo, F.
Teixidor, F.
Viñas, C.
Planas, J.G.
Choquesillo-Lazarte, D.
Vanthuyne, N.
author_sort Tsang, M.Y.
title Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols
title_short Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols
title_full Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols
title_fullStr Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols
title_full_unstemmed Is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols
title_sort is molecular chirality connected to supramolecular chirality? the particular case of chiral 2-pyridyl alcohols
url http://hdl.handle.net/20.500.12110/paper_15287483_v15_n2_p935_Tsang
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