Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine

4′-Substituted derivatives of 2,2′:6′,2′′-terpyridine with N-containing heteroaromatic substituents, such as pyridyl groups, might be able to coordinate metal centres through the extra N-donor atom, in addition to the chelating terpyridine N atoms. The incorporation of these peripheral N-donor sites...

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Autores principales: Granifo, J., Arévalo, B., Gaviño, R., Suárez, S., Baggio, R.
Formato: JOUR
Materias:
4′-substituted 2,2′:6′,2′′-terpyridine
AIM
atoms-in-molecules
attractive H⋯H interaction
Bader's theory
crystal structure
theoretical characterization
Atoms
Crystal structure
Hydrogen bonds
Ions
Molecules
Atoms in Molecules
Bonding character
Columnar arrays
Non-covalent interaction
Supramolecular structure
Terpyridines
Title compounds
attractive H..H interaction
Crystal atomic structure
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_20532296_v72_n_p932_Granifo
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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_20532296_v72_n_p932_Granifo2023-10-03T16:39:00Z Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine Granifo, J. Arévalo, B. Gaviño, R. Suárez, S. Baggio, R. 4′-substituted 2,2′:6′,2′′-terpyridine AIM atoms-in-molecules attractive H⋯H interaction Bader's theory crystal structure theoretical characterization Atoms Crystal structure Hydrogen bonds Ions Molecules Atoms in Molecules Bader's theory Bonding character Columnar arrays Non-covalent interaction Supramolecular structure Terpyridines Title compounds attractive H..H interaction Crystal atomic structure 4′-Substituted derivatives of 2,2′:6′,2′′-terpyridine with N-containing heteroaromatic substituents, such as pyridyl groups, might be able to coordinate metal centres through the extra N-donor atom, in addition to the chelating terpyridine N atoms. The incorporation of these peripheral N-donor sites would also allow for the diversification of the types of noncovalent interactions present, such as hydrogen bonding and π-π stacking. The title compound, C24H16N4, consists of a 2,2′:6′,2′′-terpyridine nucleus (tpy), with a pendant isoquinoline group (isq) bound at the central pyridine (py) ring. The tpy nucleus deviates slightly from planarity, with interplanar angles between the lateral and central py rings in the range 2.24(7)-7.90(7)°, while the isq group is rotated significantly [by 46.57(6)°] out of this planar scheme, associated with a short Htpy⋯Hisq contact of 2.32Å. There are no strong noncovalent interactions in the structure, the main ones being of the π-π and C - H⋯π types, giving rise to columnar arrays along [001], further linked by C - H⋯N hydrogen bonds into a three-dimensional supramolecular structure. An Atoms In Molecules (AIM) analysis of the noncovalent interactions provided illuminating results, and while confirming the bonding character for all those interactions unquestionable from a geometrical point of view, it also provided answers for some cases where geometric parameters are not informative, in particular, the short Htpy⋯Hisq contact of 2.32Å to which AIM ascribed an attractive character. © 2016 International Union of Crystallography. Fil:Suárez, S. 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_20532296_v72_n_p932_Granifo
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic 4′-substituted 2,2′:6′,2′′-terpyridine
AIM
atoms-in-molecules
attractive H⋯H interaction
Bader's theory
crystal structure
theoretical characterization
Atoms
Crystal structure
Hydrogen bonds
Ions
Molecules
Atoms in Molecules
Bader's theory
Bonding character
Columnar arrays
Non-covalent interaction
Supramolecular structure
Terpyridines
Title compounds
attractive H..H interaction
Crystal atomic structure
spellingShingle 4′-substituted 2,2′:6′,2′′-terpyridine
AIM
atoms-in-molecules
attractive H⋯H interaction
Bader's theory
crystal structure
theoretical characterization
Atoms
Crystal structure
Hydrogen bonds
Ions
Molecules
Atoms in Molecules
Bader's theory
Bonding character
Columnar arrays
Non-covalent interaction
Supramolecular structure
Terpyridines
Title compounds
attractive H..H interaction
Crystal atomic structure
Granifo, J.
Arévalo, B.
Gaviño, R.
Suárez, S.
Baggio, R.
Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
topic_facet 4′-substituted 2,2′:6′,2′′-terpyridine
AIM
atoms-in-molecules
attractive H⋯H interaction
Bader's theory
crystal structure
theoretical characterization
Atoms
Crystal structure
Hydrogen bonds
Ions
Molecules
Atoms in Molecules
Bader's theory
Bonding character
Columnar arrays
Non-covalent interaction
Supramolecular structure
Terpyridines
Title compounds
attractive H..H interaction
Crystal atomic structure
description 4′-Substituted derivatives of 2,2′:6′,2′′-terpyridine with N-containing heteroaromatic substituents, such as pyridyl groups, might be able to coordinate metal centres through the extra N-donor atom, in addition to the chelating terpyridine N atoms. The incorporation of these peripheral N-donor sites would also allow for the diversification of the types of noncovalent interactions present, such as hydrogen bonding and π-π stacking. The title compound, C24H16N4, consists of a 2,2′:6′,2′′-terpyridine nucleus (tpy), with a pendant isoquinoline group (isq) bound at the central pyridine (py) ring. The tpy nucleus deviates slightly from planarity, with interplanar angles between the lateral and central py rings in the range 2.24(7)-7.90(7)°, while the isq group is rotated significantly [by 46.57(6)°] out of this planar scheme, associated with a short Htpy⋯Hisq contact of 2.32Å. There are no strong noncovalent interactions in the structure, the main ones being of the π-π and C - H⋯π types, giving rise to columnar arrays along [001], further linked by C - H⋯N hydrogen bonds into a three-dimensional supramolecular structure. An Atoms In Molecules (AIM) analysis of the noncovalent interactions provided illuminating results, and while confirming the bonding character for all those interactions unquestionable from a geometrical point of view, it also provided answers for some cases where geometric parameters are not informative, in particular, the short Htpy⋯Hisq contact of 2.32Å to which AIM ascribed an attractive character. © 2016 International Union of Crystallography.
format JOUR
author Granifo, J.
Arévalo, B.
Gaviño, R.
Suárez, S.
Baggio, R.
author_facet Granifo, J.
Arévalo, B.
Gaviño, R.
Suárez, S.
Baggio, R.
author_sort Granifo, J.
title Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
title_short Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
title_full Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
title_fullStr Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
title_full_unstemmed Structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
title_sort structural and theoretical characterization of a new twisted 4′-substituted terpyridine compound: 4′-(isoquinolin-4-yl)-2,2′:6′,2′′-terpyridine
url http://hdl.handle.net/20.500.12110/paper_20532296_v72_n_p932_Granifo
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AT arevalob structuralandtheoreticalcharacterizationofanewtwisted4substitutedterpyridinecompound4isoquinolin4yl2262terpyridine
AT gavinor structuralandtheoreticalcharacterizationofanewtwisted4substitutedterpyridinecompound4isoquinolin4yl2262terpyridine
AT suarezs structuralandtheoreticalcharacterizationofanewtwisted4substitutedterpyridinecompound4isoquinolin4yl2262terpyridine
AT baggior structuralandtheoreticalcharacterizationofanewtwisted4substitutedterpyridinecompound4isoquinolin4yl2262terpyridine
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