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Halogen Bonds in 2,5-Dihalopyridine-Copper(I) Halide Coordination Polymers
Two series of 2,5-dihalopyridine-Cu(I)A (A = I, Br) complexes based on 2-X-5-iodopyridine and 2-X-5-bromopyridine (X = F, Cl, Br and I) are characterized by using single-crystal X-ray diffraction analysis to examine the nature of C2−X2···A–Cu and C5−X5···A–Cu halogen bonds. The reaction of the 2,5-d...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6829255/ https://www.ncbi.nlm.nih.gov/pubmed/31614477 http://dx.doi.org/10.3390/ma12203305 |
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author | von Essen, Carolina Rissanen, Kari Puttreddy, Rakesh |
author_facet | von Essen, Carolina Rissanen, Kari Puttreddy, Rakesh |
author_sort | von Essen, Carolina |
collection | PubMed |
description | Two series of 2,5-dihalopyridine-Cu(I)A (A = I, Br) complexes based on 2-X-5-iodopyridine and 2-X-5-bromopyridine (X = F, Cl, Br and I) are characterized by using single-crystal X-ray diffraction analysis to examine the nature of C2−X2···A–Cu and C5−X5···A–Cu halogen bonds. The reaction of the 2,5-dihalopyridines and Cu(I) salts allows the synthesis of eight 1-D coordination polymers and a discrete structure. The resulting Cu(I)-complexes are linked by C−X···A–Cu halogen bonds forming 3-D supramolecular networks. The C−X···A–Cu halogen bonds formed between halopyridine ligands and copper(I)-bound halide ions are stronger than C−X···X’–C interactions between two 2,5-dihalopyridine ligands. The C5−I5···I–Cu and C5−Br5···Br–Cu halogens bonds are shorter for C2-fluorine than C2-chlorine due to the greater electron-withdrawing power of fluorine. In 2,5-diiodopyridine-Cu(I)Br complex, the shorter C2−I2···Br–Cu [3.473(5) Å] distances are due to the combined polarization of C2-iodine by C2−I2···Cu interactions and para-electronic effects offered by the C5-iodine, whilst the long halogen bond contacts for C5−I5···Br–Cu [3.537(5) Å] are indicative that C2-iodine has a less para-electronic influence on the C5-iodine. In 2-fluoro-5-X-pyridine-Cu(I) complexes, the C2-fluorine is halogen bond passive, while the other C2-halogens in 2,5-dihalopyridine-Cu(I), including C2-chlorine, participate in halogen bonding interactions. |
format | Online Article Text |
id | pubmed-6829255 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-68292552019-11-18 Halogen Bonds in 2,5-Dihalopyridine-Copper(I) Halide Coordination Polymers von Essen, Carolina Rissanen, Kari Puttreddy, Rakesh Materials (Basel) Article Two series of 2,5-dihalopyridine-Cu(I)A (A = I, Br) complexes based on 2-X-5-iodopyridine and 2-X-5-bromopyridine (X = F, Cl, Br and I) are characterized by using single-crystal X-ray diffraction analysis to examine the nature of C2−X2···A–Cu and C5−X5···A–Cu halogen bonds. The reaction of the 2,5-dihalopyridines and Cu(I) salts allows the synthesis of eight 1-D coordination polymers and a discrete structure. The resulting Cu(I)-complexes are linked by C−X···A–Cu halogen bonds forming 3-D supramolecular networks. The C−X···A–Cu halogen bonds formed between halopyridine ligands and copper(I)-bound halide ions are stronger than C−X···X’–C interactions between two 2,5-dihalopyridine ligands. The C5−I5···I–Cu and C5−Br5···Br–Cu halogens bonds are shorter for C2-fluorine than C2-chlorine due to the greater electron-withdrawing power of fluorine. In 2,5-diiodopyridine-Cu(I)Br complex, the shorter C2−I2···Br–Cu [3.473(5) Å] distances are due to the combined polarization of C2-iodine by C2−I2···Cu interactions and para-electronic effects offered by the C5-iodine, whilst the long halogen bond contacts for C5−I5···Br–Cu [3.537(5) Å] are indicative that C2-iodine has a less para-electronic influence on the C5-iodine. In 2-fluoro-5-X-pyridine-Cu(I) complexes, the C2-fluorine is halogen bond passive, while the other C2-halogens in 2,5-dihalopyridine-Cu(I), including C2-chlorine, participate in halogen bonding interactions. MDPI 2019-10-11 /pmc/articles/PMC6829255/ /pubmed/31614477 http://dx.doi.org/10.3390/ma12203305 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article von Essen, Carolina Rissanen, Kari Puttreddy, Rakesh Halogen Bonds in 2,5-Dihalopyridine-Copper(I) Halide Coordination Polymers |
title | Halogen Bonds in 2,5-Dihalopyridine-Copper(I) Halide Coordination Polymers |
title_full | Halogen Bonds in 2,5-Dihalopyridine-Copper(I) Halide Coordination Polymers |
title_fullStr | Halogen Bonds in 2,5-Dihalopyridine-Copper(I) Halide Coordination Polymers |
title_full_unstemmed | Halogen Bonds in 2,5-Dihalopyridine-Copper(I) Halide Coordination Polymers |
title_short | Halogen Bonds in 2,5-Dihalopyridine-Copper(I) Halide Coordination Polymers |
title_sort | halogen bonds in 2,5-dihalopyridine-copper(i) halide coordination polymers |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6829255/ https://www.ncbi.nlm.nih.gov/pubmed/31614477 http://dx.doi.org/10.3390/ma12203305 |
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