Influence of methoxy-substituents on the strength of Br ... Br type II halogen bonds in bromobenzoic acid
4-bromo-3,5-di(methoxy)benzoic acid (I) crystallizes in the monoclinic C2/c space group, a = 22.3405 (6) Å, b = 4.85142 (14) Å, c = 18.1583 (5) Å, β = 93.086 (2)°. The crystal structure shows head-to-head dimeric units linked via type II Br ... Br interactions as well as Br ... π and weak H-bonding...
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2016
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Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v1108_n_p235_Raffo http://hdl.handle.net/20.500.12110/paper_00222860_v1108_n_p235_Raffo |
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paper:paper_00222860_v1108_n_p235_Raffo2023-06-08T14:48:50Z Influence of methoxy-substituents on the strength of Br ... Br type II halogen bonds in bromobenzoic acid Alkoxy-substituted benzoic acids Halogen bonds Rationalization of packing modes Type II Br ... Br contact Benzoic acid Catalytic oxidation Crystal structure Electrostatics Iodine Molecular orbitals Electrostatic contributions Electrostatic potentials H-bonding interaction Halogen bonds Intermolecular interactions Rationalization of packing modes Substituted benzoic acids Type II Bromine 4-bromo-3,5-di(methoxy)benzoic acid (I) crystallizes in the monoclinic C2/c space group, a = 22.3405 (6) Å, b = 4.85142 (14) Å, c = 18.1583 (5) Å, β = 93.086 (2)°. The crystal structure shows head-to-head dimeric units linked via type II Br ... Br interactions as well as Br ... π and weak H-bonding interactions. The whole structure exhibits features similar to those of the parent 4-bromobenzoic acid (II), most notably the overall geometrical features involved in the Br ... Br type II interactions. Both structures display comparable C-Br ... Br angles (θ1 = 98.3 and 91.6° and θ2 = 163.0 and 163.5° for (I) and (II) respectively), but the Br ... Br distance is significantly shorter in (I) (3.58 Å) than in (II) (3.81 Å). QM computations provide the magnitude of the intermolecular interactions present in both (I) and (II), and allow disclosing the individual covalent and electrostatic contributions to the Br-Br halogen bond in terms of interaction energies, electrostatic potentials, and a molecular orbital (MO) analysis. © 2015 Elsevier B.V. All rights reserved. 2016 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v1108_n_p235_Raffo http://hdl.handle.net/20.500.12110/paper_00222860_v1108_n_p235_Raffo |
institution |
Universidad de Buenos Aires |
institution_str |
I-28 |
repository_str |
R-134 |
collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
topic |
Alkoxy-substituted benzoic acids Halogen bonds Rationalization of packing modes Type II Br ... Br contact Benzoic acid Catalytic oxidation Crystal structure Electrostatics Iodine Molecular orbitals Electrostatic contributions Electrostatic potentials H-bonding interaction Halogen bonds Intermolecular interactions Rationalization of packing modes Substituted benzoic acids Type II Bromine |
spellingShingle |
Alkoxy-substituted benzoic acids Halogen bonds Rationalization of packing modes Type II Br ... Br contact Benzoic acid Catalytic oxidation Crystal structure Electrostatics Iodine Molecular orbitals Electrostatic contributions Electrostatic potentials H-bonding interaction Halogen bonds Intermolecular interactions Rationalization of packing modes Substituted benzoic acids Type II Bromine Influence of methoxy-substituents on the strength of Br ... Br type II halogen bonds in bromobenzoic acid |
topic_facet |
Alkoxy-substituted benzoic acids Halogen bonds Rationalization of packing modes Type II Br ... Br contact Benzoic acid Catalytic oxidation Crystal structure Electrostatics Iodine Molecular orbitals Electrostatic contributions Electrostatic potentials H-bonding interaction Halogen bonds Intermolecular interactions Rationalization of packing modes Substituted benzoic acids Type II Bromine |
description |
4-bromo-3,5-di(methoxy)benzoic acid (I) crystallizes in the monoclinic C2/c space group, a = 22.3405 (6) Å, b = 4.85142 (14) Å, c = 18.1583 (5) Å, β = 93.086 (2)°. The crystal structure shows head-to-head dimeric units linked via type II Br ... Br interactions as well as Br ... π and weak H-bonding interactions. The whole structure exhibits features similar to those of the parent 4-bromobenzoic acid (II), most notably the overall geometrical features involved in the Br ... Br type II interactions. Both structures display comparable C-Br ... Br angles (θ1 = 98.3 and 91.6° and θ2 = 163.0 and 163.5° for (I) and (II) respectively), but the Br ... Br distance is significantly shorter in (I) (3.58 Å) than in (II) (3.81 Å). QM computations provide the magnitude of the intermolecular interactions present in both (I) and (II), and allow disclosing the individual covalent and electrostatic contributions to the Br-Br halogen bond in terms of interaction energies, electrostatic potentials, and a molecular orbital (MO) analysis. © 2015 Elsevier B.V. All rights reserved. |
title |
Influence of methoxy-substituents on the strength of Br ... Br type II halogen bonds in bromobenzoic acid |
title_short |
Influence of methoxy-substituents on the strength of Br ... Br type II halogen bonds in bromobenzoic acid |
title_full |
Influence of methoxy-substituents on the strength of Br ... Br type II halogen bonds in bromobenzoic acid |
title_fullStr |
Influence of methoxy-substituents on the strength of Br ... Br type II halogen bonds in bromobenzoic acid |
title_full_unstemmed |
Influence of methoxy-substituents on the strength of Br ... Br type II halogen bonds in bromobenzoic acid |
title_sort |
influence of methoxy-substituents on the strength of br ... br type ii halogen bonds in bromobenzoic acid |
publishDate |
2016 |
url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v1108_n_p235_Raffo http://hdl.handle.net/20.500.12110/paper_00222860_v1108_n_p235_Raffo |
_version_ |
1768542114408300544 |