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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Autores principales: Raffo, P.A., Marcolongo, J.P., Funes, A.V., Slep, L.D., Baggio, R.F., Cukiernik, F.D.
Formato: JOUR
Materias:
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
Intermolecular interactions
Substituted benzoic acids
Type II
Bromine
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00222860_v1108_n_p235_Raffo
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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_00222860_v1108_n_p235_Raffo2023-10-03T14:30:31Z Influence of methoxy-substituents on the strength of Br ... Br type II halogen bonds in bromobenzoic acid Raffo, P.A. Marcolongo, J.P. Funes, A.V. Slep, L.D. Baggio, R.F. Cukiernik, F.D. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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
Raffo, P.A.
Marcolongo, J.P.
Funes, A.V.
Slep, L.D.
Baggio, R.F.
Cukiernik, F.D.
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.
format JOUR
author Raffo, P.A.
Marcolongo, J.P.
Funes, A.V.
Slep, L.D.
Baggio, R.F.
Cukiernik, F.D.
author_facet Raffo, P.A.
Marcolongo, J.P.
Funes, A.V.
Slep, L.D.
Baggio, R.F.
Cukiernik, F.D.
author_sort Raffo, P.A.
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
url http://hdl.handle.net/20.500.12110/paper_00222860_v1108_n_p235_Raffo
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