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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" (2016) Journal of Molecular Structure. 1108:235-244
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Abstract:

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.

Registro:

Documento: Artículo
Título:Influence of methoxy-substituents on the strength of Br ... Br type II halogen bonds in bromobenzoic acid
Autor:Raffo, P.A.; Marcolongo, J.P.; Funes, A.V.; Slep, L.D.; Baggio, R.F.; Cukiernik, F.D.
Filiación:DQIAQF-INQUIMAE, Facultad de Ciencias Exactas, Naturales Universidad de Buenos Aires Pabello II Cdad, Universitaria - Nuñez, Caba, C1428EGA, Argentina
Gerencia de Investigación y Aplicaciones, Centro Atómico Constituyentes, Comisión Nacional de Energía Atómica, Buenos Aires, Argentina
Palabras clave: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
Año:2016
Volumen:1108
Página de inicio:235
Página de fin:244
DOI: http://dx.doi.org/10.1016/j.molstruc.2015.12.016
Título revista:Journal of Molecular Structure
Título revista abreviado:J. Mol. Struct.
ISSN:00222860
CODEN:JMOSB
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v1108_n_p235_Raffo

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Citas:

---------- APA ----------
Raffo, P.A., Marcolongo, J.P., Funes, A.V., Slep, L.D., Baggio, R.F. & Cukiernik, F.D. (2016) . Influence of methoxy-substituents on the strength of Br ... Br type II halogen bonds in bromobenzoic acid. Journal of Molecular Structure, 1108, 235-244.
http://dx.doi.org/10.1016/j.molstruc.2015.12.016
---------- CHICAGO ----------
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" . Journal of Molecular Structure 1108 (2016) : 235-244.
http://dx.doi.org/10.1016/j.molstruc.2015.12.016
---------- MLA ----------
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" . Journal of Molecular Structure, vol. 1108, 2016, pp. 235-244.
http://dx.doi.org/10.1016/j.molstruc.2015.12.016
---------- VANCOUVER ----------
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. J. Mol. Struct. 2016;1108:235-244.
http://dx.doi.org/10.1016/j.molstruc.2015.12.016