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Abstract:

The crystalline structure of four alkoxy-substituted benzoic acids, namely 3-(methoxy)benzoic acid (I), (with two independent molecules in the asymmetric unit); 3,4-di(ethoxy)benzoic acid (II), 3,5-di(ethoxy)benzoic acid (III) and 3,4,5-tri(ethoxy)benzoic acid (IV) are presented, and the details of their packing arrangements discussed. In all cases the synthon is a H-bonded head-to-head dimer. C-Hπ interactions involving C atoms at the 4-positions of neighbouring molecules organize the dimeric synthons in a perpendicular orientation in the case of I. These interactions being blocked for II, Van der Waals interchain interactions organise synthons therein in parallel orientation. In the case of III, although C-Hπ interactions at the 4-positions are possible in principle, interchain interactions prevail, giving rise to a parallel arrangement of linear strands. Finally, compound IV with all three 3,4,5 substituted sites reduces its interaction scheme to stacking contacts, and the columns thus formed are essentially non interacting. An attempt to rationalize the molecular factors influencing the structures of the whole set of 3-, 4- and/or 5-methoxy- and ethoxy-substituted benzoic acids reported so far in the literature is performed. © 2014 Elsevier B.V. All rights reserved.

Registro:

Documento: Artículo
Título:Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures
Autor:Raffo, P.A.; Rossi, L.; Alborés, P.; Baggio, R.F.; Cukiernik, F.D.
Filiación:INQUIMAE, Departamento de Química Inorgánica, Analítica y Química Física, Universidad de Buenos Aires, Pabellón II, (C1428EHA), CABA, Argentina
Gerencia de Investigación y Aplicaciones, Centro Atómico Constituyentes, Comisión Nacional de Energía Atómica, Buenos Aires, Argentina
Palabras clave:Alkoxy-substituted benzoic acids; Rationalization of packing modes; ππ and C-Hπ interactions; Catalytic oxidation; Dimers; Molecules; Van der Waals forces; Crystalline structure; Head-to-head dimers; Interaction schemes; Interchain interactions; Parallel arrangement; Parallel orientation; Perpendicular orientation; Rationalization of packing modes; Benzoic acid
Año:2014
Volumen:1070
Número:1
Página de inicio:86
Página de fin:93
DOI: http://dx.doi.org/10.1016/j.molstruc.2014.04.003
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_v1070_n1_p86_Raffo

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Citas:

---------- APA ----------
Raffo, P.A., Rossi, L., Alborés, P., Baggio, R.F. & Cukiernik, F.D. (2014) . Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures. Journal of Molecular Structure, 1070(1), 86-93.
http://dx.doi.org/10.1016/j.molstruc.2014.04.003
---------- CHICAGO ----------
Raffo, P.A., Rossi, L., Alborés, P., Baggio, R.F., Cukiernik, F.D. "Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures" . Journal of Molecular Structure 1070, no. 1 (2014) : 86-93.
http://dx.doi.org/10.1016/j.molstruc.2014.04.003
---------- MLA ----------
Raffo, P.A., Rossi, L., Alborés, P., Baggio, R.F., Cukiernik, F.D. "Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures" . Journal of Molecular Structure, vol. 1070, no. 1, 2014, pp. 86-93.
http://dx.doi.org/10.1016/j.molstruc.2014.04.003
---------- VANCOUVER ----------
Raffo, P.A., Rossi, L., Alborés, P., Baggio, R.F., Cukiernik, F.D. Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures. J. Mol. Struct. 2014;1070(1):86-93.
http://dx.doi.org/10.1016/j.molstruc.2014.04.003