Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures

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...

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Autores principales:	Raffo, Pablo Alejandro, Albores, Pablo, Cukiernik, Fabio Daniel
Publicado:	2014
Materias:	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 Benzoic acid
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v1070_n1_p86_Raffo http://hdl.handle.net/20.500.12110/paper_00222860_v1070_n1_p86_Raffo
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00222860_v1070_n1_p86_Raffo
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spelling	paper:paper_00222860_v1070_n1_p86_Raffo2023-06-08T14:48:49Z Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures Raffo, Pablo Alejandro Albores, Pablo Cukiernik, Fabio Daniel 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 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. Fil:Raffo, P.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Alborés, P. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Cukiernik, F.D. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2014 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v1070_n1_p86_Raffo http://hdl.handle.net/20.500.12110/paper_00222860_v1070_n1_p86_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 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
spellingShingle	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 Raffo, Pablo Alejandro Albores, Pablo Cukiernik, Fabio Daniel Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures
topic_facet	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
description	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.
author	Raffo, Pablo Alejandro Albores, Pablo Cukiernik, Fabio Daniel
author_facet	Raffo, Pablo Alejandro Albores, Pablo Cukiernik, Fabio Daniel
author_sort	Raffo, Pablo Alejandro
title	Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures
title_short	Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures
title_full	Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures
title_fullStr	Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures
title_full_unstemmed	Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures
title_sort	alkoxy-benzoic acids: some lacking structures and rationalization of the molecular features governing their crystalline architectures
publishDate	2014
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v1070_n1_p86_Raffo http://hdl.handle.net/20.500.12110/paper_00222860_v1070_n1_p86_Raffo
work_keys_str_mv	AT raffopabloalejandro alkoxybenzoicacidssomelackingstructuresandrationalizationofthemolecularfeaturesgoverningtheircrystallinearchitectures AT alborespablo alkoxybenzoicacidssomelackingstructuresandrationalizationofthemolecularfeaturesgoverningtheircrystallinearchitectures AT cukiernikfabiodaniel alkoxybenzoicacidssomelackingstructuresandrationalizationofthemolecularfeaturesgoverningtheircrystallinearchitectures
_version_	1768542773673197568

Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures

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