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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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00222860_v1070_n1_p86_Raffo |
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todo:paper_00222860_v1070_n1_p86_Raffo2023-10-03T14:30:30Z Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures Raffo, P.A. Rossi, L. Alborés, P. Baggio, R.F. Cukiernik, F.D. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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, 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 |
| 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. |
| format |
JOUR |
| author |
Raffo, P.A. Rossi, L. Alborés, P. Baggio, R.F. Cukiernik, F.D. |
| author_facet |
Raffo, P.A. Rossi, L. Alborés, P. Baggio, R.F. Cukiernik, F.D. |
| author_sort |
Raffo, P.A. |
| 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 |
| url |
http://hdl.handle.net/20.500.12110/paper_00222860_v1070_n1_p86_Raffo |
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