Supramolecular Packing of a Series of N-Phenylamides and the Role of NH···O=C Interactions
[Image: see text] A series of seven N-phenylamides [R–C(O)NHPh, in which R: CH(3), C(CH(3))(3), Ph, CF(3), CCl(3), CBr(3), and H] were used as models in this study. Molecular packing and intermolecular interactions were evaluated by theoretical calculations, solution NMR, and quantum theory of atoms...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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American Chemical Society
2018
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6645157/ https://www.ncbi.nlm.nih.gov/pubmed/31458083 http://dx.doi.org/10.1021/acsomega.8b01801 |
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author | Pagliari, Anderson B. Orlando, Tainára Salbego, Paulo R. S. Zimmer, Geórgia C. Hörner, Manfredo Zanatta, Nilo Bonacorso, Helio G. Martins, Marcos A. P. |
author_facet | Pagliari, Anderson B. Orlando, Tainára Salbego, Paulo R. S. Zimmer, Geórgia C. Hörner, Manfredo Zanatta, Nilo Bonacorso, Helio G. Martins, Marcos A. P. |
author_sort | Pagliari, Anderson B. |
collection | PubMed |
description | [Image: see text] A series of seven N-phenylamides [R–C(O)NHPh, in which R: CH(3), C(CH(3))(3), Ph, CF(3), CCl(3), CBr(3), and H] were used as models in this study. Molecular packing and intermolecular interactions were evaluated by theoretical calculations, solution NMR, and quantum theory of atoms in molecules analyses. Crystallization mechanisms were proposed based on the energetic and topological parameters using the supramolecular cluster as demarcation. Concentration-dependent (1)H NMR experiments corroborated the proposed interactions between molecules. For all compounds (except for R: H, which initially formed tetramers), layers (two-dimensional) or chains (one-dimensional) were formed in the first stage of the proposed crystallization mechanisms. The presence of strong intermolecular NH···O=C interactions promoted the first stages. The study in solution provided different values of association constant (K(ass)) governed by the hydrogen bond NH···O=C, showing that the stronger interactions are directly influenced by the substituent steric hindrance. A correlation between K(ass(NH···O=C)) from the solution and the NH···O=C interaction energy in the crystal showed a good trend. |
format | Online Article Text |
id | pubmed-6645157 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-66451572019-08-27 Supramolecular Packing of a Series of N-Phenylamides and the Role of NH···O=C Interactions Pagliari, Anderson B. Orlando, Tainára Salbego, Paulo R. S. Zimmer, Geórgia C. Hörner, Manfredo Zanatta, Nilo Bonacorso, Helio G. Martins, Marcos A. P. ACS Omega [Image: see text] A series of seven N-phenylamides [R–C(O)NHPh, in which R: CH(3), C(CH(3))(3), Ph, CF(3), CCl(3), CBr(3), and H] were used as models in this study. Molecular packing and intermolecular interactions were evaluated by theoretical calculations, solution NMR, and quantum theory of atoms in molecules analyses. Crystallization mechanisms were proposed based on the energetic and topological parameters using the supramolecular cluster as demarcation. Concentration-dependent (1)H NMR experiments corroborated the proposed interactions between molecules. For all compounds (except for R: H, which initially formed tetramers), layers (two-dimensional) or chains (one-dimensional) were formed in the first stage of the proposed crystallization mechanisms. The presence of strong intermolecular NH···O=C interactions promoted the first stages. The study in solution provided different values of association constant (K(ass)) governed by the hydrogen bond NH···O=C, showing that the stronger interactions are directly influenced by the substituent steric hindrance. A correlation between K(ass(NH···O=C)) from the solution and the NH···O=C interaction energy in the crystal showed a good trend. American Chemical Society 2018-10-22 /pmc/articles/PMC6645157/ /pubmed/31458083 http://dx.doi.org/10.1021/acsomega.8b01801 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Pagliari, Anderson B. Orlando, Tainára Salbego, Paulo R. S. Zimmer, Geórgia C. Hörner, Manfredo Zanatta, Nilo Bonacorso, Helio G. Martins, Marcos A. P. Supramolecular Packing of a Series of N-Phenylamides and the Role of NH···O=C Interactions |
title | Supramolecular Packing of a Series of N-Phenylamides
and the Role of NH···O=C
Interactions |
title_full | Supramolecular Packing of a Series of N-Phenylamides
and the Role of NH···O=C
Interactions |
title_fullStr | Supramolecular Packing of a Series of N-Phenylamides
and the Role of NH···O=C
Interactions |
title_full_unstemmed | Supramolecular Packing of a Series of N-Phenylamides
and the Role of NH···O=C
Interactions |
title_short | Supramolecular Packing of a Series of N-Phenylamides
and the Role of NH···O=C
Interactions |
title_sort | supramolecular packing of a series of n-phenylamides
and the role of nh···o=c
interactions |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6645157/ https://www.ncbi.nlm.nih.gov/pubmed/31458083 http://dx.doi.org/10.1021/acsomega.8b01801 |
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