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dc.contributor.author
Valdo, Ana Karoline Silva Mendanha
dc.contributor.author
Sarotti, Ariel Marcelo
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dc.contributor.author
Martins, Felipe T.
dc.date.available
2018-07-26T23:45:16Z
dc.date.issued
2017-09
dc.identifier.citation
Valdo, Ana Karoline Silva Mendanha; Sarotti, Ariel Marcelo; Martins, Felipe T.; Synthon trends according to acid strength and geometry in salts of N-heterocyclic bases; Royal Society of Chemistry; CrystEngComm; 19; 40; 9-2017; 5960-5965
dc.identifier.issn
1466-8033
dc.identifier.uri
http://hdl.handle.net/11336/53277
dc.description.abstract
The hierarchy and robustness of homosynthons and heterosynthons formed by N-heterocyclic bases were assessed experimentally in salts of aminopyrazine (ampyz) and trans-1,2-bis(4-pyridyl)ethane (BPE) with common strong, moderate and weak acids, and theoretically at the M06-2X/6-31+G∗∗ level of theory. A trend for a base-pairing primary homosynthon to assemble in ampyz salts as the acid strength increases can be drawn. This homosynthon is present in chloride and bromide salts of ampyz, which is compatible with protonation at N4 and the formation of an accessory four-point heterosynthon engaging two (ampyz)+ cations and two halides. This robust synthon is also present in chloride, bromide and dihydrogen phosphate salts of BPE. Among all our BPE multicomponent crystal forms, it is not found only in the uncommon phosphoric acid cocrystal of the dihydrogen phosphate salt. When ampyz was crystallized with weaker acids such as trifluoroacetic, trichloroacetic and phosphoric acids, the primary homosynthon disappears gradually as the strength acid decreases. In the last two cases, this homosynthon is not found, but the trifluoroacetate salt of ampyz is found to have both the base-pairing primary homosynthon and the two-point heterosynthon with carboxylate. Both monoprotonated forms at N1 and N4 are found together in this structure. Another trend of N1 protonation in the presence of counterions from inorganic tetrahedral oxoacids such as isopropyl sulfuric and phosphoric acids is also outlined, regardless of their acid strength.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Royal Society of Chemistry
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dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Salts of N-Heterocyclic Bases
dc.subject
Dft Calculations
dc.subject
Acid Strenght
dc.subject.classification
Otras Ciencias Químicas
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Synthon trends according to acid strength and geometry in salts of N-heterocyclic bases
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2018-07-26T14:01:37Z
dc.journal.volume
19
dc.journal.number
40
dc.journal.pagination
5960-5965
dc.journal.pais
Reino Unido
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dc.journal.ciudad
Cambridge
dc.description.fil
Fil: Valdo, Ana Karoline Silva Mendanha. Universidade Federal de Goiás; Brasil
dc.description.fil
Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
dc.description.fil
Fil: Martins, Felipe T.. Universidade Federal de Goiás; Brasil
dc.journal.title
CrystEngComm
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://dx.doi.org/10.1039/C7CE01490B
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2017/CE/C7CE01490B
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