Please use this identifier to cite or link to this item:
https://hdl.handle.net/10316/18066
DC Field | Value | Language |
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dc.contributor.author | Fonseca, A. C. | - |
dc.contributor.author | Jarmelo, S. | - |
dc.contributor.author | Carvalho, R. A. | - |
dc.contributor.author | Fausto, R. | - |
dc.contributor.author | Gil, M. H. | - |
dc.contributor.author | Simões, P. N. | - |
dc.date.accessioned | 2012-01-02T10:43:12Z | - |
dc.date.available | 2012-01-02T10:43:12Z | - |
dc.date.issued | 2010-04 | - |
dc.identifier.uri | https://hdl.handle.net/10316/18066 | - |
dc.description.abstract | The molecular structure of the l-arginine derivative, Nα-benzoyl-l-argininate ethyl ester chloride (BAEEH+·Cl−), was characterized by combining quantum chemical methods and 1H NMR spectroscopy. A conformational search on the potential energy surfaces of the three lowest-energy tautomers of BAEEH+ [A: R−N+H═(NH2)2; B: R−NH−C(═NH)N+H3; C: R−N+H2−C(═NH)NH2; R = C6H5C(═O)NH−CH(COOCH2CH3)CH2CH2CH2−] was carried out using the semiempirical PM3 method. The lowest-energy conformations obtained using this method were then optimized at the DFT(B3LYP)/6-31++G(d,p) level of theory. For all tautomers, it was found that all low-energy conformers present folded structures, in which a H-bond interaction between the guanidinium group and the amide carbonyl oxygen atom appears to be the most relevant stabilizing factor. 1H NMR spectra of BAEEH+·Cl− in DMF-D7 were acquired in the temperature range [−55 to 75 °C], providing information about the rotational motions in the guanidinium group and showing that the tautomeric form of BAEEH+ that exists in solution is tautomer A. The interpretation of the experimental findings was supported by 1H NMR chemical shifts obtained theoretically at the DFT(B3LYP)/6-31++G(d,p) level of approximation, using both the polarized continuum model and a BAEEH+−water complex model. | por |
dc.language.iso | eng | por |
dc.publisher | American Chemical Society | por |
dc.rights | openAccess | por |
dc.title | 1H NMR Spectroscopic and Quantum Chemical Studies on a Poly(ester amide) Model Compound: Nα-Benzoyl-l-Argininate Ethyl Ester Chloride. Structural Preferences for the Isolated Molecule and in Solution | por |
dc.type | article | por |
degois.publication.firstPage | 6156 | por |
degois.publication.lastPage | 6164 | por |
degois.publication.title | J. Phys. Chem. B, | por |
dc.peerreviewed | Yes | por |
dc.identifier.doi | 10.1021/jp9114749 | - |
degois.publication.volume | 114 | por |
uc.controloAutoridade | Sim | - |
item.fulltext | Com Texto completo | - |
item.grantfulltext | open | - |
item.languageiso639-1 | en | - |
item.cerifentitytype | Publications | - |
item.openairetype | article | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
crisitem.author.dept | Universidade de Coimbra | - |
crisitem.author.parentdept | Institute of Interdisciplinary Research | - |
crisitem.author.researchunit | CEMMPRE - Centre for Mechanical Engineering, Materials and Processes | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.researchunit | CIEPQPF – Chemical Process Engineering and Forest Products Research Centre | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.orcid | 0000-0002-7145-2472 | - |
crisitem.author.orcid | 0000-0001-5771-458X | - |
crisitem.author.orcid | 0000-0002-8264-6854 | - |
crisitem.author.orcid | 0000-0002-5068-950X | - |
Appears in Collections: | FCTUC Química - Artigos em Revistas Internacionais |
Files in This Item:
File | Description | Size | Format | |
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J.Physical Chemistry B, 114 (2010) 6156.pdf | 279.6 kB | Adobe PDF | View/Open |
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