Determination of the tautomerism of albendazole desmotropes using solution and solid state NMR together with DFT theoretical calculations, both energies and chemical shifts

Claramunt, R. M.; López, Concepcíon; Sanz, Dionísia; Elguero, José; Alkorta, Ibón

doi:10.1016/j.molstruc.2022.132883

Cited by 6 publications

(5 citation statements)

References 53 publications

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“…Its geometries were optimized using the B3LYP functional with the Pople basis set 6-31G(d) [37] and the solvent (DMSO) was taken into account in the PCM approach in the calculations of 13 C chemical shifts. A very good fit was obtained between calculated and experimental 13 C chemical shifts; R 2 = 0.9949 for structure A. Albendazole may exist both as tautomers and rotamers, as shown in Figure 14 [33]. As seen, the interplay of a very complex set of structures may occur.…”

Section: Tautomerismmentioning

confidence: 64%

“…Albendazole may exist both as tautomers and rotamers, as shown in Figure 14 [ 33 ]. As seen, the interplay of a very complex set of structures may occur.…”

Section: Resultsmentioning

confidence: 99%

“…The calculated 13 C chemical shifts form a good base for further studies [32]. Albendazole may exist both as tautomers and rotamers, as shown in Figure 14 [33]. As seen, the interplay of a very complex set of structures may occur.…”

Section: Tautomerismmentioning

confidence: 92%

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The Synergy between Nuclear Magnetic Resonance and Density Functional Theory Calculations

Hansen

2024

Molecules

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This paper deals with the synergy between Nuclear Magnetic Resonance (NMR) spectroscopic investigations and DFT calculations, mainly of NMR parameters. Both the liquid and the solid states are discussed here. This text is a mix of published results supplemented with new findings. This paper deals with examples in which useful results could not have been obtained without combining NMR measurements and DFT calculations. Examples of such cases are tautomeric systems in which NMR data are calculated for the tautomers; hydrogen-bonded systems in which better XH bond lengths can be determined; cage compounds for which assignment cannot be made based on NMR data alone; revison of already published structures; ionic compounds for which reference data are not available; assignment of solid-state spectra and crystal forms; and the creation of libraries for biological molecules. In addition to these literature cases, a revision of a cage structure and substituent effects on pyrroles is also discussed.

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Section: Tautomerismmentioning

confidence: 64%

“…Albendazole may exist both as tautomers and rotamers, as shown in Figure 14 [ 33 ]. As seen, the interplay of a very complex set of structures may occur.…”

Section: Resultsmentioning

confidence: 99%

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The Synergy between Nuclear Magnetic Resonance and Density Functional Theory Calculations

Hansen

2024

Molecules

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“…Wojtulewski et al 141 used 13 C CP MAS NMR and DFT calculations in studies of 6-chromanyl derivatives. Alkorta et al 142 reported on determination of the tautomerism of albendazole desmotropes using solution and solid state NMR combined with DFT prediction of energy and chemical shifts.…”

Section: Nuclear Shielding Calculation In Natural Productsmentioning

confidence: 99%

Theory and computation of nuclear shielding

2023

Nuclear Magnetic Resonance

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This chapter continues earlier reviews of essential works on theoretical issues of nuclear magnetic shieldings published from 1 January to 31 December 2022. As previously, the chapter concentrates on theoretical calculations of nuclear shielding parameters and/or chemical shifts in case of free molecules in the gas phase and solution, and in some cases in the solid state using a periodic formulation. The nuclear shieldings in solution are mainly calculated using inexpensive polarizable continuum model of solvent (PCM). The use of discrete solvent molecules (in particular water and other polar solvents), which is essential for correct description of hydrogen bonding, is often omitted by numerous authors. Most calculations use a relatively simple and fast, but reliable density functional theory (DFT) combined with gauge-including atomic orbital (GIAO) approach. On the other hand, reports on prediction of nuclear magnetic shielding parameters using high level theoretical methods combined with large and flexible basis sets are not so common due to the enormous computational cost. In addition, correction of raw theoretical nuclear magnetic shieldings due to ro-vibration (zero-point vibration correction, ZPVC) and temperature corrections (TC), as well as implicit and explicit solvent effects and relativistic corrections are not often reported.

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“…Por exemplo, a alguns detalhes envolvendo equilíbrio tautomérico, por parte das espécies envolvidas, foi dada uma atenção especial, especialmente devido à estrutura desses compostos propiciar esse tipo de equilíbrio, podendo assim gerar mais de uma espécie reativa e exercer alguma participação no processo reacional. (146) Os organocatalisadores utilizados estão representados abaixo. Outras possibilidades foram testadas, porém os resultados mais relevantes se deram com os catalisadores citados (Figura 37).…”

Section: Organocatalisadores Para Bromociclização Assimétricaunclassified

Estudo de reações catalíticas por espectroscopia de ação e mobilidade iônica acopladas à espectrometria de massas

Ribeiro¹

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A elaboração desta tese envolveu a contribuição de muitas pessoas sem as quais a realização desta pesquisa seria impossível. A todos que, direta e indiretamente, contribuíram para realização deste trabalho, meu muito obrigado. Aos meus primeiros mestres, meus pais Otávio e Dejanira. Aos meus irmãos, Washington, Wellington e Alexandra por acreditarem em mim. À minha namorada, Alana Maria, por todo o apoio ao longo desses anos, e por toda a sua paciência. Ao Prof. Dr. Thiago Carita Correra, pela paciência do orientador, pela competência do pesquisador, exemplos para mim. Ao Prof. Dr. Scott J. McIndoe, por todo o auxílio e ensinamentos. Ao Prof. Dr. Alessandro Rodrigues, pelo suporte que foi fundamental para que esta tese se tornasse possível. Aos meus colegas do Laboratório MCPL, especialmente minha grande amiga Sharla, pelas conversas estimuladoras e amizade. A todos os meus colegas do laboratório do prof. McIndoe, por toda a ajuda e por tornarem o ambiente receptivo. À Universidade de São Paulo (USP), pela oportunidade de realizar esta pesquisa em suas dependências.À University of Victoria (Uvic), pela infraestrutura utilizada em parte da presente pesquisa.

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Determination of the tautomerism of albendazole desmotropes using solution and solid state NMR together with DFT theoretical calculations, both energies and chemical shifts

Cited by 6 publications

References 53 publications

The Synergy between Nuclear Magnetic Resonance and Density Functional Theory Calculations

The Synergy between Nuclear Magnetic Resonance and Density Functional Theory Calculations

Theory and computation of nuclear shielding

Estudo de reações catalíticas por espectroscopia de ação e mobilidade iônica acopladas à espectrometria de massas

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