Author | Silva Jr., Floriano P. | |
Author | Ellena, Javier | |
Author | Ferreira, Marcelle de Lima | |
Author | Mascarenhas, Yvonne P. | |
Author | Souza, Marcus V. N. de | |
Author | Vasconcelos, Thatyana R. A. | |
Author | Wardell, James L. | |
Author | Wardell, Solange M. S. V. | |
Access date | 2020-02-04T11:07:35Z | |
Available date | 2020-02-04T11:07:35Z | |
Document date | 2006 | |
Citation | SILVA JR., Floriano P. et al. Experimental and theoretical structure characterization of two isoniazid derivatives: 2,4-Difluoro-N0-isonicotinoylbenzohydrazide and 2,4-dichloro-N0-isonicotinoylbenzohydrazide hydrochloride. Journal of Molecular Structure, v. 788, p. 63-71, 2006. | pt_BR |
ISSN | 0022-2860 | pt_BR |
URI | https://www.arca.fiocruz.br/handle/icict/39690 | |
Language | eng | pt_BR |
Publisher | Elsevier | pt_BR |
Rights | restricted access | pt_BR |
Subject in Portuguese | Derivados de isoniazida | pt_BR |
Subject in Portuguese | Estrutura de raios X | pt_BR |
Subject in Portuguese | Cálculo da supermolécula | pt_BR |
Subject in Portuguese | Teoria da densidade funcional | pt_BR |
Subject in Portuguese | Superfícies de energia potencial | pt_BR |
Subject in Portuguese | Energia eletrônica | pt_BR |
Title | Experimental and theoretical structure characterization of two isoniazid derivatives: 2,4-Difluoro-N0-isonicotinoylbenzohydrazide and 2,4-dichloro-N0-isonicotinoylbenzohydrazide hydrochloride | pt_BR |
Type | Article | pt_BR |
DOI | 10.1016/j.molstruc.2005.11.023 | |
Abstract | An X-ray and a theoretical study of the structure of the isoniazid derivatives, 2,4-difluoro-N0-isonicotinoylbenzohydrazide, 3, and 2,4-dichloro-
N0-isonicotinoylbenzohydrazide hydrochloride, [4HC, ClK, 2(H2O)], are reported. Quantum chemical calculations as well as conformational
analysis are presented with the isolated cations [3HC] and [4HC], where the former was protonated in silico to allow direct comparison of results.
Supermolecule calculations were also carried out with the asymmetric unit of [4HC, ClK, 2(H2O)], which is comprised of two independent cations
(4HC), two chloride ions and four water molecules. Our results indicate that the crystal structures, although clearly representing accessible
conformations, are highly distorted in comparison to the predicted lower energy conformers in the gas-phase. These distortions are most probably
imposed by polar and electrostatic interactions within the crystal packing. In general, the calculated potential energy surfaces (PES) for both
isoniazid derivatives are fairly flat, a feature confirmed by the low energetic difference calculated for several conformers corresponding to local
minima in PES. Noteworthy, the fluorinated compound [3HC] shows an important additional energy barrier for rotation around the bond
connecting the halogenated ring to the proximate carbonyl due to a strong internal hydrogen bond involving the fluorine atom. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Bioquímica de Proteínas e Peptídeos. Rio de Janeiro, RJ, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Química. Rio de Janeiro, RJ, Brasil. | pt_BR |
Affilliation | Universidade de São Paulo. Instituto de Física de São Carlos. São Carlos, SP, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Far-Manguinhos. Rio de Janeiro, RJ, Brasil. | pt_BR |
Affilliation | Universidade de São Paulo. Instituto de Física de São Carlos. São Carlos, SP, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Far-Manguinhos. Rio de Janeiro, RJ, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Far-Manguinhos. Rio de Janeiro, RJ, Brasil. | pt_BR |
Affilliation | Universidade Federal do Rio de Janeiro. Instituto de Química. Rio de Janeiro, RJ, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Far-Manguinhos. Rio de Janeiro, RJ, Brasil. | pt_BR |
Subject | Isoniazid derivatives | pt_BR |
Subject | X-ray structure | pt_BR |
Subject | Supermolecule calculation | pt_BR |
Subject | Density functional theory | pt_BR |
Subject | RHF | pt_BR |
Subject | Potential energy surfaces | pt_BR |
Subject | Electronic energy | pt_BR |
Embargo date | 2025-01-01 | |