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Quantitative structure-retention relationships of antimicrobial hydrazides evaluated by reverse-phase liquid chromatography

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Summary

Quantitative structure-retention relationships of antimicrobial hydrazides were investigated by reversedphase liquid chromatography (RPLC), to disclose retention mechanisms operating in a C-8 column. Capacity factors (logk) were obtained using methanol-water mobile phase in volume fractions: 25–75%v/v. Extrapolated logk w values were derived from logk versus mobile phase, volume fraction of organic modifier, φ, using logk=logk w −Sφ. The chemical validity of a linear relationship between the slopes (S) and intercepts (logk w ) was established.S-logk w correlations are chemically meaningful for a non-homologous series of compounds. The existence of a clear separation of hydrazides into two different sets of hydrogen-bonding capabilities demonstrated the role of such relationships. Standard CoMFA fields were used to delineate those specific intermolecular interactions responsible for changes in retention of study hydrazides. Thus, a 3D QSAR (CoMFA) model showed thatS exhibits electrostatic behaviour towards a C-8 HPLC column.

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Authors and Affiliations

  1. Núcleo de Estudos em Química Medicinal-NEQUIM, Departamento de Química, Universidade Federal de Minas Gerais, Campus da Pampulha, 31270-901, Belo Horizonte, MG, Brazil

    M. L. C. Montanari & C. A. Montanari

  2. Departamento de Química, Universidade Federal de São Carlos, Rodovia Washington Luis, São Carlos, SP, Brazil

    Q. B. Cass

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  1. M. L. C. Montanari
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  2. Q. B. Cass
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  3. C. A. Montanari
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Montanari, M.L.C., Cass, Q.B. & Montanari, C.A. Quantitative structure-retention relationships of antimicrobial hydrazides evaluated by reverse-phase liquid chromatography. Chromatographia 51, 722–726 (2000). https://doi.org/10.1007/BF02505411

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