Conformational dynamics of 4-formylaminoantipyrine based on NMR and theoretical calculations

Author(s)

Silva, Simone Cavalcante ^[1] ; Rodrigues, Shirley M. M. ^[1] ; Nardini, Viviani ^[1] ; Vaz, Artur De L. L. ^[2] ; Palaretti, Vinicius ^[1] ; Jose da Silva, Gil Valdo ^[1] ; Vessecchi, Ricardo ^[1] ; Clososki, Giuliano C. ^{[1, 2]}

Affiliation

^[1] Univ Sao Paulo, Fac Filosofia Ciencias & Letras Ribeirao Preto, Dept Quim, Av Bandeirantes, 3900 Bairro Monte Alegre, BR-14040901 Ribeirao Preto, SP - Brazil

^[2] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Nucleo Pesquisas Prod Nat & Sintet, Av Cafe S-N, BR-14040903 Ribeirao Preto, SP - Brazil

• Document type: Journal article
• Source: Journal of Molecular Structure; v. 1163, p. 280-286, JUL 5 2018.
• Web of Science Citations: 2

Abstract

We investigated the metamizole metabolite 4-formylaminoantipyrine (4-FAA) by H-1 dynamic nuclear magnetic resonance. 4-FAA exhibits a carbon-nitrogen partial double bond that rotates slowly enough, on a resonance time scale, to provide the simultaneous spectra of two rotamers. We examined various solvents in an attempt to understand how protic and aprotic environments influence the anti and syn rotamer equilibriums. Moreover, we compared experimental data and theoretical calculations to evaluate the thermodynamic parameters of the rotational process. (C) 2018 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 15/12811-9 - DIRECTED FUNCTIONALIZATION OF ARENES AND HETEROARENES AIMIMNG THE SYNTHESIS OF SUBSTANCES OF MEDICINAL INTEREST
• Grantee: Giuliano Cesar Clososki
• Support Opportunities: Regular Research Grants
• FAPESP's process: 14/23604-1 - Computational chemistry: a tool to studies of mass spectrometry, reactivity and fragmentation/reaction mechanisms of organic compounds
• Grantee: Ricardo Vessecchi Lourenço
• Support Opportunities: Regular Research Grants