N-H⋯O assisted structural changes induced on ketoenamine systems

M. Rodríguez; R. Santillan; Y. López; N. Farfán; V. Barba; K. Nakatani; E. V.García Baéz; I. I. Padilla-Martínez

doi:10.1080/10610270701534778

N-H⋯O assisted structural changes induced on ketoenamine systems

M. Rodríguez, R. Santillan, Y. López, N. Farfán, V. Barba, K. Nakatani, E. V.García Baéz, I. I. Padilla-Martínez

Unidad Profesional Interdisciplinaria de Biotecnología (UPIBI)

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

The tautomeric equilibrium between the ketoenamine and enolimine forms for a series of arylimines (1a-1c) derived from salicylaldehyde and enaminones (2a-2f) derived from benzoylacetone and substituted anilines has been analyzed in solution by 1H NMR and UV-vis spectroscopy, while IR and X-ray diffraction analyses were used in the solid state. The X-ray diffraction analysis of 1a, 2a-2c and 2e-2f showed that the most stable tautomer is the ketoenamine and all enaminones present intramolecular NH⋯O hydrogen bonds forming a six member ring in which the keto form is favored. In addition, the VT-NMR analysis for 2b in solvents of different polarities evidenced the behavior of the tautomeric equilibrium, showing that in DMF and acetone at low temperature, the enolimine tautomer is more stable.

Original language	English
Pages (from-to)	641-653
Number of pages	13
Journal	Supramolecular Chemistry
Volume	19
Issue number	8
DOIs	https://doi.org/10.1080/10610270701534778
State	Published - Dec 2007

Keywords

Enaminones
Imines
RAHB
VT-NMR
X-ray

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10.1080/10610270701534778

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title = "N-H⋯O assisted structural changes induced on ketoenamine systems",

abstract = "The tautomeric equilibrium between the ketoenamine and enolimine forms for a series of arylimines (1a-1c) derived from salicylaldehyde and enaminones (2a-2f) derived from benzoylacetone and substituted anilines has been analyzed in solution by 1H NMR and UV-vis spectroscopy, while IR and X-ray diffraction analyses were used in the solid state. The X-ray diffraction analysis of 1a, 2a-2c and 2e-2f showed that the most stable tautomer is the ketoenamine and all enaminones present intramolecular NH⋯O hydrogen bonds forming a six member ring in which the keto form is favored. In addition, the VT-NMR analysis for 2b in solvents of different polarities evidenced the behavior of the tautomeric equilibrium, showing that in DMF and acetone at low temperature, the enolimine tautomer is more stable.",

keywords = "Enaminones, Imines, RAHB, VT-NMR, X-ray",

author = "M. Rodr{\'i}guez and R. Santillan and Y. L{\'o}pez and N. Farf{\'a}n and V. Barba and K. Nakatani and Ba{\'e}z, {E. V.Garc{\'i}a} and Padilla-Mart{\'i}nez, {I. I.}",

note = "Funding Information: The authors thank CONACyT for financial support and the scholarship to M. Rodriguez. Thanks are given to Consejo Superior de la Investigaci{\'o}n Cient{\'i}fica in Spain for the Cambridge Crystal- lographic Data Base license, to M. L. Rodriguez for NMR spectra, R. Yepez for IR, M. A. Leyva for X-ray analysis and G. Cuellar for MS.",

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doi = "10.1080/10610270701534778",

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volume = "19",

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journal = "Supramolecular Chemistry",

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T1 - N-H⋯O assisted structural changes induced on ketoenamine systems

AU - Rodríguez, M.

AU - Santillan, R.

AU - López, Y.

AU - Farfán, N.

AU - Barba, V.

AU - Nakatani, K.

AU - Baéz, E. V.García

AU - Padilla-Martínez, I. I.

N1 - Funding Information: The authors thank CONACyT for financial support and the scholarship to M. Rodriguez. Thanks are given to Consejo Superior de la Investigación Científica in Spain for the Cambridge Crystal- lographic Data Base license, to M. L. Rodriguez for NMR spectra, R. Yepez for IR, M. A. Leyva for X-ray analysis and G. Cuellar for MS.

PY - 2007/12

Y1 - 2007/12

N2 - The tautomeric equilibrium between the ketoenamine and enolimine forms for a series of arylimines (1a-1c) derived from salicylaldehyde and enaminones (2a-2f) derived from benzoylacetone and substituted anilines has been analyzed in solution by 1H NMR and UV-vis spectroscopy, while IR and X-ray diffraction analyses were used in the solid state. The X-ray diffraction analysis of 1a, 2a-2c and 2e-2f showed that the most stable tautomer is the ketoenamine and all enaminones present intramolecular NH⋯O hydrogen bonds forming a six member ring in which the keto form is favored. In addition, the VT-NMR analysis for 2b in solvents of different polarities evidenced the behavior of the tautomeric equilibrium, showing that in DMF and acetone at low temperature, the enolimine tautomer is more stable.

AB - The tautomeric equilibrium between the ketoenamine and enolimine forms for a series of arylimines (1a-1c) derived from salicylaldehyde and enaminones (2a-2f) derived from benzoylacetone and substituted anilines has been analyzed in solution by 1H NMR and UV-vis spectroscopy, while IR and X-ray diffraction analyses were used in the solid state. The X-ray diffraction analysis of 1a, 2a-2c and 2e-2f showed that the most stable tautomer is the ketoenamine and all enaminones present intramolecular NH⋯O hydrogen bonds forming a six member ring in which the keto form is favored. In addition, the VT-NMR analysis for 2b in solvents of different polarities evidenced the behavior of the tautomeric equilibrium, showing that in DMF and acetone at low temperature, the enolimine tautomer is more stable.

KW - Enaminones

KW - Imines

KW - RAHB

KW - VT-NMR

KW - X-ray

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U2 - 10.1080/10610270701534778

DO - 10.1080/10610270701534778

M3 - Artículo

SN - 1061-0278

VL - 19

SP - 641

EP - 653

JO - Supramolecular Chemistry

JF - Supramolecular Chemistry

IS - 8

ER -

N-H⋯O assisted structural changes induced on ketoenamine systems

Abstract

Keywords

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