Curcumin Related 1,4‐Diazepines: Regioselective Synthesis, Structure Analysis, Tautomerism, NMR Spectroscopy, X‐ray Crystallography, Density Functional Theory and GIAO Calculations | Zendy

Nieto Carla I. | Zendy; Andrade Ana | Zendy; Sanz Dionisia | Zendy; Claramunt Rosa M. | Zendy; Torralba M. Carmen | Zendy; Torres M. Rosario | Zendy; Alkorta Ibon | Zendy; Elguero José | Zendy

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Curcumin Related 1,4‐Diazepines: Regioselective Synthesis, Structure Analysis, Tautomerism, NMR Spectroscopy, X‐ray Crystallography, Density Functional Theory and GIAO Calculations

Author(s) -

Nieto Carla I.,

Andrade Ana,

Sanz Dionisia,

Claramunt Rosa M.,

Torralba M. Carmen,

Torres M. Rosario,

Alkorta Ibon,

Elguero José

Publication year - 2017

Publication title -

chemistryselect

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.437

H-Index - 34

ISSN - 2365-6549

DOI - 10.1002/slct.201700405

Subject(s) - tautomer , chemistry , density functional theory , regioselectivity , nuclear magnetic resonance spectroscopy , ethylenediamine , computational chemistry , crystallography , x ray , carbon 13 nmr , stereochemistry , organic chemistry , catalysis , physics , quantum mechanics

The reaction of 1,2‐ethylenediamine with seven fluorinated β‐diketones affords two different 1,4‐diazepine series depending on the experimental conditions. Their structures as well as tautomerism have been established by 1 H, 13 C, 15 N and 19 F nuclear magnetic resonance in solution supported by density functional theory calculations at the B3LYP/6‐311++G(d,p) level. The two compounds obtained from ( E )‐5‐(2‐fluoro‐4‐hydroxyphenyl)‐1‐phenylpent‐4‐ene‐1,3‐dione were analyzed by X‐ray crystallography and studied by solid‐state NMR.

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