Synthesis, characterization, and thermochemistry of adducts of zinc, cadmium and mercury halides with N,N-dimethylformamide

Oliveira, Ótom Anselmo de; Chagas, Aécio P.; Airoldi, Cláudio

doi:10.1021/ic00143a030

Cited by 32 publications

(6 citation statements)

References 2 publications

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“…This postulation was subsequently confirmed from the single-crystal structure of 18 (see X-ray discussion). The CO stretching vibration of free DMF at 1678 cm -1 shifts to a lower frequency at around 1650 cm -1 (ν ∆(CO) = ∼ 30 cm -1 ) in compounds 19 and 20, which has been ascribed to the coordination of the oxygen atom of DMF to mercury [57,58]. 19) appeared at around 9.0 ppm followed by a signal at around 8.95 ppm due to H-9, while a reverse trend was noted for the heterobimetallic compounds (17 and 20).…”

Section: Infrared Nmr Spectra and Photophysical Propertiesmentioning

confidence: 99%

An organomercury enzyme activator as a versatile template for new organomercury(II) compounds encompassing homobimetallic (RHg/Hg) and heterobimetallic (RHg/Cd) compositions: Syntheses, photoluminescence and structures

Baul

Longkumer

Linden

2014

Journal of Organometallic Chemistry

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A series of pale yellow imine-functionalized acetyloxy(4-(arylideneamino)phenyl)mercury(II) compounds (2-7) were obtained by the reactions of acetyloxy(4-aminophenyl)mercury(II) (1) with arylaldehydes in equimolar ratios in absolute ethanol under reflux conditions. Organomercury compounds 2-5 and 7, when treated with 1,5-diphenylthiocarbazone (dptc) in chloroform, formed dark-red (4-((E)-arylideneamino)phenyl)(((Z)-((E)-phenyldiazenyl) (2-phenylhydrazono)methyl)thio)mercury compounds (8e12) in alkaline medium. The reaction of 7 with a slight excess of mercuric chloride in anhydrous methanol led to the formation of the bimetallic compound (2-[4-(acetyloxymercuryl) This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT[ Construction of mono-and a bi-metallic organomercury/mercury and organomercury/cadmium compounds were accomplished from an enzyme activator via suitably designed imine-functionalized organomercury ligand. M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT

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Section: Infrared Nmr Spectra and Photophysical Propertiesmentioning

confidence: 99%

An organomercury enzyme activator as a versatile template for new organomercury(II) compounds encompassing homobimetallic (RHg/Hg) and heterobimetallic (RHg/Cd) compositions: Syntheses, photoluminescence and structures

Baul

Longkumer

Linden

2014

Journal of Organometallic Chemistry

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“…was prepared according to the procedure reported by de Oliveira et al 15 To a flame-dried 100-mL flask with stir bar was added ZnCl2 (1.4 g, 10 mmol, 1.0 equiv), DMF (25 mL, 0.40 M), and the reaction was stirred at room temperature overnight. The reaction was then concentrated to yield the product as a white solid (2.5 g, 8.7 mmol, 87%).…”

Section: Zncl2•2dmfmentioning

confidence: 99%

“…Our group recently reported that cyclopropanols react with amines in the presence of Zn(II) to yield cyclopropylamines, via trapping of a zinc homoenolate intermediate. 14,15 Inspired by the contributions of Matsubara and Walsh, we wondered if trans-cyclopropylamines could be accessed from αchloroaldehydes 16 and CH2(ZnI)2 by trapping the intermediate zinc homoenolate with an amine (Scheme 1b, grey box). Herein we report the…”

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confidence: 99%

Synthesis of trans-2-Substituted Cyclopropylamines from α-Chloroaldehydes

et al. 2019

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Cyclopropylamines are prevalent motifs in pharmaceuticals and agrochemicals. Herein, we report the synthesis of trans-2-substituted-cyclopropylamines in high diastereoselectivity from readily available α-chloroaldehydes. The reaction proceeds via trapping of an electrophilic zinc homoenolate with an amine followed by ring-closure to generate the cyclopropylamine product. We have also observed that cis/trans-isomerization of the cyclopropylamine can occur in the presence of zinc halide salts and that this process can be turned off by the addition of a polar aprotic co-solvent to the reaction. File list (2) download file view on ChemRxiv Rousseaux-Cyclopropylamines-Manuscript ChemRxiv... (392.68 KiB) download file view on ChemRxiv Rousseaux-Cyclopropylamines-SI ChemRxiv.pdf (3.16 MiB)

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“…As in previous works [4][5][6] , the adducts with dimetylformamide (dmf) and the zinc group halides 7,8 were used as models to obtain the empirical equations, but with no special reasons to do this, only by a question of choice.…”

Section: Obtainning the Equationsmentioning

confidence: 99%

“…The γ values for adducts with 1 and 2 ligands were obtained using the thermogravimetric and calorimetric data for dmf and zinc group halides adducts 7,8 . The γ values for adducts with 3 ligands were obtained by extrapolation, assuming that, the increase (in percentage) in the value of γ from 2 to 3 ligands, is the same that is observed from 1 to 2 ligands.…”

Section: Obtainning the Equationsmentioning

confidence: 99%

Estimating the value of the metal-ligand bond dissociation enthalpy<D> (M-L) for adducts using empirical equations supported by TG data

Farias¹

1999

Quím. Nova

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Recebido em 11/12/97; aceito em 10/11/98In this work is presented and tested (for 106 adducts, mainly of the zinc group halides) two empirical equations supported in TG data to estimate the value of the metal-ligand bond dissociation enthalpy for adducts: (M-O) = ti / γ if ti < 420 K and (M-O) = (ti / γ ) -7,75 . 10 -2 . ti if t i > 420 K. In this empirical equations, ti is the thermodynamic temperature of the beginning of the thermal decomposition of the adduct, as determined by thermogravimetry, and γ is a constant factor that is function of the metal halide considered and of the number of ligands, but is not dependant of the ligand itself. To half of the tested adducts the difference between experimental and calculated values was less than 5%. To about 80% of the tested adducts, the difference between the experimental (calorimetric) and the calculated (using the proposed equations) values are less than 15%.

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Synthesis, characterization, and thermochemistry of adducts of zinc, cadmium and mercury halides with N,N-dimethylformamide

Cited by 32 publications

References 2 publications

An organomercury enzyme activator as a versatile template for new organomercury(II) compounds encompassing homobimetallic (RHg/Hg) and heterobimetallic (RHg/Cd) compositions: Syntheses, photoluminescence and structures

An organomercury enzyme activator as a versatile template for new organomercury(II) compounds encompassing homobimetallic (RHg/Hg) and heterobimetallic (RHg/Cd) compositions: Syntheses, photoluminescence and structures

Synthesis of trans-2-Substituted Cyclopropylamines from α-Chloroaldehydes

Estimating the value of the metal-ligand bond dissociation enthalpy<D> (M-L) for adducts using empirical equations supported by TG data

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Synthesis, characterization, and thermochemistry of adducts of zinc, cadmium and mercury halides with N,N-dimethylformamide

Cited by 32 publications

References 2 publications

An organomercury enzyme activator as a versatile template for new organomercury(II) compounds encompassing homobimetallic (RHg/Hg) and heterobimetallic (RHg/Cd) compositions: Syntheses, photoluminescence and structures

An organomercury enzyme activator as a versatile template for new organomercury(II) compounds encompassing homobimetallic (RHg/Hg) and heterobimetallic (RHg/Cd) compositions: Syntheses, photoluminescence and structures

Synthesis of trans-2-Substituted Cyclopropylamines from α-Chloroaldehydes

Estimating the value of the metal-ligand bond dissociation enthalpy&lt;D&gt; (M-L) for adducts using empirical equations supported by TG data

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Estimating the value of the metal-ligand bond dissociation enthalpy<D> (M-L) for adducts using empirical equations supported by TG data