Multiple Noncovalent Binding in the Intermediates and Products of the Reaction of N,N-Dimethylformamide with Bromine

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Abstract

Reaction of nonionic N,N-dimethylformamide (DMF) with bromine under controllable conditions leads to a number of ionic compounds, mainly to bis(N,N-dimethylformamide)hydrogen dibromobromate. Computations with DFT (ωB97xV/dgdzvp) were made for geometry, thermochemistry and electron configuration of products and supposed intermediates. Two labile particles [bis(N,N-dimethylformamide)hydrogen cation and dibromobromate-anion] form stable highly conductive ionic liquid that can be distilled in vacuo without losses or decomposition. A number of molecular complexes of DMF with bromine and water presumed to be intermediates of this reaction. It is a set of halogen and hydrogen bonding that provide an intramolecular binding in these complexes.

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About the authors

O. M. Zarechnaya

L. M. Litvinenko Institute of Physical Organic and Coal Chemistry

Email: v_mikhailov@yahoo.com
Russian Federation, Donetsk

V. A. Mikhailov

L. M. Litvinenko Institute of Physical Organic and Coal Chemistry

Author for correspondence.
Email: v_mikhailov@yahoo.com
ORCID iD: 0000-0002-4184-1805
Russian Federation, Donetsk

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Supplementary files

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2. Scheme 1

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3. Fig. 1. Binary complexes of DMFA with bromine

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4. Fig. 2. Triple complexes of DMFA with bromine of stoichiometry 1:2 and 2:1

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5. Fig. 3. Binary complexes of DMFA with hydrogen bromide

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6. Fig. 4. Complexes of DMFA with water

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7. Fig. 5. Mixed-ligand ternary complexes of DMFA with water and bromine

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8. Fig. 6. General view of ternary complexes DMFA-Br2-Br-

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9. Fig. 7. General view of the molecule of the putative ionic intermediates XXI-XXIII

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10. Fig. 8. General view of cations as reaction products

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11. Scheme 2

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