Quantum-chemical study of energies of maleimide and itaconimide isomeric derivatives

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Abstract

For 38 pairs of the isomeric derivatives of maleimide and itaconimide, the Gibbs free energies were calculated using the density functional theory (DFT) and domain-based local pair natural orbital (DLPNO) methods. The effects of the solvent and of substituents in positions 1, 3, and 4 of the maleimide ring on the energy difference of the isomers were studied. Depending on the substituents and conditions, the equilibrium can shift toward the maleimide or itaconimide form. Further migration of the double bond and cis-trans- isomerism were also considered wherever possible.

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About the authors

A. A. Panov

Gause Institute of New Antibiotics

Author for correspondence.
Email: 7745243@mail.ru
Russian Federation, Moscow, 119021

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Supplementary files

Supplementary Files
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2. Fig. 1. Structure of hymanimides 1a, b and biologically active arylidenesuccinimides 2 and (indol-3-yl)methylmaleimide 3.

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3. Fig. 2. Isomerization of itaconic anhydride 4 to citraconic anhydride 5 and migration of the double bond in (arylidene)succinimides 6a, 7a.

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4. Fig. 3. Structures of isomeric derivatives of maleimide (a) and itaconimide (b).

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5. Fig. 4. General structures of isomeric itaconimides 8–35 (a) and maleimides (b).

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6. Fig. 5. Cis-trans isomerism using the example of 3-benzylidene-4-methylsuccinimide (8a).

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7. Fig. 6. Isomeric N-substituted maleimides and itaconimides 8, 36–38, as well as anhydrides 39 and anions 40.

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8. Fig. 7. Isomers of 3-benzyl-4-(3-methylbut-2-en-1-yl)maleimide 41b.

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9. Fig. 8. Isomeric annelated maleimides and itaconimides.

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