Spectral behavior peculiarities of the carboxyl functional group in iodine encirclement - the case of 2,6-diiodo-3,4,5-trimethoxybenzoic acid

Kolev, Iliyan; Hadzhieva, Nadya B.; Rogozherov, Marin

doi:10.1016/j.molstruc.2020.129303

Cited by 5 publications

(6 citation statements)

References 21 publications

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“…Different to the also related structures of mono-and diiodo-3,4,5-trimethoxybenzoic acids ITMBA and DITMBA•toluene (Kolev et al, 2021(Kolev et al, , 2023, the title compound exhibits no dimeric structure in the solid state (Fig. 2).…”

Section: Supramolecular Featuresmentioning

confidence: 84%

“…2). This contact presumably contributes to the deviation from the dimeric structure as observed in ITMBA and DITMBA• toluene (Kolev et al, 2021(Kolev et al, , 2023. In the latter, the toluene solvent molecule seems to shield the C 6 � system from this kind of interaction, giving rise to a preferred dimeric structure in this solvate.…”

Section: Supramolecular Featuresmentioning

confidence: 94%

“…All of them reveal co-planar arrangements of the benzene rings and hydrogen-bonding interactions. Furthermore, we recently reported on the previously discussed mono-and diiodo-3,4,5trimethoxybenzoic acids ITMBA and DITMBA (Kolev et al, 2021(Kolev et al, , 2023.…”

Section: Supramolecular Featuresmentioning

confidence: 96%

“…Therefore, in the present work, we present a new environmentally friendly method for the synthesis of 2,6dibromo-3,4,5-trimethoxybenzoic acid. Its structure is closely related to those of mono-and diiodo-3,4,5-trimethoxybenzoic acids ITMBA and DITMBA (Kolev et al, 2021(Kolev et al, , 2023.…”

Section: Chemical Contextmentioning

confidence: 98%

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2,6-Dibromo-3,4,5-trimethoxybenzoic acid

Meurer,

Dimova,

Bodensteiner

et al. 2023

Acta Cryst E

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The title compound, 2,6-dibromo-3,4,5-trimethoxybenzoic acid (DBrTMBA), C10H10Br2O5, was obtained by bromination and transhalogenation of 2-iodo-3,4,5-trimethoxybenzoic acid with KBrO3. Like the previously reported 2,6-diiodo-3,4,5-trimethoxybenzoic acid (DITMBA), the structure of the title compound features a catemeric arrangement of DBrTMBA molecules along an endless chain of carboxylic H–carbonyl interactions. A short carbonyl–phenyl contact hints at a possible lone pair(O)–π-hole interaction further stabilizing the chain-like structure over a dimeric arrangement of the carboxylic acid.

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Section: Supramolecular Featuresmentioning

confidence: 84%

Section: Supramolecular Featuresmentioning

confidence: 94%

Section: Supramolecular Featuresmentioning

confidence: 96%

Section: Chemical Contextmentioning

confidence: 98%

See 2 more Smart Citations

2,6-Dibromo-3,4,5-trimethoxybenzoic acid

Meurer,

Dimova,

Bodensteiner

et al. 2023

Acta Cryst E

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“…In the course of our previous researches, we were able to obtain two iodine-containing aromatic, derivatives of eudesmic, acids -2-iodo-3,4,5-trimethoxybenzoic (ITMBA) and 2,6-diiodo-3,4,5-trimethoxybenzoic acid (DITMBA) (7,8). In both cases, however, the most aggressive iodinating reagent possible -I 2 /AgOOCCF 3 couple -was used.…”

Section: Resultsmentioning

confidence: 99%

Convenient method for one-pot synthesis of novel amidotrizoic acid radioisosteres

Hadzhieva,

Kolev

2022

Scripta Scientifica Pharmaceutica

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INTRODUCTION:The present study presents an effective one-pot protocol for the synthesis of triiodosubstituted aromatic (benzoic) acids -radiopaque analogues of amidotrizoic acid. For the production of the acids intended, I 2 /AgNO 3 couple was used as an effective iodinating reagent. Moreover, suitably substituted methoxybenzoic acid derivatives were selected as appropriate targets for iodination. The total iodine content in the final (crude) products was determined by Volhard's titrimetric method. Further details on the chemical structure of the reaction products were obtained by ATR-FTIR and 1 H NMR spectroscopy. AIM:The aim of the present study is to evaluate the effectiveness of a new method proposed for the synthesis of triiodo-substituted aromatic acids -analogues of the X-ray contrast amidotrizoic acid. MATERIALS AND METHODS:All necessary reagents and solvents for the study were purchased from Acros Organics, Fisher. The syntheses were performed under mild conditions using standard laboratory equipment. The infrared (IR) spectral instrument was a TENSOR II of Bruker (Germany), equipped with an ATR (Platinum) attachment. The total iodine content of the crude reaction products was assayed by a classical pharmacopoeial method. RESULTS: All aromatic acids were successfully iodinated with the reagent couple used. Unfortunately, it was found that the reaction products were mixtures of several compounds -partially and completely iodinated products. The presence of 2,6-diiodosubstituted acids in them was established by the appearance of a ν(C=O) band in the shortwave range (at over 1700 cm -1 ). The total iodine content in the final (crude) products was determined by Volhard's back titration method. CONCLUSION: The applied synthetic method allows the production of a mixture of partially and completely iodinated products, derivatives of the utilized aromatic acids -3,4-dimethoxybenzoic (3,4-DMBA) and 3,5-dimethoxybenzoic acid (3,5-DMBA). The presence of 2,6-diiodosubstituted acids in the products' composition was determined using ATR-FTIR spectroscopy. The reduced yield of the totally substituted products was associated with the lower activity of the iodinating reagent. However, the iodine content of one of the products thus obtained was found to be close to the expected triiodine one.

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