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Unique charge-separated intermolecular and eight-membered intramolecular H-bonds in bis-(thio)barbiturates |
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| Authors: | Nader Noroozi Pesyan Mohammad Jalilzadeh Nasim Yalabi Torkaman Ertan ?ahin |
| Institution: | 1. Department of Chemistry, Faculty of Science, Urmia University, 57159, Urmia, Iran 2. Department of Chemistry, Faculty of Science, Islamic Azad University, Ahar Branch, Ahar, Iran 3. Department of Chemistry, Faculty of Science, Tabriz Payam-e-noor University, Tabriz, Iran 4. Department of Chemistry, Faculty of Science, Atatürk University, 25240, Erzurum, Turkey |
| Abstract: | Reaction of symmetrical and unsymmetrical (thio)barbituric acids with aldehydes in the presence of triethylamine afforded a new form of bis-(thio)barbiturate containing charge-separated inter- and eight-membered intramolecular H-bonds. The reaction products were obtained as bis-(thio)barbiturates containing eight-membered intramolecular H-bond in the presence of l-(+)-tartaric acid (TA). The intramolecular H-bond strength (kcal/mol) and corresponding pKa value for 4ab′ were estimated to be 37 kcal/mol and ?1.3, respectively. |
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