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Paper Information

Journal:   JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS)   FEBRUARY 2014 , Volume 11 , Number 1; Page(s) 35 To 45.
 
Paper: 

UNIQUE CHARGE-SEPARATED INTERMOLECULAR AND EIGHT-MEMBERED INTRAMOLECULAR H-BONDS IN BIS-(THIO)

 
 
Author(s):  NOROOZI PESYAN NADER*, JALILZADEH MOHAMMAD, YALABI TORKAMAN NASIM, SAHIN ERTAN
 
* DEPARTMENT OF CHEMISTRY, FACULTY OF SCIENCE, URMIA UNIVERSITY, 57159, URMIA, IRAN
 
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.

 
Keyword(s): BARBITURIC ACID, NEGATIVE CHARGE-ASSISTED H-BONDS, RESONANCE-ASSISTED H-BONDS, EIGHT-MEMBERED INTRAMOLECULAR H-BOND, L-(+)-TARTARIC ACID
 
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