Unique charge-separated intermolecular and eight-membered intramolecular H-bonds in bis-(thio)barbiturates

Pesyan N. N., Jalilzadeh M., Torkaman N. Y., ŞAHİN E.

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, cilt.11, sa.1, ss.35-45, 2014 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 11 Sayı: 1
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1007/s13738-013-0273-x
  • Dergi Adı: JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.35-45
  • Atatürk Üniversitesi Adresli: Evet

Özet

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.