Acta Pharm. 65 (2015) 207-213

full paper

Short communication

Thermal analysis of N-carbamoyl benzotriazole derivatives

IVAN KOS^†, TIN WEITNER, SANDRA FLINČEC GRGAC and JASNA JABLAN

jjablan@pharma.hr

¹ University of Zagreb, Faculty of Pharmacy and Biochemistry, 10000 Zagreb, Croatia

² University of Zagreb, Faculty of Textile Technology, 10000 Zagreb, Croatia

Accepted January 18, 2015

Thermal properties of N-carbamoyl benzotriazole derivatives and N,N',N''-tribenzyloxyisocyanuric acid were investigated using thermogravimetric analysis and differential scanning calorimetry. The results revealed a difference between structural analogs of N-carbamoyl benzotriazole derivatives. They seem to be in agreement with the previously proposed formation of N,N',N''-tribenzyloxyisocyanuric acid from 1-(N-benzyloxycarbamoyl) benzotriazole, via an intermediary N-benzyloxyisocyanate acid, during heating. Substantially different thermal properties were observed for structural analogues, 1-(N-methoxycarbamoyl) benzotriazole and 1-(N-ethoxycarbamoyl) benzotriazole. In contrast to N-benzyloxyisocyanate, no corresponding reactions were observed for their decomposition products, i.e., methoxyisocyanate and ethoxyisocyanate.

Keywords: 1-(N-benzyloxycarbamoyl) benzotriazole, 1-(N-methoxycarbamoyl) benzotriazole, 1-(N-ethoxycarbamoyl) benzotriazole, N,N',N''-tribenzyloxyisocyanuric acid, thermogravimetric analysis, differential scanning calorimetry, ATR-FTIR

^† Dedicated to the memory of our dear friend and colleague, prof. Ivan Kos.