PMID: 11925240Apr 2, 2002Paper

Substituent effects on the thermal cis-to-trans isomerization of 1,3-diphenyltriazenes in aqueous solution

The Journal of Organic Chemistry
N ChenNavjot Chahal

Abstract

The thermal cis-to-trans isomerization of some symmetrically p,p'-disubstituted 1,3-diphenyltriazenes has been studied by means of laser-flash photolysis techniques. The geometric isomerization is catalyzed by general acids and general bases as a result of acid/base-promoted 1,3-prototropic rearrangements. Acid catalysis becomes more prominent as the electron-donating character of the para substituent increases, while base catalysis becomes more important as the electron-withdrawing character of the para substituent increases. In addition, the rate ascribed to the interconversion of neutral cis rotamers through hindered rotation around the nitrogen-nitrogen single bond is found to decrease as the electron-withdrawing character of the para substituent increases. Rates of interconversion of neutral cis rotamers are also found to decrease with decreasing solvent polarity, which is indicative of the involvement of a polar transition state. On the other hand, kinetic investigations of the acid-catalyzed decomposition of target triazenes are consistent with an A1 mechanism.

References

Oct 24, 2001·The Journal of Organic Chemistry·Bogdan StefaneSlovenko Polanc
Oct 25, 2001·The Journal of Organic Chemistry·Ana M. SanchezRita H. de Rossi

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Citations

Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Mohammad Kazem RofoueiSaba Razi Kazemi
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Mohammad Kazem RofoueiJafar Attar Gharamaleki
Dec 27, 2011·Acta Crystallographica. Section E, Structure Reports Online·Mohammad Reza MelardiHadi Amiri Rudbari
Jun 16, 2006·The Journal of Chemical Physics·I Fdez GalvánM F Ruiz-López
Jan 13, 2009·The Journal of Organic Chemistry·Jinlong FuMónica Barra
Jul 21, 2006·The Journal of Physical Chemistry. B·I Fdez GalvánM F Ruiz-López

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