Self-Complementary Dimers of Oxalamide-Functionalized Resorcinarene Tetrabenzoxazines
Dzolic, Z., Beyeh, N. K., Cetina, M., Turunen, L., & Rissanen, K. (2018). Self-Complementary Dimers of Oxalamide-Functionalized Resorcinarene Tetrabenzoxazines. Chemistry: An Asian Journal, 13 (2), 164-169. doi:10.1002/asia.201701426
Published in
Chemistry: An Asian JournalDate
2018Discipline
Orgaaninen kemiaCopyright
© 2018 Wiley-VCH Verlag GmbH & Co. This is a final draft version of an article whose final and definitive form has been published by Wiley. Published in this repository with the kind permission of the publisher.
Self-complementarity is a useful concept in
supramolecular chemistry, molecular biology and polymeric systems.
Two resorcinarene tetrabenzoxazines decorated with four oxalamide
groups are synthesized and characterized. The oxalamide groups
possessed self-complementary hydrogen bonding sites between the
carbonyls and amide groups. The self-complementary nature of the
oxalamide groups resulted in self-included dimeric assemblies. The
hydrogen bonding interactions within the tetrabenzoxazines give rise
to the formation of dimers, which are confirmed by single crystal Xray
diffractions analysis and supported by NMR spectroscopy and
mass spectrometry. The self-included dimers are connected by
numerous and strong intermolecular N-H···O and C-H···O
hydrogen bonds supplemented with C-H···p interactions, forming
one-dimensional polymers, which are then further linked into threedimensional
networks.