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  • Synthesis, molecular and crystal structures of 4-amino-3,5-difluorobenzonitrile, ethyl 4-amino-3,5-difluorobenzoate, and diethyl 4,4′-(diazene-1,2-diyl)bis(3,5-difluorobenzoate)
Title: Synthesis, molecular and crystal structures of 4-amino-3,5-difluorobenzonitrile, ethyl 4-amino-3,5-difluorobenzoate, and diethyl 4,4′-(diazene-1,2-diyl)bis(3,5-difluorobenzoate)
The crystal structures of two intermediates, 4-amino-3,5-difluorobenzonitrile, C7H4F2N2(I), and ethyl 4-amino-3,5-difluorobenzoate, C9H9F2NO2(II), along with a visible-light-responsive azobenzene derivative, diethyl 4,4′-(diazene-1,2-diyl)bis(3,5-difluorobenzoate), C18H14F4N2O4(III), obtained by four-step synthetic procedure, were studied using single-crystal X-ray diffraction. The molecules ofIandIIdemonstrate the quinoid character of phenyl rings accompanied by the distortion of bond angles related to the presence of fluorine substituents in the 3 and 5 (ortho) positions. In the crystals ofIandII, the molecules are connected by N—H...N, N—H...F and N—H...O hydrogen bonds, C—H...F short contacts, and π-stacking interactions. In crystal ofIII, only stacking interactions between the molecules are found.  more » « less
Award ID(s):
1933487 2122108
PAR ID:
10526600
Author(s) / Creator(s):
; ; ; ;
Publisher / Repository:
Wiley
Date Published:
Journal Name:
Acta Crystallographica Section E Crystallographic Communications
Volume:
80
Issue:
8
ISSN:
2056-9890
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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