3,3’-(4,11-Bis(4-(trifluoromethyl)benzyl)-1,4,8,11-Tetraazacyclotetradecane-1,8-diyl)dipropanenitrile
Round 1
Reviewer 1 Report
Comments and Suggestions for Authors
As stated by the Authors, it is known that trans,transR2R'2Cyclam have been scarcely reported in the literature. Therefore, the synthesis and characterization of new compounds belonging to this family of macrocycles is an interesting topic.
In the present work, the already known compound 1 was prepared as previously described (ref. 6) and then submitted to 1,4-conjugate addition in the presence of commercially available acrylonitrile to afford the desired compound 2 in moderate yield (58%). The latter was carefully analysed by 1H, 13C and 19F NMR as well as IR spectroscopy. Moreover, single-crystal X-ray diffraction was also performed. This analysis allowed to prove the formation of non-classical CH-N hydrogen bond. Unconventional antiparallel nitrile-nitrile interactions and unusual pi-stacking interactions were observed. These behaviours were responsible for the tridimensional arrangement of the cyclam derivative at a supramolecular level.
The well-written manuscript deserves publication in Molbank after the minor revisions listed below.
1) Scheme 1: the nitrile drawn on the reaction arrow was not the acrylonitrile (there are 4 instead of 3 carbon atoms). However, the structure of compound 2 was correct.
2) Experimental section: the NMR coupling constants must be indicated with one digit after the decimal point (e.g. 7.0 Hz instead of 7 Hz).
3) Experimental section, line 132-133: please write the ppm range of the multiplets at 2.49 and 1.71 ppm.
Author Response
Dear reviewer,
I thank you for the valuable comments and suggestions that allowed the improvement of the manuscript quality. I send you in attachment the revised version of the manuscript with the performed changes highlighted in yellow. I have also corrected and highligthed other minor typos found.
Kind regards,
Luis Alves
Author Response File: 
Author Response.pdf
